I’m 55 and just sold my company. Should I go back to college and earn my degree?

“I am a 55 year old guy that sold his software company to a public company last year.  I have no college degree but have always felt I was missing something.  I have tons of real world business knowledge.  I don’t want hitting a little white ball to be my future.  I want to share my experiences and obtain a degree.

Thoughts?”

–Carl

The Harvard MBA says:

Carl, you have what we like to call a “high-quality problem.”  Most people would love to be wrestling with the challenges of financial success and independence.  But a high-quality problem is still a problem.

Indeed, a number of my friends have made a lot of money either via IPO or sale, and struggled to figure out what to do next.  If you’ve spent your entire career striving to achieve “success,” what do you do once you achieve it?

One friend tried retiring at the age of 52 after leading his startup to a successful IPO and running a publicly traded company for a number of years.  He even devoted a significant amount of time to golf lessons!  (I suspect that golf has three major attractions for the wealthy: It’s a fun activity with breathtaking views, it takes up an inordinate amount of time, and it reduces the chance that you’ll run into poor people who will ask you for money.  The ridiculous outfits are just a bonus.)

He found retirement boring, and came out of retirement to found another company.  After selling that company, he does appear to have retired, but this time, he had a secret weapon: Grandchildren.

It sounds like you’re pretty self-aware and that you feel like college may help you find what you think you’ve been missing. On the other hand, it also sounds like you feel some trepidation at going back to school at age 55.

It strikes me that you’re hoping that going back to college will do several things: 1) Allow you to share your experience with young people who will benefit from them, 2) Give you a chance to explore interests and activities long deferred, and 3) Let you earn a college degree.

From a practical standpoint, earning a college degree strikes me as the least important of those goals, though if you discover along the way that you want to pursue a path that requires such a degree (such as obtaining an advanced degree so you can teach), that might change.

Also, there is a great deal of work involved in pursuing full-time studies, ranging from the prosaic (getting your old high school transcripts together) to the unpleasant (taking the SAT) to the absurd (asking people for recommendation letters).  It’s enough work that it might take you some time to get started.

Finally, I’m not certain that 18-year-old freshmen are the ideal folks with who to share your experiences.  They may be more interested in consuming alcohol and pursuing members of the opposite (or same) sex than in hearing about your wealth of business experiences.

Rather than jumping to full-time studies right away, might I suggest tackling your objectives directly?

If you want to share your experiences with young people, seek out the local entrepreneurial community.  These folks will be delighted to hear from a successful software entrepreneur.  If you want to guarantee your popularity, simply hang out your shingle as an angel investor.  Trust me, there will be many people eager to hear your stories!

If you want to explore interests and activities long deferred, jump right in with courses, either through your local college/university, or via clubs and other organizations.  In fact, this might be even more effective than enrolling in a college degree program, since you won’t be stuck taking required courses for a year or two.

If after taking these two steps, you discover that you do want to pursue a degree, you’ll have plenty of new experiences to help you feel confident in your choice.

Do write back and tell us what you decide to do!

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