Mile-Markers of My Entrepreneurial Journey

By Kevin Choquette, an EO San Diego member, and president and founder of Fident Capital

If you want to achieve, become a world-class learner. That’s the tweet-sized heart of this blog post. I grew up in a loving home of modest means, and creating a future became a mandate. I don’t chase after success just for the money. My father instilled in me the “work hard” approach to life, and I’ve employed it to address basically all challenges associated with this pursuit.

That ethic has been both a blessing and a curse. Rewards certainly come from the “Git ‘er done!” mandate and the immediate, tangible results of a hard day’s work. But humility comes in seeing how slow my progress has been, precisely because I’ve addressed most challenges with the same strategy: work harder.

I’m very curious about the world, which has super-charged my work and catalyzed an odyssey that transcended 26 jobs, several industries, and fields of study as contradictory as music and business. Being inquisitive has been an enormous asset, as I have developed a unique and rich understanding of varying areas.

But work and curiosity don’t appear to be the total answer. After more than a dozen years in commercial real estate finance and a reasonably high degree of proficiency, my business doesn’t always make the progress I desire. I strive and that allows me to progress toward the target, but sometimes I just work, and work, and work. Think “Groundhog’s Day” or “The Truman Show.” I wake up, do exactly what I did yesterday and expect a different result. What’s missing?

I’m not the only entrepreneur in this boat. For me, the view from the boat looks like this:

  • Take the initiative and accept responsibility for the outcome
  • Work hard and remain curious
  • Think “working even harder” will break challenges/ceiling
  • Find that challenges/ceilings remain in place

Only through deeply personal and robust learning can we truly make “don’t work harder, work smarter” a reality. Curiosity is good, but more weighty learning is required to change deeply held beliefs so that we can see the world differently. It is the change in who we are or how we think that distinguishes this kind of learning and makes it valuable.

After working with an executive coach and reading “Fierce Conversations” by Susan Scott, I saw that by not having difficult conversations with those closest to me, I was doing both of us a disservice. Scott holds that “the conversation is the relationship.” I screwed up the courage to have my first “fierce conversation” and had such an incredible result that my view of conflict shifted completely. The conflict avoidance in my nature is still present, but I now feel the joy of dialogue and respond to conflict by leaning into it.

I joined the Entrepreneur’s Organization about four years ago, which employs a “Gestalt” method for examining challenges. In a confidential setting, people share without risk of judgment and garner direct feedback on the issue. Years back, I presented to the group how a myriad of business choices left me feeling confused. After a long series of low-ego, honest, experience-shares, I saw I was using confusion as a crutch to avoid making hard decisions. Now, I can see how my behavior may hold me back and consciously choose to move forward.

For help with strategy, I turned to Dave Crenshaw, a great business coach in Salt Lake City. He refused to even meet until I applied his time management system which forces everything in your life into the great common denominator– time. When I tried to cram my tasks, meetings, calls, workouts, etc., on a calendar, it was painfully obvious that I was bankrupt on time. Now, I say “no” to more, and focus on aligning my current efforts with long-term goals.

Each of these lessons proved among the mile-markers along my journey. While goals like more income, more free time, more employees, better profit margins, better investment results, etc., are things to measure, they don’t impact the power of learning events and tools that facilitate approaching a problem in a new way. What’s next?

The present and my tendency to simply get it done, whatever it may be, holds me back. Ironically, the positive of these impediments are material contributors to what got me here! I’ve found a few approaches that seem to accelerate or catalyze opportunities to grow:

  1. Get a coach. Insights come from having baggage reflected back at me, and for the value of accountability. I also want to leverage off the coach’s experience influencing many others in similar situations.
  2. Seek engaged and turned on people. The best way to predict your income is by looking at the five people closest to you. The money part of that is a reflection of the impact of powerful, vibrant, and shared dialogue, thinking and insights. The learning can come while out for a surf, after three beers, a quick phone call, or as the result of a week or months-long dialogue.
  3. Accept vulnerability. My challenges are not something I need to own. The baggage is mine, but taking it off and pointing it out allows for detachment and understanding of new vantage points. Others’ vulnerabilities allow me to see how they, too, have hang ups, just as I do.
  4. Embrace systems and measures. Measurement is my weakness, but driving awareness by employing objective and regularly recurring measurement is a fantastic tool. I send daily emails to myself asking things like: “How well did I focus my efforts on building the business vs. doing the job? Rate it 1 to 10.”
  5. Heed emotional experience. Our deepest learning comes from experiences, not facts. Wisdom is imprinted upon our soul and changes who we are when emotion brands it upon us. Tony Robbins and others make experience (not lecture) a key underpinning of their teaching method. Someone steals an employee, you feel it, you learn. You make a tax blunder, it hurts, you learn. Someone cheats you, you learn.

World-class learning allows us to change our beliefs, behaviors, and vantage points so we can employ internal or external resources to achieve our goals. Our inequality is undeniably driven by our ability to learn, and the ability to learn is probably the single greatest equalizer that exists.

If you’re not getting all you hoped for from the gift of life, perhaps learning can be a place to focus your just-work-harder energies.

Categories: Best Practices Entrepreneurial Journey


One Response to “ Mile-Markers of My Entrepreneurial Journey ”

  1. Eugene Thompson on

    Great piece, I see some of the same hurdles in myself and my business approach. Thanks for sharing. Dave Crenshaw has been my coach since the first of the year and time management has been an amazing insight in where I had failed previously.


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