Quit Accenture, Move to Nantucket…and other decisions you won’t regret when you’re 40

No decision is truly risky if it aligns with who you are and what you want.

I was 23 years old when I first heard these words from my former mentor: Aspen Skiing Company CEO, Pat O’Donnell.  In the late 1980s, Pat went from being President of the National Wildlife Defense Fund, a large US non-profit, to become CEO of Patagonia, a large, for-profit, outdoor sportswear company.  Discussing the experience with me, he spoke candidly that the decision to make the move was “terrifying.”  “But,” he said, “no decision is truly risky if it aligns with who you are and what you want… the only safety net you have is your values.”

As I watch some of our most revered institutions – our banks, our retailers, our technology companies – flail or flounder today, the advice seems more prescient then ever. A company can’t give you the certainty or peace of mind it once might have; today your security has to come from within.

Below, I’ve captured 20 thoughtful ideas and advice on decision-making in your 20s; sent to me by over 40 thoughtful, high-potential 30-somethings; people who have made their decisions and lived to tell about them.

Before I share those perspectives, though – let me first offer my two-cents:

1. If you don’t know what you want, you’ll never get there.  I had a friend in college – a star on the woman’s soccer team – who started getting up everyday at 6am to train (not unusual today, but a time that few college students knew existed!). Why?  She was preparing – training her body, mentally and physically – for a big game she was to play in London the following week.  The start time? 11am Greenwich Mean Time (London) – the equivalent of 6am Eastern Standard Time.  Impressed?  So was I…  I use this story as a example of how the best align what they want – in her case, to perform at her highest level despite the logistical challenges – and what they do.

Too few smart 20-somethings really know what they want.  They know what they should want…a good job, health insurance, a girlfriend, fiancé, small apartment, baby… But very few know what they would want – if they allowed themselves to want anything in the world, sans restriction.  How do you get what you want if you don’t know what that is?  Now is the time to figure this out – while you don’t have a wife, husband, baby or graduate school debt.  The longer you wait the more difficult that conversation becomes.

2. Create space for your decision-making.  There is no “space” (e.g. unscheduled time for reflection) in the life of today’s 20-something graduate of elite education.  You received your offer from PIMCO or PWC or P&G before you even graduated from college.  After a summer orientation, workload began to build and the time in the office grew.  Despite promotion after promotion, life didn’t slow down – in fact, for most, it sped up.  Finally, you start applying to graduate schools.  Not because you are convinced that Tuck or Wharton or Ross will get you a step closer to your life dream, but simply because you need a break from the corporate grind.

The CEO of a large international aerospace company recently shared with me that it wasn’t until he was 38, at the London School of Economics, that he ever had a chance to stop and ponder why he had made the decisions he had.  That’s not OK.  Newton’s law of inertia: what is set in motion tends to stay in motion. Once you get too far down the “traditional” path, it will be hard to pivot.  Not impossible, but much harder than it is at 25.

Create space for yourself.  Carve time out of your schedule everyday to reflect on who you are, what you are learning and how it all maps back to the greater purpose of your life.  The more clarity you have around who you are and what you want, the easier your decision-making will be.

Advice from Smart 30-Somethings | On Decision-Making in Your 20s…

1.         Take your chances now; risks become much harder to take later on in life. Quitting a consulting gig with Accenture when I was 30 years old and going to Nantucket was difficult, but worth it. In your 20’s you can and should take risks

2.         When you find yourself in a hole (e.g. career, relationship, where you live, whatever), stop digging.  Looking back you realize how short, and valuable that time is during your 20’s and if you “waste” it you can put yourself at a big disadvantage.

3.         Entrepreneurial “failure” isn’t perceived as such by many business professionals. A “failed” endeavor led me to Buenos Aires, Argentina; following my passion for Argentine culture.  There I got my “ya yas” out, and eventually arrived professionally. I now work with Latin America on a daily basis.

4.         Life is about tradeoffs. Trade wisely; search for win-win outcomes.

5.         I was laid off from a Financial Services job when I was 24… I worried about being laid off for a year and when it happened, I thought my world had ended… It turned out to be the absolute best thing that happened to me in my 20s.  It set me free from a life that I hated; a life that I had chosen for the wrong reasons. Everything worked out.  Opportunity and growth comes from overcoming hardship, not worrying about it.

6.         We are lucky in this country to have a flexible social class structure and well-developed respect for individuality such that each of us can try our hand at something “unconventional,” and not risk some kind of permanent dislocation from the order of things. We can still end up successful, with a spouse, a family and a well-integrated life (if that’s what we want).

7.         While there is a point where changing career paths is challenging – that point is not 22, or 25, or even 28. Keeping this in mind will free at least some people to try things and go places that they otherwise would avoid as too “risky” or as having “no future.”

8.         I wish I had gone somewhere great for a year after college (mountains, beach, international).  Now, with perspective, I can see that experience, and the personality it helps to develop, is so important. There are so many paths in life and the most interesting ones seem to reward those who are really brave and operate off the beaten path.

9.         It is old advice, but you never regret trying something and failing, you only regret what you didn’t do.

10.      No mistake I’ve ever made has been the end of the world, nor did any mistake ever really deserve the amount of worry and stress that went into making the decision or change in the first place!  I’d have been better off just choosing a path and going, as opposed to deliberating about stuff much at all.  I’d have had way fewer ulcers in life

11.      Expect the unexpected.  Don’t rule yourself out of something because you think you know the outcomeNothing is ever assured.  Statistics are statistics for a reason, there is ALWAYS some chance for a different outcome.  Both personally and professionally! I learned this the good way…an open mind resulted in an incredible marriage and a second baby on the way

12.      Tough decisions take courage; find it.  Decision-making can be daunting at times; but focus on doing what is right for the situation at hand—then learning from your decisions.

13.      An Osama bin Laden-type a*shole can take your life at any given point. You might as well live happily.

14.      Opportunity can sometimes knock softly.  Be listening for it. Saying “yes” to both big and small opportunities will help you to develop a better sense of who you are and what you really want.  It will also lead to the great life/career opportunities. An example, when volunteering out of college, a co-volunteer was talking about a project they needed help with at the company he works for. I volunteered to help, which lead to helping with other projects at the company, which lead to part-time work, which lead to full-time work, which lead to a 10-year career and a consulting business in the industry.

15.      Don’t just follow the money. In your 20s you have the ability to take risk that might not be afforded to you as you get older and build a family.  As a result, you should try to find an activity/job that truly fascinates you; this will lead to more fulfillment in the long run

16.      Sometimes, you just need to get off the beaten path for a year or two.  Do it. You’ll never get your 20’s back.

17.      If you work hard, you will be afforded many incredible opportunities; saying no to one isn’t the end of the world.  Be brave enough to say no to the ones that are not truly aligned with what you want to do.  

18.      Set a life vision, then prepare to be lucky. The joy of each day should be the struggle…if you love what you’re doing, the challenges will be fun to tackle. You’ll look at problems with relish.

19.      There is a saying in basketball that is very much tongue-in-cheek but nevertheless viewed as containing a kernel of truth: I never made a shot I didn’t take. Interestingly, somebody took a look at both scenarios: what happened to FG% as a function of consecutive shots made (or missed). The finding was maybe not surprisingly: statistically speaking, the best time for you to shoot is when you’ve missed your last few. The worst time for you to shoot is when you’ve made your last few. This is a bit different than the old truism “things are never as bad (or good) as they seem”. The way I’d say it: Things may indeed really be that bad (or that good), but that doesn’t mean they’ll stay that way – in fact it’s practically guaranteed they won’t. Besides being cheering in hard times and humbling in good ones, it may focus the mind on the most important question: what do I do NOW?

20.      To quote Joseph Campbell, the best way to save the world is to be alive within yourself.

Commercial plug: Most people need a thought partner on this stuff. At the very least, someone to double-check their calculus.  It’s not hard, but it’s not intuitive.  Email me and we’ll set up a free Life Strategy Reviewwe’ll figure out how to get you from here to happiness, faster.  


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