Career Doubts and Regrets: Here’s How to Eliminate Them

Thursday, May 2, 2019

Delray Beach, FL.- A friend and former protégé, who went off to start his own very successful business, wrote me a while back. He said:

Today I find myself wealthier than ever before. And I suppose freer than ever… yet I find myself terribly unfulfilled. As I look back on these last seven years, I’ve learned and grown a great deal. Yet sometimes I feel I squandered prime years of my life in exchange. 

 I used to do daring things, unique things, (mildly) impressive things. Now I feel mired in a milquetoast existence that slowly rusts my soul away.

 I feel rather like old Ulysses in Tennyson’s poem. Who knew I would be feeling this way at 40 instead of 80.

Then he asked:

When looking back, was there ever a major decision that you wish you would have made differently?

And here’s what I said:

I’m sorry I haven’t gotten back to you on this. I wanted to turn it into an essay, but I did three drafts and didn’t like any of them. So I’m going to make this short and sweet.

I think the question behind the question is whether I think it’s possible to have your cake and eat it too.

Based on my experience, the answer is yes.

When we’re young, we have exciting dreams about the future that affect us deeply. As we settle into relatively mundane careers, we can ignore our youthful fantasies and even forget them. But they are based on strongly held values that eventually come back to haunt us. In your case, it was the desire to be an adventurer. For me, I always wanted to be a writer and a teacher and a Renaissance man. And even though it turned out that the driving force of my adult life was all about making money, I was able to scratch those idealistic itches.

I never gave up my day job, but I did find ways to become a writer (by starting ETR and then using it to write many books) and by using that to teach people what I knew about business and wealth building. I also managed to scrape out time to learn three languages and make three movies and climb Mount Kilimanjaro and stay married and father three children and collect art and develop a real estate portfolio, etc.

I did almost all of those things after I turned 40.

So that’s one answer…

The other answer is that I have, over many years, developed an attitude that is a mix of Stoicism and Existentialism. I believe that I have the freedom to choose my fate. More importantly, I believe that although I had a deep desire to be a writer, teacher, and Renaissance man, those pursuits in themselves had no value except the value I willed to them. Recognizing that they had no intrinsic value was very liberating. It allowed me to forgive myself for falling short on achieving them. (For example, I’ll probably never teach at Harvard.) It also allowed me to willfully value the work I have done as a businessman. And once I began to do that, I was able to truly enjoy and feel fulfilled by it.

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