If you can check off all those boxes in your sleep, with no remotely serious second thoughts, congratulations to you. (You may also stop reading now.) On the other hand.

You may be among those (the majority?) who don’t honestly know what matters most to you in work. You may have followed a path of achievement largely prescribed and defined in others’ terms and not those of your own devising. You may be where you are largely because, at each fork in the road, you chose the course that would “keep more of your options open.” You may simply be where you are as a result of luck (hey, it happens!).

While this may be understandable, it simply will not do.

If you’re starting from a position of relative ignorance about what really matters most to you, my recommendation is to create some hypotheses and test-drive them. Do you care more about being on the front lines or in management? Do you work best surrounded by colleagues and in the thick of teamwork or more or less by yourself? Understanding that you are in a demanding profession and there is no substitute for putting in hard work, are flexible hours, somewhat within your control, important to you or is a regular schedule more your style? Caveat: Don’t form your hypotheses by, as they say, “fighting the last war.” If the last partner you worked with or client you worked for was a control freak, don’t assume solving that problem will take care of everything else as well.

Lawyers like checklists and roadmaps, and the article actually provides some, so I’ll leave you with a few.

  • Write down what the critical elements of a meaningful career would look like to you.
  • Enlist the help of a small circle of friends—family members may actually not be optimal for this purpose—to act as your private “advisory board” to help you on your path.
  • If you can experiment within your current job, do it. If you can’t, talk to people whose careers seem enticing to you.
  • Do not worry about your very next job; this is a long-term project. Focus on the long term.
  • Do not assume it’s too late to change. Certainly in America, it never actually is.
  • Finally, and this is probably most important of all to many who have led relatively unexamined lives so far: Don’t let your financial obligations get out of control, to the point where they own you lock, stock, and barrel. Give yourself some slack. Do you really need?
    • The second home?
    • The vacation in _________ in summer and ________ in winter?
    • A new car for you and your spouse ever year? Every other year? Every three years?
    • The largest and loveliest first home that realtors tell you you can afford?

If you think I’m kidding about this final list, I kid you not. It’s not whether you take a cab or ride the subway, eat out once a month or once a week, that will kill you. It’s whether the monthly “nut” you need to maintain positive cashflow constitutes a set of leg irons. Sherman McCoy, the famous protagonist of Tom Wolfe’s legendary Bonfire of the Vanities, a Wall Street “Master of the Universe,” with his Park Avenue apartment with hand-carved crown moldings, Hamptons home, his and hers Mercedes, bespoke suits, vacations in the south of France, and all of it, had nightmares of money “hemorrhaging—just hemorrhaging” out the door.

Don’t be Sherman McCoy.


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