Future Applications of AI in Entrepreneurship Education (Yours?)

This presentation explores how educators might help founders—and students—learn to think like scientists with AI as a teaching partner, including teaching AI as curriculum. Inside you’ll find:

• Practical frameworks from the teaching entrepreneurship at Dalhousie, helping launch http://ai2market.ca/, and my own academic research, including a recent randomized control trial ran earlier this month.

• Examples of AI tools for ideation, validation, and prototyping.

• Prompts you can reuse to test hypotheses, simulate customer interviews, and design AI-driven ventures.

(PDF of Slides Here)

The challenge for those that help founders develop - is equipping founders to leverage GenAI's decision-making capabilities without undermining the founder’s development of these same skills?

This is the issue we're going to address through a rigorously designed field experiment. To do it well, we need to build a coalition of those that support founders to collaborate. If that sounds like you, please reach out.

The Current Reality

Leading founders, especially university-aged ones, are ahead of society in adopting AI tools. This lets them generate business plans, pitch decks, and prototypes in hours not years. But what if this speed costs those founders the development of critical business judgement?

A field experiment where entrepreneurs in Kenya were equipped with GenAI found that the high performers improved outcomes, while low performers saw worse outcomes compared to control groups. The key finding: entrepreneurs need to know how to engage AI to benefit from it1.

Findings like this make the work of entrepreneurship educators as dynamic as ever. Helping founders make decisions quickly has never been more important, the tools have never been more widely available, and the unconscious obstacles have never been so prevalent.

What We Know Works

Thousands of entrepreneurship courses have explored the best approaches to decision-making since Harvard launched the field nearly eight decades ago. The best evidence we have says that teaching entrepreneurs a scientific approach to decision-making—forming theories, testing them rigorously, learning from results—significantly improves their performance. This approach is not new, it builds atop methods like the business model canvas, and learn startup with its reliance on hypothesis studies. Importantly though, entrepreneurs trained in the scientific approach out-perform those trained on the business model canvas according to rigorous experimental studies involving 759 firms across four randomized controlled trials2.

Tired of reading the “AI-Slop” that started to appear in my university entrepreneurship capstone, I started teaching the scientific approach myself. It rapidly accelerated how quickly students began to think critically about their business. This led me to double down and have now taught it several semesters in a row. As one student reflected:

Integrating this rigor helps students think critically. But how do we do that while empowering them to move faster using AI tools?

The Challenge and Opportunity

AI is a super power for entrepreneurs, letting them generate business and financial models near instantly. This will be valuable for experienced entrepreneurs with the judgement skills necessary to evaluate outputs. Those new to entrepreneurship however, may not have built such critical thinking in these areas (or they may have atrophied with AI-dependence). We know that left to their own device, founders will use generative AI to confirm existing beliefs, not to challenge them.

In the broader AI in Education domain, there is reason for hope and for pause. Large scale aggregation of studies have found that AI in education leads to significant increases in learning 3. Systematic reviews are acknowledging however, the potential for student over-reliance on AI to undermine critical thinking4. In response to such concerns, Google is optimizing versions of their AI models for learning and showing positive results5.

The Research Opportunity

Perhaps more than any educator given the adoption of AI by founders, entrepreneurship educators need tools for using AI to improve learning. The research we’ll be conducting responds to that by asking: How can we support founders in moving faster with AI but also moving smarter?

With the help of entrepreneurship educators like yourself, we will run a field experiment to train hundreds of entrepreneurs in the scientific approach, and explore how AI-powered training tools designed specifically to teach can help.

The research is informed by my time on both sides of this equation as a founder and educator, wrapped up in my PhD research. Beyond exploring entrepreneurial decision-making myself and with hundreds of founders, I’ve completed rigorous reviews of academic research on this topic (summarized here), and evaluated the latest tools.

After hitting gaps with off-the-shelf training tools, I spent months building an AI tool specifically for entrepreneurship education. It guides entrepreneurs through hypothesis formation, rigorous testing methods, and structured reflection on results. The goal of the AI is to build judgment, not bypass it.

The Ask: Partner on Exploring AI in Entrepreneurship Education

I'm seeking partners from accelerators and university entrepreneurship programs to pilot this AI-powered training tool. The Research Questions We'll Address Together: How can we structure entrepreneurial engagement with AI tools around to improve decision-making abilities?

Here's what participation involves:

For Your Founders:

• Asynchronous training on the scientific approach to decision-making (either as a single sitting, or over a longer period)

• Evidence-based skill development proven to improve performance

• Structured guidance through real decision-making scenarios

For Your Program:

• Direct experience with pedagogically structured AI training

• Detailed, anonymized debrief on findings

• Influence on the implementation

What’s Next

The case has been made, the ethics approvals secured, and the training tool is being tested by pilot groups of academics and founders. Now we need to identify several hundred entrepreneurs or entrepreneurship students to test this with. That will only be possible with dedicated field partners.

The anonymized, aggregate findings from this research will be presented at the Conference on Field Experiments in San Francisco October 10th. We’ll then continue follow-on testing based on these results.

By participating, you're contributing to rigorous research on how entrepreneurship education can evolve with AI while maintaining its core purpose: developing founders' judgment and decision-making capabilities.

Ready to Explore This Together?

If you manage an accelerator or university entrepreneurship program and want to give your founders access to evidence-based, AI-powered training that builds rather than bypasses their judgment, please reach out for a call, send a message, or sign up to have me reach out. We’re ready to go when you are!

Discovery Call to Explore this Work

Have questions but don’t need a call?

Luke DeCoste is a PhD candidate in Organizational Psychology, former founder (CDL/Techstars alumni), and entrepreneurship educator researching how AI can empower founders to develop stronger judgment while building faster.

As part of my PhD in organizational psychology—and building on my experience teaching entrepreneurship and working with accelerators—I recently conducted a literature review on AI in entrepreneurship education. Using AI to help screen and classify over 850 articles, I then conducted full-text review and coding of 54 empirical studies—focusing on how curriculum, learning design, and entrepreneurial theory intersect in AI-enhanced entrepreneurship education.

What emerged was a clear pattern. While AI tools are being adopted widely in EE, they’re mostly reinforcing planning-heavy, predictive approaches—think AI-generated business model canvas and market research. There’s far less attention on approaches grounded in uncertainty, iteration, and adaptation. That’s where I believe the next frontier lies.

In response, I’ve been developed an AI-powered training tool that draws from the review’s findings and core entrepreneurship theories (Blank, 2013; Sarasvathy, 2001; Camuffo et al., 2024). The tool guides aspiring entrepreneurs through scaffolded, stage-based decision-making. It simulates real-world tests, offers AI-generated feedback, and—simulations of hypotheses testing. This tool helps ensure AI isn’t replacing the development of judgment, and instead is used to learn more and build faster with structure that supports their growth.

Check out the audio summary to understand the review’s findings and what we still need to learn about AI in entrepreneurship education.

Running a startup is intense. It demands resilience, self-awareness, and clarity—qualities that coaching strengthens. Research shows that founders who engage in structured coaching improve their confidence, decision-making, and ability to navigate uncertainty.

What is Entrepreneurial Coaching?

Think of it as a space—just for you—to talk through challenges, refine your thinking, and clarify your next steps. Coaching isn’t advice; it’s a guided conversation where you set the agenda, and I help you connect the dots. We use open-ended Socratic questions, challenge assumptions, and explore perspectives—all with the goal of helping you implement what matters most to you. And if you're up for it, we do it while walking in nature.

This coaching is led by a repeat founder who teaches entrepreneurship at Dalhousie University and is completing PhD research on the scientific approach to entrepreneurial decision-making. That means the conversation isn’t just about mindset, well-being, and leadership—it also supports you in making better business decisions, testing assumptions, and strengthening your strategy.

What Founders Say

"To have someone chat with me through the direct, and not-so-direct obstacles of startup life clearly translates to reduced life friction and better self-awareness—so I can perform better even when we aren't able to fit walks in."

"Luke has been there, done that. He helps me weigh options, align decisions with my values, and think through complexity."

"That was magic. You ask amazing questions."

"His interest in what I'm doing is meaningful. He listens deeply and holds space in a way that makes me feel seen and heard."

"What makes this coaching different is that I always leave with something actionable—something I can try right away. Then, on the next call, I get to reflect: Did it work? What did I learn? It adds a level of accountability that’s been really useful for me."

Ready to Try It?

Book a Walk and Talk or Call

What to Expect

• Confidential, founder-led conversations on mindset, business growth, and well-being.

• Flexible sessions—virtual or in-person walks.

• Your goals, your pace. Whether you have a pressing challenge or just need space to reflect, coaching meets you where you are.

For Accelerator Managers

Supporting founders goes beyond business strategy—well-being, mindset, and decision-making are critical to long-term success. This coaching program can be integrated into your accelerator as a structured offering, with bulk sessions available for cohorts.

• Custom Programs: Sessions can be part of a structured program with pre - and post-assessments to measure impact.

• Flexible Delivery: Coaching can be delivered virtually or in-person, individually or in small groups.

• Proven Benefits: Founders gain clarity, resilience, and actionable insights to navigate uncertainty.

If you’re interested in bringing founder coaching to your accelerator, let’s chat.

Ecosystem Collaboration Call

Years into our venture we spent so much time disagreeing that leaving seemed like the only move. 

Changing difficult relationships is hard work, but work can be impossible if you don’t.  

Why Change it? 

Work conflict is common. As many as 85% of employees experience it according to a 5000 person survey1.  Workplace conflict is any disagreement that disrupts the flow of work according to the study’s authors. 

Working on over 50 teams in my life, I’ve experienced workplace conflict a handful of times. It sucks. It is bad for our well-being, as well as that of our teams, and our families. It undermines the organization's mission and takes the fun out of achieving it. 

There is no simple roadmap to addressing workplace conflict, but there are some useful insights from business, neuroscience, and marriage counselling. 

Change the Dynamic

To keep conflict from disrupting our work, we need to address it early. Stanford teams expert Carole Robin argues that small frustrations (what she calls “pinches”) might not be a big deal in isolation. Over time, however, they grow into bigger moments of frustration and emotion (what she calls “crunches”) that are harmful to the working relationship.  

To keep pinches from becoming crunches, we can learn from world-renowned marriage researchers, Drs. John and Julie Gottman. They recommend using repair mechanisms to prevent negativity from escalating out of control. Their marriage lab provides a repair checklist that offers suggestions such as how to apologize or express how you’re feeling. 

Even with a checklist, addressing conflict is uncomfortable. The first step, as I’ve written here, is to clarify what is happening, so you can decide how to respond. 

Change Your Mind  

The most important response is to change our minds. As conflict plays out our minds identify patterns that let us react automatically. This helps us make decisions easier but also makes us more close-minded. After years of arguing what seemed like every point with a co-founder, I stopped listening objectively and started prejudging their actions.

Instead of prejudging, we need to live up to the words of long-time social science researcher and academic, Brené Brown, to “extend the most generous interpretation possible to the intentions, words, and actions of others.” Easier said than done.

Automatic judgements are a real problem if they activate your threat-response system sending you into a state of emotional arousal. With your heart racing and palms sweating you lose a sense of how long you’ve been arguing, say exceptionally harsh things, and struggle to accurately process what is happening.  These are the phone calls that end in hangups, the debates where no one feels heard. These are the nights you think about quitting.

Regulating our emotional arousal system in the middle of such conflict is nearly impossible. If you think you’re in this state, ask for a pause, then mentally focus on the physical sensations of your body such as on your breath, not on the conversation you were having. During a 15 minute break for everyone to calm down, I quickly biked to a lake, threw myself into the cold water, and returned to Zoom better positioned to listen. 

If you’re experiencing anything like this you’ve got important work to do away from the heat of conflict. Mindfulness meditation has been key to helping me notice my mind's patterns so I can respond intentionally instead of reacting automatically. Therapists, psychologists, and coaches can also help you understand your reactivity, which could be driven by old mental maps. Start-up coach Jerry Colonna calls us to ask “What are the fragments living in us, like ghosts in the machine, that need to be noticed, identified in the body, felt, healed so that they stop playing out in our lives?” 

Change it Up as a Team 

Such healing is key to healthy relationships and is a lifelong journey. In the interim, changing the structure of collaboration helps. For example, trusted facilitators can move the conversation forward by challenging positions and naming tensions. Adjusting the team can also help. Can you reduce how often you’re having the same debates by changing reporting relationships or reducing role overlap? 

As a quick way to gain relief, clichéd team-building events can dislodge habitual associations to work. In one collaboration, a colleague’s coding expertise and my lack thereof made it difficult to have productive exchanges. I began to think that they thought every question I asked was stupid. Meanwhile, they seemed to think I was questioning their competence. When the weather swept in on a weekend mountain climb together, I was able to offer support that they were able to accept. It helped restore my confidence in the relationship and probably helped them see how I cared. This points to the importance of just forgetting the drama and getting down to doing some work. 

Change Your Goals

The final change may be the hardest. After years of trying to change a relationship, you may instead need to change the commitment to it. One thing my former co-founder and I agree on is that we probably didn’t need to be so committed to making it work. Changing things earlier could have saved lots of pain.  

Sometimes it is fear keeping us in conflict. Catastrophic thinking has us predicting worst-case scenarios with naïve certainty. It took me years to realize that leaving my own company wouldn’t mean failure. It hasn't. I’ve since found meaningful work on teams that restored confidence in my ability to collaborate well. My former company has been acquired and I’ve co-founded an organization with a former investor. Perhaps most unexpected was the way ending the working relationship is restoring the friendship.

I am happy to again consider my former co-founder a friend. We talk once a quarter and I look forward to a visit. We’ll probably not start another company together. 

Few things are as powerful as aligning with a team that cares about you. Few things are as disorienting as a team struggling to get along.

When a relationship is in trouble, the hardest part is often just understanding what is happening.

What you discover, will depend on the questions you ask.

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What is happening?

Sometimes things seem off from the get-go. Perhaps there was a cryptic heads-up from their former colleague.

Other times, things are fine until the chess pieces move. Organizational shifts can disrupt how well your interests align, and how well you collaborate. In 2019, Formula One’s Lando Norris was a close mentee to his McLaren teammate Carlos Sainz. In 2020 the teammates became spitefully competitive when Sainz declared he would leave McLaren at the end of the season.

When you detect tension, respond with curiosity over judgement. Research has shown we are terrible at understanding what other people think about us. Gut reactions can be driven by paranoia as well as wisdom, so let’s just explore this for a minute.

Before you get too riled up, go for a walk, take a nap, and eat something healthy. After that you can start to explore. 

As you do, investigate in ways that nurture the relationship. For example:

• Ask them open questions to discern what matters.

• “Mirror” what they say to verify you heard them.

• Validate what they say, to ensure they feel heard.

• Build trust by vulnerably sharing with them what you care about.

• Spend time relating outside of the transactional elements of the relationship.

• Play together if you can.

• Do all of this while in nature. 

Things won’t change instantly, so be ready to commit to this for weeks or longer without improvement.

If you start to experience clear warning signs like heated exchanges, information withholding, politics, or people not meeting commitments, something is up. But what?

Is it me?

It is probably best to start by asking how you could be causing the problem. 

Spiritual teachers recognized this centuries ago. Jesus warned us to inspect our own records before throwing stones at the sinner. Buddha offered similar counsel - “To straighten the crooked you must first do a harder thing - straighten yourself.” 

Without even realizing it, we could be the one undermining the relationship. We tend to automatically mimic the approaches that worked for us as children. Growing up in the middle of a pack of six siblings taught me how to build consensus. But I can get irrationally squirrelly when I feel a team is unaligned.

The habitual responses we develop in our younger years are also the root of our unconscious bias. When we grow up in a racist society, we inaccurately associate negative attributes on people that look a certain way.

For us white men, the call to inspect our own actions first is crucial. Our ideals for “good” behaviour are built on norms formed to protect our privilege. It is one thing to decide our white-bro colleague is off base, it is an entirely different thing to reactively blame a racialized woman for how her views make us feel uncomfortable.

Mindfulness meditation has been an insightful tool for seeing my own reactive ways of thinking. By practicing noticing my automatic thoughts in the morning, I’m better able to notice my subconscious scripts in the afternoon. Like in meditation, I can then choose to respond to those scripts with non-judgemental curiosity instead of with blind agreement.

When particularly uncertain about your role, engage a neutral and uninvolved party who can ground or challenge your views.

While questioning our own actions fosters accountability, taken too far it can undermine our confidence, our well-being and our ability to show up productively. If this happens, a coach or counsellor can help you learn to trust yourself again.

Is it them?

If, after considerable reflection, we conclude an other is part of the problem, we might be tempted to ask “why can’t they just be reasonable and act like me?” A more curious and empathetic approach however will deliver better outcomes.  

It is possible our colleagues are healing from, or actively experiencing, trauma. As has been powerfully written in Oprah and neuroscientist, Dr. Bruce Perry’s book, the question may not be “what is wrong with you,” but instead, “what happened to you?” In their book, Dr. Perry shares the story of a child acting aggressively towards a teacher. It turned out the teacher wore the same deodorant as the child’s abusive father. By changing deodorant, the teacher helped the child feel more safe. The subconscious nature of the reaction shows how in some sense, we are all this child, transposing our early experiences unfairly onto others. 

Even if you’re in no place to help them, an understanding of what is behind someone’s actions can help you respond more compassionately.

Is it us?

More often than it being me, or you, it is “us” - oil in tension with water.

It could be conflicting interests - one wants rapid growth, the other moderate expansion.

It could be personality types. Nothing is more frustrating for a detail-oriented person than a visionary with an ill-formed plan. For the visionary, nothing is more disheartening than having to unpack the minutiae of their idea for denting the universe.

Strengthening relationships is complex, but personality tests and clarifying vision, values, and roles can help everyone see how they can better support their colleagues.

It is what you think it is.

As you work to understand what is happening, the important thing to remember is that you have a choice.

You can reactively assume the other is an unmanageable problem.

Or each side can take responsibility for their 100% of the relationship, and commit to understanding what each other needs.

As often in life, when collaborating - whether you think you can, or you can’t, you’re likely right.

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Between those first and final breaths, your time will be short, and your help will be needed. Our world is on fire right now, literally and metaphorically, and we all need to lead. To do so, we must develop our visions for a better world.

Your vision will not just appear. It comes through a commitment to clarify it, from first breath to last.  

To intentionally achieve anything, we need a vision to guide us on how we spend our days and our decades. We need compelling visions to inspire teams to achieve ambitious goals, especially in difficult times.

"If you do not aspire to change something and you don't have a good reason for changing it, you cannot and should not lead," argued leadership experts Brad Jackson and the late Ken Parry. 

A clear vision also helps us spend our lives contributing to societal well-being. As opposed to inadvertently supporting patriarchal, racist, and capitalist institutions that are taking away breath through choke-holds and carbon emissions. 

Aspiration, can also mean “to breathe.” 

Why this is Hard

At first it's not even clear we’re supposed to have a vision. Parents, teachers, and institutions work so hard to have us follow their paths that we require an epiphany to break free. 

To articulate a vision and then achieve it, we have to rewire our brains. Through decades of trying to avoid failure, we forge automatic responses. For example, “Any time I aspire to something, I should stop before embarrassing myself.” Such limiting responses are devastating. But with mindfulness, we can overcome them. 

One of the most established ways to develop mindfulness, is through breathing meditation. When we practice applying a kind, curious attention to our breath, we learn to bring this quality of attention to all of our thoughts. We can also use meditation to cultivate self-compassion, which has been shown to reduce fear of failure, including a fear that your vision isn’t achievable, and shouldn’t be articulated1.

How Vision Develops

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From our first breath, we begin setting and achieving new goals. Under an explosion of neurons in an infant’s brain, ancient fight or flight tendencies interact with our early worlds to give rise to life-long aspirations. "Every man is trying to live up to his father's expectations or make up for their father's mistakes,” wrote Barack Obama. As a friend and mentor of mine has said - our gift to the world is bringing about that which we felt a scarcity of as children.

We must develop awareness of how these early experiences influence us. “Until you make the unconscious conscious, it will direct your life and you will call it fate” Yung famously said.

Again, breathing meditation helps. Trying to focus on our breath in meditation, makes us more aware of our thoughts. This helps us identify how a situation or team make us feel so we can decide whether we want to continue to experience it. It also calms our amygdala, so we react more purposefully, as opposed to out of fear.  

{Try it. Pause. Close your eyes. Take a few breaths while paying attention to the air passing through the tips of your nose. If you notice your mind wandering, be grateful you noticed it, and gently bring it back to the breath. If you want to spend 15 minutes talking through your meditation practice, connect here}. Or check out this post to learn more on how to start a practice.

How Vision is Clarified

Most of us have a sense of what we want, but are so intimidated to achieve it, that we dismiss our desires. This is the genius of “The Disney Method,” a creativity strategy that requires us to play the role of “dreamer” before we can be “realizers” or “critics.” 

Life also provides flashes of insight. An intensely frustrating experience can clarify what we feel the world is missing.  Inspiration from adjacent realms offers insight on our own needs. When you feel such clarity, make time to write it out. Don’t however, expect to feel satisfied on your first attempt. In my experience, perfect clarity never seems to emerge. 

When we are most confused, we can do what countless others have done in this situation - head for the solitude of wilderness. When I am unsure of a decision, I head for a hike that requires me to be present to my feet and the elements, and to stop paying attention to the spinning of my mind. As we move through the wilderness, nature provides metaphors about risk, about pushing yourself, about what you need, and about how to find it. As Henry David Thoreau wrote, “I went to the woods because I wished to live deliberately, to front only the essential facts of life, and see if I could not learn what it had to teach, and not, when I came to die, discover that I had not lived.”

If you’re overcome with indecision, or more difficult yet, feeling hopelessness, seek help. Good friends, mentors, and counsellors can ask simple questions to help you find your voice, and to realize it matters. 

{If I can help, book a call any time here}

How We Spend our Breath

After all this work, sometimes we form our vision, only to change it. Perhaps we choose to change it. Or perhaps that choice is made for us - we set out to tackle a mountain, only to be bested by it. We must then find inspiration to summit a new peak, or recommit to climbing the first. These transitions can be painful, as we spend time in the valley looking up. 

In the end, all we can control is our breath until - we can’t.

In that moment, you will ask, what have I done with my breath?

Thanks for spending time with me today. These pieces are hard won. If you enjoy, please let me know by choosing one of the below:

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Mindful Leadership

Why Leaders Need Self-Compassion

Leading can exhilarate and devastate. Self-compassion helps you choose. Leaders envision new realities. Great leaders propose bold visions, and astonish us by realizing them. As a leader committing to a new reality, you commit to not accepting what is - a recipe for unhappiness. Parker Palmer calls this the “tragic gap” - the space between reality and the…

Read more

5 years ago · Luke DeCoste

My coach was on point. “You don’t have to show up like this,” she was saying - “You have a choice.” 

While it has taken years of effort to be able to choose optimism more regularly, I’m getting there.  

To achieve ambitious goals, we have to embrace the challenges, while also cultivating a belief in a better future. For most of us, optimism takes practice and intentional effort, especially when things get hard. But we need it to problem-solve our way to success, to support others, and to feel okay.

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As unhelpful as it may be, a pessimistic approach is understandable. As a toddler, worrying about negative events helped you avoid them. Now, as an adult, well-trodden neural pathways bias you to think negatively. Like a sled following tracks in the snow, you can turn out of the grooves, but it requires extra effort.  

That is not to suggest blind optimism. Optimism only helps you if it doesn’t distort your sense of reality.  Realistic optimism is the halfway point - “a reality-based belief that the future is positive, due to one’s causal analysis and self-efficacy skills,” according to 10 years of empirical research by resilience training company Adaptiv Learning.1 

The Need for Realistic Optimism

Optimism is particularly hard and particularly important in the face of adversity -  but we need enough belief it will get better to work to make it so. If you’ve lost hope as a leader, you need to do your work to get it back, as people are depending on your commitment to a vision. Getting it back may mean diving into your problem to find a new path - talk to your customers, your voters, or your employees. You may also just need a vacation.

Realistic optimism may mean, counter-intuitively, acknowledging that your goal can not be achieved. Some of history’s greatest victories have arisen from changing course. In 1998, Google’s co-founders tried to sell the company for $1 Million, but apparently no worse off for failing to do so. Martin Luther King Jr. set out to be a Baptist minister but became a social rights activist. The world is better for it. When we constrain our definition of success, we limit our ability to envision a better future. 

Our belief in a better future is also essential to well-being. We take on massive projects to fill a gap in the universe, but also a gap in ourselves. When the project looks doomed, it can have us question our self-worth, setting off a spiral of limiting beliefs. We can become victims, believing we have no agency to create a better future. If this continues for days or weeks, we could be entering depression and may need professional help.

There is a privilege in my argument. For some, constant life challenges make it impossible to be optimistic.  Generations of oppression have taught some to expect negative experiences. This intergenerational trauma requires a deeper form of healing than my privileged pep talk. It requires professional support, and more importantly - a commitment by the privileged to disassemble oppressive structures, including by taking anti-racist, and feminist approaches.

When working with others, and ourselves, we need to be compassionate as change takes place. Realistic optimism’s approach of accepting both the good and the bad helps us relate to others. If someone is weighed down by the negative, you can empathize with their reality - life and work do get hard sometimes. And there is nothing worse when you’re struggling, than someone brimming with optimism. 

Still, as a friend or coach, you can help others by tracking their optimism, and challenging them when things are out of balance. 

Cultivating Realistic Optimism

If we want to turn up our optimism, we need to intentionally work to change our habits, to make new neural pathways in the snow. “We’re trying to increase choice about how we might skillfully respond to difficulty rather than reacting automatically or engaging in habitual automatic patterns that may be harmful or at least not helpful to us,” said Patricia Rockman M.D. in a podcast for Mindful.org2. Rockman is the director of education and clinical services for the Centre for Mindfulness Studies in Toronto. 

Mindfulness has been a significant ally as I worked to cultivate greater optimism. With mindfulness meditation, you train your mind to notice your thoughts and to respond to them non-judgmentally and with curiosity. Practicing this on the cushion each morning makes it easier to notice and to guide the quality of my thoughts throughout the day. It helps me to see the grooves my sled is in, and to purposefully turn out of them.

Research confirms meditation’s ability to promote optimism. Specific compassion meditations strengthen brain circuits that are important for a positive outlook according to research by Dr. Richard Davidson of the University of Wisconsin-Madison and fellow researchers.3

Old habits die hard though, so give yourself an advantage by designing optimism into your life. If you journal regularly, add simple prompts like “what are your strengths?” or “what did you achieve today?” Make time to clarify your vision and your commitment to it through downtime to reflect. Teams also need to do this - through off-site retreats that give a chance to look up from the snow so you can be inspired by the mountain tops.  

As we enter month 20 of a global pandemic, it seems as good a time as any to start this new habit. And to help, I’ll leave you with a question that management scholar Jim Collins asked at the beginning of this pandemic - “How can you engage those around you in the question of how to better embody the idea that we will find a way to prevail in the end? And how can you do a better job of confronting the brutal facts as they are today?”4

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I now design and run randomized controlled trials testing how AI-supported learning interventions affect founder decision-making, and I build the tools to go with them. That work sits at an unusual intersection: field experiments that generate real evidence, paired with software that puts those findings into practice. A through-line in everything I do is evaluation, helping programs, institutions, and organizations understand what actually works, not just what feels right.

I teach entrepreneurship at business schools and accelerators across Canada, and hold an adjunct faculty appointment at Dalhousie University, where I am the Academic Lead for AI2Market. I’m completing a PhD in Positive Organizational Psychology at Claremont Graduate University, where my dissertation focuses on how AI shapes entrepreneurial learning and decision-making.

Over the years I’ve coached dozens of founders on a recurring basis and taught over 1,000 more through university programs, national entreprneuerhsip events, and through AI-aided entrepreneurship education experiments.

What I work on:

- AI-powered learning tools for founders — built and tested through live RCTs with post-secondary institutions

- Entrepreneurship education — workshops, MBA courses, and accelerator programs across Canada

- Program evaluation — helping organizations understand what interventions move the needle for founders

- Coaching — for founders navigating growth, hard decisions, and the harder parts of the startup path

Book a Zoom or Walk and Talk

Client Testimonials:

To hear it from the entrepreneurs I teach:

• “Your method of teaching is phenomenal. You ask the right questions, use the right amount of humour. Super engaging.“

• “The Professor does a great job of assessing what we want to get out of the course and how the course can help meet those goals.”

• “Best course I have taken at Dal to date”

• “I think it was great, I think this was the first class in my whole degree of four years where I got to know so many of my classmates fairly well.”

• “I love the environment of the class, it is very welcoming“

• “Applied Entrepreneurship & Innovation was the most engaging and practical course I’ve taken at Dalhousie so far. We had the opportunity to learn from many different successful entrepreneurs (Including Prof DeCoste), participated in an atmosphere that made meaningful relationships, and learned applicable entrepreneurial skills. If you have any aspirations of being an entrepreneur or are interested at all in entrepreneurial ventures, this class is a must-take!”

Bio Highlights:

My work is informed by constant efforts to help entrepreneurs thrive, including:

• Co-founded and exited several ventures, including proofgov.com (acquired; Techstars, Creative Destruction Lab alumni). Co-founded MindFrameconnect.com.

• Academic Lead, AI2Market, a program designed to accelerate innovation and drive commercial success through AI adoption in Canada.

• Co-chaired a Governor General’s Canadian Leadership Conference Study Tour.

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Most people only discover they don’t know how to lead upon finding themselves leading. And now, charged with inspiring people, they bury their feelings of inadequacy. A healthier path, I now know, is to treat the fear as a sign that learning to lead matters to you and to commit to figuring out how to do it.

Being unsure of what to do is a key step in learning to lead. Most of us are well into leading before we are taught anything about it. We’re called to lead because we’ve performed well as nurses, engineers, marketers, etc, not because we’ve performed well as leaders. And then it is baptism by fire, to the detriment of our well-being and to those we lead.

This setup misses the point that everyone can lead, regardless of their role or title, and it delays many from starting to realize their vision.

Worse, if leadership is inaccurately linked to hierarchy, and our hierarchies are built on racist and patriarchal structures, we are delaying the empowerment of those most limited by these structures, and most incentivized to dismantle them.

Regardless of when you come to it, leadership will be unnerving. As a leader, you courageously hold up your vision for a different future. The world will almost always resist this change, causing you to question whether you know what the hell you are doing. To realize your vision, you have to keep going.

Yet humans are poorly designed for pushing past reasons to quit. Our ancient wiring tries to keep us safe by encouraging us to conform to the status quo. With practice, fortunately, we can choose to focus on our “why,” cultivating courage over fear.

In pushing through the hard, you discover that leading is deeply fulfilling, and key to realizing your vision. So please lead. The world needs what you have to offer.

As you start to lead, a commitment to learning will help you along the way. As I started to lead, biographies of leaders helped me reflect on my leadership. Harvard Business Review articles were a gateway to academic articles on my specific area of interest - mindful leadership. Your curiosity will be a trustworthy guide as you deepen your understanding of leadership.

While “book knowledge” will help, it alone can not make a leader for leadership is as much an art as it is a science. (Even something as foundational as a definition of leadership is not agreed on.)

And so we want to balance the learning with doing - by practicing leadership. Spending time clarifying vision, and bringing about the resources needed to make it possible. Working to inspire people and staying optimistically committed to goals, even when that requires patience and flexibility. Being proactive when you want something - identifying paths to make it happen and consistently moving down these paths.

These are just best practices. Your “how” will be your own. Effective leadership requires an incredible amount of self-awareness and introspection, and a constant reflection on what you think needs to be done, how its going, and how you’re showing up along the way. Each step will give you feedback about how to improve.

That feedback can transform your leadership. Especially if you adopt a Growth Mindset - a belief that you can improve. You’re going to encounter all kinds of situations that you don't know how to handle. If you experience them as insurmountable challenges confirming how little you know, your vision and well-being will suffer. Take them as opportunities to breathe through the challenge, to learn, and to improve however, and you’re ahead no matter the outcome.

Finally, be gentle with yourself. Leading is hard and as I’ve written here, self-compassion helps a lot. This evidence-backed idea has three elements. First, treat yourself with kindness. Second, recognize that suffering and feelings of personal inadequacy are part of the shared human experience of leadership. Third, practice mindfulness by not over-identifying with your thoughts. Not only does self-compassion feel better, it contributes to the development of a Growth Mindset and to greater creativity in achieving your goals.

Leading is important. It's hard. It's worthwhile. And it takes a life to learn it. Best to start now. If you want to talk about any of these ideas, feel free to book a chat here.

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It turns out our brains have a lot to do with it. The mass of meat in our skull kept us alive by playing it safe, not by taking risks.

One way it kept us safe was by developing biases, preferences for certain ways of responding, such as a bias towards avoiding loss. “Loss aversion bias” prevents us from taking even smart risks with the potential for worthwhile gains. This can make us reluctant to ask for what we want out of fear of losing what we have.

This shows up particularly strong through our fundamental desire to belong. This desire goes back to our prehistoric ancestors for whom rejection from the tribe could have fatal consequences. “Belonging is the innate human desire to be part of something larger than us,” says researcher Brené Brown. She continues, “because this yearning is so primal, we often try to acquire it by fitting in and by seeking approval.” I had been feeling this deeply as I prepared to make my ask. I believed I was making an ask that would jeopardize my role on the team.

Our brains aren’t always great at forecasting outcomes though. Cognitive distortions, habitual ways of thinking that are often inaccurate and negatively biased, cause us to create untrue stories about how things could play out. For example, if you’re suffering from “all or nothing thinking” you may fear that you’ll be resented for asking for a raise. In reality you might just be given milestones to hit in order to get that raise. I also know I’m not alone in the regret of sacrificing what I wanted for a “safer” bet that never showed up.

Even if we plan to make the ask, we might delay because of status quo bias, a preference for the current state. This can be quite damaging for our ability to achieve our goals, as we achieve our goals through the patient building of capital. As we age, we lose the desire to build this capital, be it knowledge capital, social capital, or financial capital. While we delay asking, we’re moving to points in our life where we’re less likely to be able to achieve our goals.

Worse yet, delaying the ask could actually be killing you. That desire you feel towards a goal or frustration you feel when you don’t achieve it are important emotional signals. Studies have shown that suppressing such emotions can increase the risk of early death, including from cancer.

How do we ask for what we want?

If asking is hard but worthwhile, how could we make it easier?

First we must overcome our fear. Some easy activities can help us reduce our baseline emotional reactivity to fear. This includes sleeping, exercising, practicing gratitude, and meditating. Professional counsellors can help too, by countering cognitive distortions, and building up your feelings of self worth so you’re more confident making the ask.

Before you make the ask, it is useful to get clear on your “interests.” This is one of the most helpful pieces of advice in Getting to Yes, a Harvard Negotiation Project book that I take out every time I’m making a difficult ask. Interests are the desires and concerns that motivate people. Grounding yourself in the why helps you muster the courage to ask.

To get clear on your interests, ask what you want, and then ask why you want it. This helps you get down to the most powerful interests, which are often basic human needs such as safety and belonging. Beyond helping with the ask, the pre-planning acts as an exposure therapy making the actual ask less frightening.

Finally, be compassionate with yourself. Courage is hard. And you may find yourself frustrated when weeks go by without you asking. If you are too critical you’ll hurt your self-esteem and the likelihood of asking. If you instead practice self-compassion, treating yourself like a friend, you’ll be more likely to recognize your value and feel okay making the ask.

So, if you haven’t yet gotten to it, can I ask you to be gentle on yourself?

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This is meant to be a dense read on mindfulness, its benefits, and its relationship to meditation. I also introduce a simple breathing meditation, give thoughts on how to start a regular practice and on what to expect as you do.  

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Mindfulness and Meditation:

Mindfulness is most simply described as paying attention to the present moment with an attitude of curiosity and kindness. Mindfulness is an innate human capacity which can be strengthened through mental training. This mental training often takes the form of breathing meditation which, through a process known as neuroplasticity, changes the structure of the brain in ways that support the capacity for mindfulness.  

Mindfulness has been shown to boost resilience, strengthen team dynamics, and improve creativity and decision making. From a health perspective, studies have shown that mindfulness may reduce anxiety and depression, enhance immunity, address insomnia, and help manage pain and unhealthy habits. 

Mindfulness is all about the present moment. So whether you’re reading this on a computer or on a train, let’s try a short meditation practice.  

The Practice:

Some guiding thoughts before we begin. 

First, approach this mental training like a physical one. The first time you do a push-up, it will be hard - your form will be off, and you will want to quit. However you stick with it because you know it will make you stronger in the end. 

While exercise strengthens muscles, meditation strengthens your mind by improving the focus and quality of your attention. In this practice you will train with an object that you always have available to you - your breath. You’re simply going to breathe at a natural pace, ideally through your nose on both inhale and exhale. As you breathe, you’ll train your focus by paying attention to the sensation of the breath where it enters the nose.

As you direct your focus, you’ll also practice taking a curious, and kind response to whatever else grabs your attention. And to be clear, especially at the onset, other thoughts will grab your attention. When you notice you are distracted, kindly return your attention back to the breath. Do your best not to scold yourself for getting distracted. Instead, give yourself a mental pat on the back for noticing, and kindly return to the breath. (Noticing and quieting self-criticism during meditation can help you do the same during your day.)

When you begin paying attention to your thoughts, you may revisit experiences you’ve long since buried. It is important to be gentle with yourself. Especially if you’ve lived through traumatic experiences, you will want to be cautious, and consider engaging a trained professional before you begin. 

As you start to meditate, you are likely to have thoughts that make you want to stop. You may decide you need to close a window or make coffee. You may find yourself criticizing the activity or yourself for trying it. Simply notice these thoughts. Thank them for showing up, and again, return your attention to the breath. 

Before you start, help yourself out by turning off distractions like music and cell phone notifications.

Next choose an alert, upright posture, either on a chair or cushion.

Finally, set a timer. Nothing heroic - two or five minutes will be fine introductions.

With the timer set, lower your gaze or close your eyes.

Begin paying attention to the sensation of your breath. Whatever comes up, simply notice it, and then kindly return to the breath. Again. And again. 

When the timer finishes, simply notice how you feel. What did this experience show you about how you should approach the rest of your day?

Moving from an Introduction to a Practice:

While this only took a few minutes, a few things happened here. First, we’re developing our ability to focus, and to respond to everything in our life with kindness and curiosity. Second, we took a moment to calm our nervous system which otherwise may spend a lot of time in a state of reactivity. Third, we took a moment to check in with ourself to see how we’re doing.

While studies have shown benefits from a single session, it will take a daily practice to really unlock personal growth. There are some basic habit-forming frameworks to help with that. I’ve written previously about using BJ Fogg's Tiny Habits model for this. To summarize: 

• Motivation - increase your motivation. You can do this reading on mindfulness (for example on how to meditate at mindful.org). You can also lock in motivation by journaling on how each meditation felt. 

• Ability - increase your ability. You can do this by keeping sessions short at first. Many people dive in and want to do hours. After 3 years I have settled on 10 minutes a day. Sometimes twice if I can find the time.  Apps will also help (e.g. CALM, Headspace, or Insight Timer).  Reading above will also help. 

• Prompt - set prompts to meditate. For example place a meditation cushion in a place you will see it at the time of day you want to meditate. It can also help to bundle your meditation session with another activity. For example, I wake up, turn the kettle on ahead of coffee, and then meditate. I never have to think about when I’ll do it because I always do it then.

As your streak goes from days to weeks, to months, you’ll notice new and deepening benefits. You may notice the emotions or thoughts that arise in particular situations and choose to avoid those situations. It can be quite powerful. But as I’ve written elsewhere, bad days don't go away with mindfulness. They are just rarer, easier, and shorter. 

That’s it. Just start. Yes it's hard at first, but so are most worthwhile things. While you probably don’t have time, meditation has a way of helping you understand where you’re wasting time by habitually doing things that you don’t need to do.  If you fall off the streak, don’t abuse yourself, just kindly return to the breath. Again. And again. 

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Bad days don't go away with mindfulness. They are just rarer, easier, and shorter. It's not eternal bliss. It's a sort of equanimity - a calm composure in good times or bad.

I’ll take it.

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My difficulties were minor, but the mind has an ability to find trouble when it wants to. After attending my first wedding since the pandemic started, I woke up with enough wedding cake in my blood stream to make me unfit to drive. And I was irritated by a lack of sleep, especially since I was giving an important presentation that morning (appropriately on mindfulness).

The presentation went well, but pre-presentation stress was compounded by technology challenges. By the time it was done, I was done; sleep-deprivation and stress met the feeling of completing an important task imperfectly.

As mental chatter was kicking up negative emotions, the positive habits I was cultivating through mindfulness also began kicking in.

Countering Cognitive Distortions:

On noticing the negative, I began countering unhelpful thoughts. Psychologist Rick Hanson has argued that the brain is teflon for good and velcro for bad. This is even truer in times of sadness. It becomes important to counter what are called “cognitive distortions,”- unhelpful ways of thinking. This is a basis of cognitive behaviour therapy.

There are a number of recognized distortions to counter. For example, your mind may jump to:

“All or nothing thinking” such as concluding if I didn’t do it perfectly, I have failed;

“Over generalizing” by unreasonably seeing a pattern based on a single event; or

“Magnification” by blowing things out of proportion.

There are a number of critical questions you can ask yourself or journal on to expose distortions. E.g. Is this thought 100% true? Is it exaggerated or irrational? Are there any other perspectives I’m ignoring?

These efforts were useful and by the end of the day, I was gaining perspective.

Deploying Self-Care:

A second key response was letting myself off the hook and making way for self-care. Instead of frustrating or shaming myself, I put my laptop away for a bit and launched into some proven approaches to self-care.

Practicing Mastery: Simple mastery can be a confidence builder, and a better use of time than moaning, so I did some laundry. At some point I made matters worse with an ambitious meal plan that didn't fit within the time constraints of a pending daycare pickup. I forgot the importance of dropping the A+ mentality and accepting B- in these moments.

Directing Attention: Eventually I put on Netflix. I was surprised to find watching movies a recommendation in mindfulness literature. Sensory experiences can help you put your attention on something else. (Think about how to bring a crying baby to joy - tickles, treats, or Dora)

Asking for Help: Beyond being kind to myself, I also asked for kindness from those nearest to me. While I try to not burden others with my shit, it can be useful for them to know when your resilience is low, so they can treat you with compassion. Sleep-deprived herself, my wife did her best to be gentle.

Sleeping Well: Finally, we planned an early evening. Like 8pm early. Fortunately our toddler complied. Cue heavenly angel sound effect. Sleep is critical to well-being and completing stress cycles.

Between self-care and countering cognitive distortions I pulled out sooner, and with less self-induced pain than a previous version of myself would have. It's not that it didn’t suck. And it required a persistent effort to cultivate positivity. But that's the value of mindfulness; not eternal bliss, but ease.

As the Buddha has said, “In life, we can’t always control the first arrow. However, the second arrow is our reaction to the first. The second arrow is optional.”

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Leaders envision new realities. Great leaders propose bold visions, and astonish us by realizing them.

As a leader committing to a new reality, you commit to not accepting what is - a recipe for unhappiness. Parker Palmer calls this the “tragic gap” - the space between reality and the better world you know is possible. While you must do your work to help stay positive, hard things are hard, your mind has a negativity bias that struggles with uncertainty, and reality's stubbornness tests even the most resilient leaders.

When executing a difficult mission, you relentlessly seek areas to improve, including your own performance. Trouble arises when such self-reflection descends to harsh self-judgment; when “How come I can’t make it happen?” turns to “What the hell is wrong with me?”

While self-reflection is essential to high performance, balance is needed. Harsh self-judgement activates our biological threat detection system, increases stress hormones, reduces our willingness to trust, and restricts our ability to process information clearly. All unhelpful when trying to put a dent in the universe. Plus, self-flagellation just feels shitty and can lead to depression.

How Self-Compassion Helps

Recent research is confirming the benefits of an ancient, kinder response - self-compassion.

In contrast to self-judgement, self-compassion deactivates the threat detection system, and activates the care system. The care system releases oxytocin ( the love hormone), which reduces stress, and increases feelings of safety. This helps you be present in the moment and free to make decisions guided by rationale and not fear.

What exactly is self-compassion? In 2003, a leading researcher on self-compassion, Kristin Neff at the University of Texas, wrote “Self-compassion entails three main components: (a) self-kindness—being kind and understanding toward oneself in instances of pain or failure rather than being harshly self-critical, (b) common humanity—perceiving one’s experiences as part of the larger human experience rather than seeing them as separating and isolating, and (c) mindfulness—holding painful thoughts and feelings in balanced awareness rather than over-identifying with them.”

You might be thinking, if I’m not making the progress I want, shouldn’t I ruthlessly criticize myself instead of taking a warm bath of self-love? Actually, no.

New research continues to show how self-compassion improves performance, including by motivating you to change. For example, self compassion:

• Encourages Self-Development: Based on her research, Dr. Serena Chen has argued in the Harvard Business Review that self-compassion helps you more accurately evaluate your own performance. She also found it builds motivation to improve on such weaknesses.

• Enhances Creativity: A 2010 study published in the Creativity Study Journal found that individuals with relatively high self-judgment who were exposed to a self-compassion journaling exercise had higher levels of creative originality than the control group who did not do the journaling.

• Improves Resilience: In a series of studies published in the Journal of Personality and Social Psychology, it was found that self-compassion reduced defensiveness, and increased resiliency.

• Reduces Fear of Failure: Research published in Entrepreneurship Theory and Practice in 2019 found that entrepreneurs exposed to a meditation that generated self-compassion had lower fear reactivity. Lower fear reactivity promotes clearer thinking, and an ability to act.

Beyond the research, I’ve personally experienced the benefits of developing self-compassion. A consistent meditation practice helped me become aware of self-critical thoughts that were unsupportive, especially in the entrepreneurial domain. I now find myself weekly pulling out self-compassion exercises that help me focus on my work, instead of my worries. I’m also using it to calm the mind when having trouble sleeping.

Neff’s three elements of self-compassion above offer guidance for deploying it yourself. First, acknowledge your thoughts, but don't identify with them. Second, recognize that you're not alone in your struggle and that others experience challenges not dissimilar to yours. Finally, reflect on what a kind response to your troubles may be, or what a friend may suggest for you.

For explicit self-compassion exercises, Kristin Neff has a number of resources including meditations and journaling exercises here. I also regularly use Tara Brach’s self-compassion based “RAIN” practice in moments of overwhelm.

Leading can be difficult. Reality can be stubborn. Don't beat yourself up over it.

While New Years has long been a time for new habits, this one provides a unique chance to begin meditating.

The popularity of starting new habits with “Temporal Landmarks” like the start of a new year was confirmed in a 2014 study. Researchers from the Wharton School of the University of Pennsylvania found that google searches for the word “diet” increased by 80% on January 1st.

The authors of this paper argued that milestones like the beginning of a year help mark the passage of time, creating new mental accounts, or “clean slates”. In doing so, these landmarks “relegate past imperfections to a previous period, induce people to take a big-picture view of their lives, and thus motivate aspirational behaviours.” If there was ever a year to relegate to the past, it is 2020.

If you are going to invest in one new habit this year, why choose meditation? For me, it has been a keystone habit that helped me improve many areas of my life. The strongest endorsement I can give is to still be meditating daily more than three years later ( described here). Beyond my personal take, thousands of studies have shown mindfulness meditation improves mental and physical health, including by improving sleep, creativity, relationships, and stress management.

A new year is also, for many of us, surrounded by the down-time needed to put in the hard work of moving from willpower-driven goal to automatic habit. For better or for worse, this Xmas holidays will have even more down-time. We’re spending less time travelling, shopping at malls, and hosting massive dinners. This will give you the time and space to set up a meditation routine, and start to see the benefits.

Reflecting on the past year, as many of us do over the holidays, should increase your motivation to meditate. The holidays will be a first chance to reflect on a year of worries that were coupled with a loss of access to resilience-builders like exercise and social activity. 2020 was a year when meditation paid dividends.

And while vaccines give reason for optimism, anyone predicting a stress-free 2021 should be asked about the accuracy of their 2020 predictions. Then I’d suggest they not count their chickens before the minks show up.

If you are on side to start meditating this January, here is an introduction to getting started and building a consistent practice. Specifically, increase your motivation through reading about the benefits. Then increase your ability by learning the methods, adopting tools, and starting with short sessions. Finally, set up lots of prompts, make a meditation space, and pick a consistent time. And if all else fails, don't wait until January 1st 2022. Instead, create a new temporal landmark out of February 1st and try again.

At least to someone who designs behavior change like Dr. BJ Fogg.

Fogg Behavior Model

Fogg, known as the founding father of behavior design, spent the last 20 years studying human behavior at Stanford. According to Fogg’s Behavior Model, three things have to happen at once for a behavior to take place: a prompt, an ability, and a motivation.

I’d like to think my three year meditation streak was the result of sheer grit. Fogg’s Behavior Model however shows it was the result of strategically timed prompts, ability-changes, and motivation spikes.

Let me elaborate.

Motivation:

Without realizing it, my motivation to meditate was increasing before I started any routine.

For example, a year before taking on a daily practice, I started a company. Start-ups are stressful. Meditation was a well-known tool for managing stress. My motivation to meditate increased.

Then, three months before starting a daily meditation practice, I was introduced to a simple mindfulness exercise by our company’s executive coach, Urszula. With her encouragement, I began a daily exercise that included taking five breaths, focusing on a different sense with each breath, and then journaling on three questions: 1) How do you feel? 2) What did this practice allow for? 3) What did you discover about your day?

This 30-second exercise made me aware of thoughts like, “there's a lot going on.” This awareness motivated me to meditate. I also began to see the value of mindful pauses. “This practice has been really helpful. I’m feeling calm,” I wrote early on.

Unlike many healthy habits, when I meditate, I want to meditate more. In contrast, flossing my teeth doesn’t make me want to floss my teeth. When I began meditating, I was simply chasing a 30-day run. By 1000 days, I was journaling “this practice has healed me immeasurably.” (I elaborate how here). This positive experience of meditation helped keep my motivation high.

Ability:

Ability is the next requirement of behavior change in Fogg’s Model. The model identifies three ways to increase ability: 1) training, 2) obtaining a tool that makes it easier, and 3) scaling the task back. I benefited from all three.

To train, I was studying books like Search Inside Yourself (by Google’s Jolly Good Fellow - Chade-Meng Tan), podcasts from Reboot.io (a coaching company led by a long time meditator), and from teachers at a local meditation centre.

Two tools increased my ability to meditate: 1) Urszula’s mindfulness exercise described above, and 2) Calm’s meditation app, which offers a free “7 days of calm” program, which I did back to back three times in my first 21 days of meditating.

You can also increase ability by making something easier. The five breath practice explained above was so simple I started meditating without knowing it. From there, scaling up to 10 and then 20 minute meditations was easy.

Prompt:

The final component of the behavior change model are prompts. As Dr. Fogg writes here, “Without a prompt, the target behavior will not happen. Sometimes a prompt can be external, like an alarm sounding. Other times, the prompt can come from our daily routine.”

I was swarmed by prompts. Each time I noted stress in the five breath practice, I was prompted to meditate. When I consumed new information on meditating, I was prompted to practice.

Regular routines also prompted me. Morning meditations help clarify my day, so I began meditating each morning. Soon, simply getting out of bed prompted me to meditate. I was also prompted by the arrival of each Sunday morning, which was when the local meditation center had free drop-ins.

Finally, my environment prompted me. I left a cushion out that I meditated on. When I saw it, I was prompted to reflect on whether I had meditated yet or not.

Conclusion:

If you're starting your meditation journey, and want to talk through it, reach out any time. Even though I’ve done it, I don’t know how. It is impossible to think I could add a 10 or 20 minute activity to my day and do it daily for three years and counting. Clearly I should be more mindful.

I can’t think of a stronger endorsement, than to have meditated again today.

This started out of desperation. My mind was no match for my life. Start-up stress and a lingering concussion were conquering my happiness and self-worth. I had dabbled with meditation until then, but only when a mentor hit 800 days, did I decide I could do at least 30.

In the first weeks, I noticed something. My thoughts. Specifically, negative self-talk. It was the beginning of a transformation from self-flagellation to self-acceptance, as I went from noticing the chatter after it happened, to noticing it as it happened, and to eventually just not doing it at all.

Changes were also occurring in my relationships with others. Conversations with the people I loved would be blown up by Amygdala Hijacks - “a personal, emotional response that is immediate, overwhelming, and out of measure with the actual stimulus because it has triggered a much more significant emotional threat (Wikipedia).“ You may know it as “losing it.” The Hijack then escalates others, resulting in both sides saying things they would never say under calmer conditions. Now however, I notice when I’m agitated, and can de-escalate before things derail.

Daily focusing on my breath is practice for focussing on others. I just listen way better now. Sometimes a word or two into an unneeded pronouncement, I’ll pivot to asking the person an open question. No one has complained with more interest being taken in their life.

On the macro level, I better notice when I’m stressed, or tired, and can respond by giving myself the care I need to show up well for others.

But as a multi-decade mindfulness leader said - the best way to know if it's working, is to ask those around you.

Well. My wife says she was proposed to by a 7, but married a 9. That’s interesting...

A former business partner said “I think he knows, but he may not really know just how much he's changed. He used to be a hustler and now he's basically a zen master.”

And a new friend and colleague messaged me recently to say - “you are so calm. It’s tremendous.” This would be shocking to someone who knew me a decade ago.

If there’s one thing I’ve learned from meditating over the last three years, it is that you are not your thoughts. You can change your mind, your character, and your life.

It’s hard to know what would happen if I stopped meditating. But honestly, I have no intention of finding out.

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P.S. A next post will talk about the lessons learned on maintaining a regular practice. Stay tuned if interested, or reach out any time to talk about starting your meditation journey.

There are definitely going to be obstacles ahead. If you focus on them, they’ll win.

Focus instead on clarifying your vision, celebrating what you’ve achieved, and taking the next step.

The rest is out of your hands.

This is one of a number of ideas prompted from a journey of having coffee with 75 of 2020's Disruptive Leaders.

On exiting my start-up this summer, I was asking myself that same question. Trying to convince myself I had a plan, I found myself saying “I’m going to have 50 coffees and go from there.”

In hindsight, it was brilliant.

On park benches, zoom links, and sandy beaches, 75 people shared visions inspiring and challenging them.

A few of these people were freshly tossed into leadership and are breathing deep into what they have to pull off. A newly minted not-for-profit CEO is charting a course into unknown economic viability. A new-media leader worries about her team’s well-being while herself carrying the weight of disrupting a troubled industry.

Some have clear visions for what they are trying to create, accompanied by real fears about whether they’ll get there. A tech CEO is so concerned with achieving his ten year vision, that he barely blinks at winning entrepreneur of the year. A social-enterprise builder is reflecting on how his values are challenged by launching a for-profit company. And a young Executive Director describes a “swing for the fences” vision for protecting Canadian’s data.

Others are in that messy middle questioning their resolve. A politician staring an election in the eye asks - am I ready to pursue this? While a public servant exhausted by resistance to change searches for inspiration.

Finally others, like me, are painting a new slate. An executive coach is ready to leave her company to create something new. She is more subdued than an innovation leader plotting new ways to achieve her maximum utility, even if that means breaking some things.

If I learned something from these coffees, it is that changing the world is a journey, not an end-state. You are not the title you hold, but the commitment you make to constantly clarifying your vision, and to caring about yourself and those around you as you fulfill that vision. While I now feel more grounded, my appetite for coffees has only strengthened. If you need one yourself, book one any time.