This week I want to do something a bit different from my usual articles. I want to give you a peek into part of my own journey, in the hope that it may help you with yours. I want to talk to you about my experience in dealing with ambiguity.

You must learn to deal with ambiguity to protect your energy. Ambiguity - especially if you are an entrepreneur - causes anxiety and self-doubt as a result of outcomes that are external to us (i.e. we cannot control them). We know that we can’t control everything, even though we ultimately must manage the outcome of whatever happens.

In many cases, we are bothered more by not knowing how things will turn out than we are of dealing with the consequences we may face.

Read that again; it is a lesson hard-learned from years of working with highly motivated individuals like you.

Wisdom

The first day of orientation for my second Ph.D. program, we heard a brief talk from the most senior professor on the faculty. Wise and white-haired, he was the Dumbledore of the faculty, respected and revered.

His was a cautionary tale, a warning about the difficulty of the famously difficult doctorate in clinical psychology (one of my classmates already had her MD degree; she later said it was nothing compared to the first year of this program). To my surprise, he did not speak of the huge reading load or the four semesters of advanced statistics or the scores of psychological tests we would have to administer and document, or even the hours of “pre-doc” internship we would endure.

Unlike most Ph.D. programs, clinical psych students have to complete more than a thousand hours of internship. Unlike most professional programs, they are expected to complete and defend a dissertation. Literally the most difficult of both worlds.

But these formidable challenges were not among his admonitions. The thing that caused the most trouble for clinical psychology doctoral students, he said, was ambiguity.

Because there are no guarantees, no sure outcomes at this level of behavioral science. There is no Avogadro’s Number, no Ohm’s Law that will yield exact results. Like life, he explained, we would have to become comfortable with the “not knowing” that is a part of the human condition. And this immutable uncertainty was a frequent barrier for students who previously could always calculate the “right answer.”

His words proved to be prophetic not only for work with clients and patients, but for the challenges of the entrepreneurial journey I chose to pursue.

Being OK

To deal with ambiguity, you have to learn to be OK with not knowing.

You see, I am something of an expert in ambiguity. I have never taken the safe, “tried-and-true” path through life. I couldn’t handle the boredom that comes with that much predictability.

I want freedom. I want the challenge of deciding my own path and the unmatchable satisfaction of overcoming the obstacles that may arise on the way. I never wanted the “20-years-and-retire-with-a pension” corporate life. It was more important for me to pursue my life as I saw fit than to be a slave to my 401(k).

I learned what I need to learn for the first part of my professional life, working in successful corporations to see how they operated. I started businesses in one of the most competitive cities in the world, without a business degree or a pile of money. I partnered with multimillionaires in a notorious “shark tank” and convinced them to invest in me and my ideas.

I built a college, a wellness center, a renowned music venue, a recording studio and more, all from my own imagination and grit. I made tens of millions of dollars and traveled the world along the way.

And yes, I did great with the ambiguity of grad school in human behavior, a couple of times.

I won huge and failed big and always landed on my feet. But I never gave into the mundane, the boring and predictable. That doesn’t mean I’m reckless; quite the opposite, actually. In fact, I tend to be very conservative. I carefully over-research and under-promise and over-deliver.

I learned to be a great manager and leader (they are radically different skill- and mindsets). I learned what I needed to know about corporate finance and lawyers and audits and CPAs and accounting and human resource management and all the rest. Because that’s what it took for me to meet the challenges of an extremely fluid and ambiguous path.

The important thing is to have the knowledge and skills to bounce back, no matter the outcome.

Let me pass on what I learned along the way.

Know Thyself

The most important component to deal with ambiguity is faith in yourself that you will overcome challenges as you meet them. It has less to do with knowing the outcome of a given action, and more to do with faith in your experience, that you have made the best decision you could with the information available to you.

It may take some time to develop the knowledge and skills that underpin such faith, but that’s the price you pay for competency.

The second most important thing is to have a source of strength when things get scary. I had - and have - my purpose “top of mind,” as they say, which is formidable because it makes my “why” much larger than my personal satisfaction or finances.

I learned how to hold my own with the family of presidential candidates, and successfully negotiate with multimillionaire venture capital investors and businessmen, and keep the lawyers of federal, state and local regulatory agencies at bay. I am confident you can develop the same abilities and have the same results.

The third thing you need to deal successfully with ambiguity is commitment - the ability to stay the course, even in the face of uncertainty.

There will always be people and situations that seem to be overwhelming. There will always be fear that “something could go terribly wrong.” There is always the feeling that maybe we should just retreat to a place of safety and hope it all goes away.

But it never does. That is the secret to life: there are no guarantees. You must manifest your own future.

Ambiguity

You can gain all three components to enable you to get whatever you desire out of your life. Without hiding behind someone else’s success. Without sacrificing your freedom. Without trading your happiness for security.

The satisfaction and happiness and rewards that you find on the other side of ambiguity - of fear - are more than you can imagine in your wildest dreams. Stay the course and don’t be swayed by the “what ifs” of the future.

The answer is to learn as much as you can, then plan for - and do - the best you can to work towards your purpose and protect your well-being.

And learn to let go of the rest.



To learn more about how to use these concepts or to inquire about working with me, you can contact me on the Hardcore Happiness website, the comments section on my Substack or Medium accounts or The Authentic Life Blog page. If you have found value in this article, follow my Instagram account for daily insights, or my X account for occasional tweets. To support this community, you can Buy Me A Coffee or donate through my Patreon account.

- JWW