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How Therapy Made Me a Better Entrepreneur

There is something most entrepreneurs don’t appreciate about opportunity.

Everybody running their own business understands how important capitalizing on the right opportunity, at the right time, is. A premature opportunity goes nowhere, while an opportunity leveraged by many others becomes difficult to exploit.

The really interesting thing about opportunity is that most people do not recognize it in each and every moment, because they do not recognize what opportunity is really all about.

Opportunity is about understanding people, their motivations, behaviours, goals, needs, and desires. The best opportunities come from understanding, within a specific context, people in a way that nobody else has understood them before.

And it’s not just about the opportunities that initiate entrepreneurial effort. When running a business, opportunities permeate reality!

Everything contributes towards the ultimate goal of the business. Every conversation with clients, partners, stakeholders, contractors, and employees, all of them are opportunities to encourage, inform, negotiate, and strengthen relationships. Every email, every advertisement, and every hire — they are opportunities to extend the reach of a business. Every success is an opportunity to leap further forward, and every setback is an opportunity to learn.

So if entrepreneurship is all about taking advantage of opportunities, how exactly do we do that? How do we better understand our fellow human?

Having done the work myself, I believe that learning about how the mind works is one of the most effective ways to understand people. I also believe that therapy is one of the best ways to do that. Allow me to convince you that you should consider seeing a therapist to improve your entrepreneurial instincts, regardless of how satisfied you are currently with your mental health and overall life experience.

Learning About Yourself

Have you ever been surprised by the way you reacted to something?

During one particularly stressful engineering team meeting for a company I once consulted for, I was listening to the leaders discuss the viability of some large upcoming projects. Every time the CEO asked the engineering leads whether something was doable in a given timeframe, the answer was some variant of “yes”.

“What are the risks associated with these projects?” I’d interject. I knew very well that the promises the engineering team made would get translated into promises about upcoming features the company’s clients could expect, and within the timeframes being discussed to boot. It seemed unlikely that we could get everything done in the next quarter, or even the next year.

“The purpose of this meeting isn’t to discuss the details, it’s to plot a course and determine whether it is possible.” responded one of the engineering leads. This seemed to satisfy the CEO. Meanwhile, I was incredulous — how can you know whether something is reasonably possible without understanding the risks involved? Isn’t it the responsibility of the team who will build out a project to alert leadership to potential problems? What other reason is the entire engineering team in the room for?

I kept detailed notes of everything I could foresee being a problem through the rest of the meeting, saying very little. Shortly after, I walked into the CTO’s office to voice my concerns.

“That meeting was a total waste of time.” I started. I handed him my list of concerns and pitfalls. “Your engineering leads are taking you down a path to disaster, and the engineers clearly don’t have the confidence to speak up. Tread very carefully.”

I realized as I drove home that day that I had not communicated nearly as effectively as I could have. It was the delivery that was problematic, because my reasoning was lost in the passion I felt in the moment. And honestly, this wasn’t behaviour I hadn’t observed and discussed with leadership before, so why had I been so incensed?

My therapist had an idea when I asked about it. “It sounds to me like you were angry, and understandably so.”

“Why is it understandable?” I could almost feel my frustration mounting again. “I’ve seen this behaviour a thousand times, here and elsewhere. I should have remained a little more composed to make my point more clearly. The anger wasn’t helping anybody.”

“I would be pretty unhappy too if my insight and concerns were ignored, even if my reputation wasn’t on the line, like yours is! And, I also think your anger is helping you.”

“Yeah?” I responded, disbelievingly. “How’s that?”

“It’s telling you something is wrong.” My therapist would go on to explain to me that every emotion has a need (or needs) attached to it. “The important thing to do is understand the needs that aren’t being met. After that, it won’t get in the way as much.”

That piece of insight changed the way I thought about the whole situation. Something was, very obviously, wrong — my need to be socially connected doing purposeful work was not being met at a time when I tried to take responsibility for risks nobody else would.

As I worked through similar situations with my therapist, both professionally and personally, I learned how to read my own internal reactions far more effectively than I had ever done before. It gave me a preemptive strategy for mediating my behaviour by first asking myself whether or not my reaction was to a given situation or something else, either related or otherwise. By addressing each emotion head on, I neither suppressed it nor gave in to it. I simply let it inform my thinking as another data point.

Understanding Others

Being better in control of my behaviour immediately improved my relationships, as others didn’t have to bear the burden of the emotional consequences they didn’t cause. The much more profound consequence of understanding myself, however, was learning to understand others better, too.

I can quickly guess what another person might be experiencing, based on what emotions they appear to be displaying. Based on that guess, I can test to see whether or not I am right. By doing so with kindness and genuine concern for the other, I learn more about those around me and forge more meaningful connections that build real trust with those I work with.

Why is this so important? If it isn’t already obvious, it’s about the opportunities that we encounter every day. Different people have different life goals and expectations. When we see an opportunity involving another person, oftentimes, it is in relation to our own aspirations, needs, and desires, not based on theirs. By having deeper, more authentic relationships, it’s much easier to find well-timed opportunities that better match the actual values and plans of those around you. I do this by looking for what I call the “common ground”.

While I was the CEO of a startup with very little resources, we needed an explanation of the key parts of the laws regarding our upcoming flagship product in order to best serve the marketplace. While we had eager clients contacting us daily, after calling a few lawyer’s offices, we soon realized we lacked the resources required to do a proper legal review.

We asked around for a recommendation, and eventually landed a meeting with a young lawyer through a common acquaintance. At the beginning of the meeting, I asked how he knew our acquaintance, and learned it was through a service club dedicated to young professionals. I further noticed that this lawyer’s behaviour, while outgoing, was approval seeking, suggesting that he was nervous, perhaps, or eager to land this work. After the meeting, I asked more specific questions regarding his career thus far, what he enjoyed working on, and some of his goals for the next few years.

I learned that he was hoping to build his practice, and was interested in emerging applications of law in the tech sector. Having already spoken with other lawyers who were less interested in tech companies, it became clear that our aspirations shared common ground. He was eager to take us on, even at a reduced price, because it afforded him the chance to do what he was really excited about. In the end, the work done was beyond our expectations and allowed the company to move forward as best as possible. We may well have missed out on key insights required to get the job done right had we gone with somebody else, and he was forwarded lots more interesting (and full-price) work from us because of the great job he did.


Discovering real opportunity begins with understanding the needs, desires, values, risk tolerances, and goals of ourselves and those around us. From collaborators to customers, when we can find the common ground, we find great opportunities. Learning to understand ourselves and others is the key to recognizing opportunities as they come to us, and therapy is a great way to work through common situations you already encounter with a psychological expert to gain the skills required.

This interactive guide can be completed in minutes and uses the best scientific literature and in-depth product knowledge to help you choose how to access therapy. It provides price information, and considers multiple important factors, highlighting how each popular option evaluated does or does not meet your criteria.

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