What do you do when what you do for a living no longer gives you pleasure? In fact, you hate coming to work and you are up to here with the whole thing — but you are the owner.

This puzzle has brought two of my clients to their knees and into my arms. In the first case, “Bob” has a wonderful niche in the real estate industry and makes a lot of money. But he is burned out, afraid of the looming recession, overwhelmed with details and generally miserable. We worked on the various issues and decided that the solution was to hire someone who could run the business, so that the owner could do something else. The owner also recognized that he would have less personal income. The outcome was fascinating.

We interviewed and found a huge talent. The new talent is bringing in more business and has won the respect of the entire team. The irony is that Bob now wants to come back to work — he loves being at the office. The jury is out, but the fact that when Bob did not feel that he had to be there, that the ship would not sink if he were not at the wheel, then he was free to see his business in a new light. His reduced personal income (trust me, he is not going to miss a meal) is worth it for the freedom.

The dark sentence here is that most “owners” see themselves as indispensable (think Musk, Zuckerberg et al.) and in fact, letting go sometimes is not only liberating for the owner, but more importantly for the company as well.

Next up is “Sam.” This one is more problematic. It is true that Sam is the owner of his business, and he is the best employee, he does the work better, faster and more efficiently than any of his other workers. The business is profitable, but if he doesn’t work there, he doesn’t make enough money for him and his family. In his case, not working will affect his personal lifestyle, which at this point is stable, happily married, kids and no debt.

There are a large number of people in Sam’s dilemma. He lives on what he makes, and he feels both pride and guilt that he has created jobs for other people in the company and they would be adversely impacted if he were to leave.

The agreed solution for now is a sabbatical for two months. He will go to the office one day a week, no more. I am not sure how this will end. But the macro view of these two stories is that all of us have to make trade-offs.

We are all constrained by money, family, relationships – and I would suggest that for most of us, at some time in the working cycle, we feel burned out, fed up, dismayed, bored and angry (there are another 23 adjectives, but you get the point). How we deal with these feelings is critical to our well being.

I believe that the world turns on behavioral economics. How do we make rational decisions — and rational by what measure? How do our emotions inform those decisions? We need to consider the possible black swans, as well as the potential unintended consequences. Some decisions are permanent, and some are available for a do-over. Knowing which is which is critical. The “I should have gone to medical school” moment at some point is no longer an option. Think carefully about whom you marry. (We all think we do, but over 50 percent of first marriages end in divorce.) You would think someone would build an app to solve that puzzle.

And finally, let’s give a shoutout to the aging entrepreneur (over 60) and the dilemma of retirement. How do I let go of what I did, which defined me for more than 30 years, and without it, I will be lost, alone, depressed, suicidal (you get the idea). Statistics say that leaving your job and retiring makes you happy for a while, but literally after a few months, there are the unsettled “Who am I?” issues. Do I go on a cruise around the world with other old fogies or find a nonprofit that needs me. Can I redefine my life?

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