Enjoy the Journey

My old college roommate posted a few weeks ago that he was starting to read The Hitchhiker's Guide to the Galaxy to his son. His son asked what they were going to find out at the end of the story and my roommate answered, "We find the answer to life, the universe, and everything." On cue, the child asked for the answer, and if you're familiar with the book, you can probably guess my roommate's response and see the child's puzzled reaction. For those who have not read the book, the Cliff-Notes version is that the supercomputer Deep Thought spends 7.5 million years trying to find the answer to life, the universe, and everything. After such time, it is finally prepared to give the answer to two men. As Douglas Adams writes:

"All right," said Deep Thought. "The Answer to the Great Question..."

"Yes..!"

"Of Life, the Universe and Everything..." said Deep Thought.

"Yes...!"

"Is..." said Deep Thought, and paused.

"Yes...!"

"Is..."

"Yes...!!!...?"

"Forty-two," said Deep Thought, with infinite majesty and calm.

Oh, if only the answer to such questions could be reduced so.

I've been lucky to spend time with the next generation, the future movers and shakers and leaders. It is a true reverse mentorship. I share the nominal lessons that I've learned along the way and they keep me current on the latest trends, thinking, and technologies. It's very Gucci. (See, I've been listening.) They are some determined and hard working folks that have done very well for themselves already and are continuing to make the primary, secondary, and tertiary moves to advance their careers. I envy their energy and drive and the specificity of their future visions, mapped out like the itinerary of a seven-day-six-country vacation. Most are trying to get to "The Big Chair" which, in the in-house legal context, would be the general counsel or chief legal officer role. Age forty seems to be a common target date and they're busy constructing a portfolio of experiences and achievements to increase the odds of reaching that aim in time while continuing to measuring their performance against a personal index.

From my seat it's fascinating to watch them try so many different approaches. (I joke that I'm in the cheap seats, eating my popcorn, enjoying the action.) Some of them are already the legal heads of certain businesses, gaining a deep expertise in the ways of their clients; others are harvesting a broad range of experiences across different domains, moving every few years for new knowledge; a few are working hard on their management and people leading skills; one or two are trying to do all of the above, somehow at the same time. They're proving that there's no one path to career advancement. I don't know who will reach their goals first and I know not to play favorites. The best I can do is give them constructive and honest feedback should they ask me for it; otherwise I just sit back and listen.

And they're asking some great questions. What combination of experiences will they need to become a viable candidate? Which connections do they need to make and networks do they have to join today so that the right doors will open tomorrow? How do you develop the ever-fuzzy-you-know-it-when-you-see-it gravitas needed to get a seat at the executive table? They're plugging the knowledge and experiences gained into their formulas and chugging to the next opportunity. This, of course, is all very rational behavior. There are few openings at the top, especially if the top spots that you covet are at companies listed, say, on the S&P 500. Like the selectivity of top schools, the top jobs at the big companies often go to those who, over time, have connected the most relevant dots, raised their hands early and often for the best assignments, put themselves out there enough to build that all-too-critical muscle of putting yourself out there. I am reminded of a former colleague who said - and I had a hard telling whether he was being facetious - when the head spot on his team opened up, "I'd do it if they asked me." It doesn't work that way. Nobody gets "asked" for the top spot. You have to go out and get it.

Yet I worry a little. I worry when it appears that folks seem more focused on checking off the boxes, like completing the basic requirements needed for college admission, than taking the time to let their experiences sink in. When the mood is more of a "Ok, what's next on the list" than a sense of reflecting on what just happened. When the statements are something to the effect of, "Well, at this age I should be here. And I need to be there by then." I understand that it is all may be part of a plan and it's important to have a plan and to measure and make progress on the plan, but careers, life, the universe, and everything, can't just be all about the plan. As John Lennon once said, "Life happens while you're busy making other plans." Life has a way of interrupting and disrupting even the best laid ones and one critical skill to learn is the ability to make do with the unplanned evens that life foists upon you. (See e.g., 2020.) Sometimes, to change things up, I ask them less substantive questions and more general ones. Are you having fun yet? Do you like what your doing? And my favorite, what is it that do you really want to do? Then I become annoying and bug them to take their vacation and like a real vacation where they don't check e-mails. Oh, and I may tell them to lighten up from time to time.

Look, I get the hustle and haste. Paying off student loans and eventual financial security; having been at the top in everything they did and that being at the top matters; pride in achieving a long-term goal they've worked hard to get; seeing their peers reaching the highest levels: Motivation comes from all manner of sources. But I am reminded about that old saw about it being all about the journey and not the destination; that if you are so focused on one specific outcome, you may not see the other possibilities, allow enough space for serendipity. I have some good friends who still talk about an unplanned side trip to a town in Germany and how they stumbled upon a meal of a lifetime and a night at a lovely hotel some twenty years ago. It was the unexpectedness and spontaneity, that seemed to have left such an impression on my friends after all this time. Analogously, the same might said about career paths and the detours and the unexpected surprises that you might find along the way if you're not closed off to them. How if you're laser focused one one outcome, on one place to go, then you may miss the other unexpected side-trips that might come your way, opportunities that don't appear on the map because they weren't on the expected path. There are jobs big and small, titles fancy and not so fancy, businesses established and start-up; If you have one thing in mind, you might not be so open to the other things that you wouldn't so much mind.

If asked my philosophy, it would be simply this: Savor life, don't press too hard, don't worry too much. Or as the old-timers say, "Enjoy." -- Jerry Weintraub

I guess in the end I hope they will take the opportunity to savor their career experiences. Not to worry so much whether the experiences that they have are the right ones they need for some prospective future and if their experiences are adding up the way they need them to add up. To focus more on enjoying the experiences that they're having right now. To stop wondering so much as to whether they're still on the right timeline and to have more wonder about the time they are having. Maybe to quit stressing so much about whether they're getting the very best answers and to try more to seek the important questions. Questions of their friends. Of their families. Of themselves. (Questions are more interesting the answers anyways.)` It takes time to figure out careers and life and the universe and everything. You have to be a little patient. Okay, a lot patient. To let the experiences sink it. Gestate. Marinate. And by then you'll have more experiences which means that you'll have to let even more experiences sink in. Gestate. Marinate. It's a virtuous circle. Or a circle of hell. Depends on how you look at it.

And the answer to those questions at the end of the day is probably not 42. But who knows, maybe it will be.

Please note that the opinions expressed herein are mine and mine alone and do not represent the opinions of and are definitely not endorsed by my employer Raymond James. Thanks!