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What I Wish I’d Known About Life, Love and Success In My 20s

By April 14, 2012 No Comments
By Ben Sands – Get free additional insights, tools, and leadership resources, click here

I was 23 years old when I first heard these words from my mentor, then-Aspen Skiing Company CEO, Pat O’Donnell:

“No decision is truly risky if it aligns with your values.” 

And I believed him.

His life was a testament to that truth.

Pat OD 2In his mid-20s Pat left a comfortable engineering job to move to Yosemite National Park. The reason? He loved (more accurately, lived) to rock climb. For the next couple of years this guy with a masters degree in engineering flipped burgers and pumped gas, among other things, in order to be close to the mountains and rock that he loved.

That decision – to leave a comfortable career path and follow his love – was the start of a storied career.

He would go on to run a environmental non-profit, build the Kirkwood ski area in California, and the Keystone Resort in Colorado and serve as the CEO of Patagonia, the global outdoor sportswear and equipment company, among many other professional achievements.

I ended up in his office because I had read this incredible life story in an issue of Ski Magazine – and I wanted to know how he did it.

When I asked him how he weighed the risks, and reward, of the many big decisions he had made in his life, he laughed!

“I was terrified,” he said. “But,” he continued, “I knew I was acting in line with my values…that was my safety net.


That advice couldn’t have been more timely.

I had just spent a full season living and working in the Colorado mountains and I was getting a lot of pressure to move back to the East Coast and “get a real job.” I didn’t want to…but was starting to question myself and and my dream to create an “extraordinary” life.

What I came to realize however, after speaking with Pat and others, is that the only mistake I could make would be to give up on that dream. To start doing what others wanted me to do instead of acting in accordance with my values, my beliefs, my vision for the life I wanted to live.

Thanks to that piece of advice, my life has never been the same.


I went on to make plenty of other mistakes in my 20s – a time period that psychologists now call “the defining decade” – but, all in all, things worked out damn well.

In the off-chance that you are in need of a little perspective and or advice, here are a few ideas to get you going.

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!).


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 really 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. You need “space” to make great decisions. Create it.

There is no “space” (e.g. unscheduled time for reflection) in the life of today’s 20-something graduate of elite education.

Say you received your offer from Google or Goldman or Gates (Foundation) before you even graduated from college…  After a summer orientation, your 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 automotive 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 Life, Love, Success and Everything In Between

Note: These ideas have been shared with me over the last three years in response to a simple question: “What advice would you give your 20-something self?”

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.

Ben Sands

Author Ben Sands

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