Topics: Dream Job · Fulfillment · All topics
Andrew Wcity withheld

I am 32 years old with no degree and have been considering going back to school for an M.B.A. I have a great job and a great house in an awesome resort town on Lake Michigan. I work in a bar and the lifestyle is starting to take its toll on me. I love my boss so much that the idea of leaving him to pursue another career crushes me. I have the resources to buy into the bar but he doesn't seem to want me to for fear that in order for his business to be successful, he needs a partner with deeper pockets. I have what I estimate to be a once-in-a-lifetime opportunity to run a computer-networking company that I recently founded with an incredibly talented partner. We have discovered a technology that no one really understands yet and I'm afraid that my inability to run a business will render the whole thing and my life a scrap heap.

Daniel's advice

Nothing like starting off a new year at a crossroads! In one short paragraph you’ve listed at least three different paths open to you that could shape your career and future.

On first glance, it would seem you are wondering if Option A (we call that the back to school and then on for an advanced degree option), or Option B (we call that the staying where I am because I love and adore my boss with the possibility of buying into the business option) or Option C (we call that the starting a new business with possibly ground breaking technology as the outcome option) is the way to go. We’ll address those options but think a deeper issue is really what’s at the bottom of your quandary.

But to get started, let’s take each option at face value.

Option A means returning to school to pursue a degree (and perhaps an advanced MBA degree). If you choose this route, you will be looking at a rather long stint in school and a depletion of your current resources, but you will gain an education that will help you, not only in the marketplace, but also by becoming a more educated and (usually) more interesting person with a commitment to personal growth. What you don’t say is what it means to you to get a degree and an MBA. In the best of all possible worlds, when you finish your education you will find a job that offers you money, meaning and fulfillment. In the worst case, you will find that you’ve spent your time, energy and resources pursuing something that you thought would open doors but didn’t.

Option B means you stay and work with someone you respect and admire and who presence probably makes up, in large measure, for other things you don’t find at this job and for the “lifestyle that is beginning to take it’s toll� that goes with working in a bar. Even though your boss wants someone with deeper pockets as a partner, if that someone doesn’t happen to come along you might still have a chance for the buy-in (unless there isn’t complete honesty in his reason to you). What you don’t say is if you would still want to buy-in to this situation were this particular boss to leave for another opportunity. In the best of all possible worlds, you could become his financial partner and continue to work with him (don’t underestimate the value of having a boss you love – it’s priceless) and perhaps the added benefits and challenges of being an owner (rather than just employee) would bring you enough satisfaction to make this a viable career. In the worse case, you don’t get to buy in and then stay only until you can’t take the lifestyle anymore or this boss leaves.

Option C means you work in a new business with your talented partner on a ground breaking technology, but without the surety that you’d be good at running a company (in fact from your words it’s clear you feel substantial fear that you wouldn’t be good at this and would ruin the whole opportunity — is that fear grounded in self-knowledge or are you just unproven in this area?). This “once-in-a-lifetime� chance could prove to be so amazing in it’s potential that it doesn’t seem real yet, but also, as with most new businesses, has the potential for huge missteps and failure at every turn. What you don’t say is what exactly you would bring to the mix and what your job responsibilities would be. In the best of all possible worlds, this could be your ticket to the big time and offer you the chance to bring this new technology to the public and make a difference in the lives of many. In the worst case, you might try it and find that you aren’t up to the task and make a mess of the business and by extension, your life.

So, there you have it- a quick look at each option. However, the real issue we think you’d be better off dealing with is not “what do I do next�, but “what do I want to do with my life?� We know it’s a colossal-sized question with huge ramifications, but if you don’t deal with it in some fashion, we think it will be hard for you to decide which of these above options (if any) is what you want most to do next. You need to think carefully about what holds meaning for your life and for your career. Spend some time thinking, writing down and giving voice to what’s important. Ask friends who know you well to describe what they see for you (it’s always a mystery how our friends see us so differently than we see ourselves!) Do some goal and value exercises if that will help (there are oodles of books and internet sites on these topics). Write down every significant accomplishment in your life and see what made it significant. Watch for patterns and re-occurring themes — these will help you see what you have valued in the past.

You can get away with not doing the above, but it will be harder to make meaningful choices and prioritize what gives you the kind of mission and purpose that will allow you to be the best person you can be. If you give this short shrift now, you’ll probably find yourself at this kind of crossroads again and again, always wondering which road to take (which usually means inertia wins and you won’t do much of anything differently). That’s okay, if you want to be a person “who just lets life happen to them� and takes the road in front of them for as long as it’s interesting. Lots of people do that and they might argue that their lives are more fun, interesting, spontaneous and exciting! However, based on the fact that you’ve written into this discussion board and that you understand the depth and breath of the options facing you, we’re betting you aren’t one of those people deep down and that some introspection now on the “larger issue� of your goals, values objectives and aspirations will help you with this decision and future ones as well.