During the final semester of my MBA program, I wrote up a case study about Apple for my Business Strategy course. Unsurprisingly, I waxed passionately about Steve Jobs’ success and the opportunity we each have to lead lives of significance. When I got the paper back I had good marks, but my professor, Dr. Michael Crooke, also left a puzzling comment: “Relax!”

“You’re already successful,” he continued.


Instead of the settling effect I’m sure he intended, Crooke’s comment catalyzed the arbitrage in my head! Successful!?! How did he figure? Sure, he feels successful! He led a beloved multinational corporation with nearly a billion dollars a year in revenue (Patagonia/Lost Arrow), was on the short list to lead Bono’s Project Red, and is well-respected on the international business landscape.

I’ve …  Well, some days it doesn’t feel like I’ve done much of anything!

Still his conviction forced me to wrestle with the question: How do you know when you’re ‘successful?’ Is ‘success’ internal or external (i.e., a feeling or recognition)? Is it a journey or a destination (i.e., a process or an event)? Though my search for answers admittedly continues, here are three truths about success that have helped me wrap my head around the concept and be more appreciative of my own accomplishments. I hope you find these ideas helpful and encouraging too!

  1. Success is Inherently Subjective – Stop and think for a minute: How do you actually measure ‘success?’ Is net worth the best proxy? Society might have implied so 30 years ago, but today? How about buying power? Living in the United States (and Los Angeles, in particular) this seems to be a more commonly accepted yardstick: Who cares if you have money as long as you look like you do! But what happens when you throw a country like Bhutan into the mix? They literally measure Gross National Happiness! What a paradigm-shifting concept! We all know people with material success who remain unhappy nonetheless.
  2. Your Target Always Moves – Hitting a stationary target is one thing, but a moving target is quite another – and ‘success’ is definitely a moving target! Like it or not, there is always a new incoming class with sharper, younger minds; A faster, sleeker dream car; A bigger house, new all-star, A-list actor, hot band, and Silicon Valley rags-to-riches phenomenon! It’s true, and the list goes on. In our dynamic world, nothing remains static long enough to catch it. Instead, even our best attempts are like trying grab a stream of water! As Solomon wisely observes in Ecclesiastes 2:11, “But then I looked at what I had done, and I thought about all the hard work. Suddenly I realized it was useless, like chasing the wind.” (NCV).
  3. The Answer is ‘Yes’ – While trying to identify a target, it’s also worth trying to figure out who is keeping score and where the finish line is located! Has your head started to ache yet? In reality, nobody else defines ‘success’ consistently either. Hence the answers to the hypothetical questions posed above are always ‘yes.’ Success is BOTH internal and external, related to your feelings about yourself AND recognition by other people. Success is also both a journey and a destination, a process with important milestones along the way.

Thus far, one of the things I have realized is that we must each define ‘success’ for ourselves. Why? Because developing your own definition of what a successful life looks like is the only way to encapsulate its many facets (e.g., physical, spiritual, material). In addition, since ‘success’ is definitively multifaceted, being successful in areas of importance to you will necessarily require tradeoffs in other areas. We each have limited time, energy, and money to invest, so our choices implicate opportunity costs. Consequently, defining success for yourself will also allow you to measure your progress, determine whether you are succeeding in the areas most important to you, and make changes if you’re not.

“Success bases our worth on a comparison with others. Excellence gauges our value by measuring us against our own potential.”

– John Johnson, Christian Excellence

So, how do you know when you’re successful? First, you define success for yourself, and then you act intentionally with that definition in mind. You make the rules, and officiate the game. Yes, this does mean that you can cheat! You can take credit where you don’t deserve it, or reward yourself for slacking. But why would you? You’re already positioned to win!

Editor’s Note: If you’re currently wrestling with your definition of ‘success’ let me recommend the following resources: Michael Hyatt’s free eBook Creating a Personal Life Plan and John Maxwell’s book Put Your Dream to the Test. I spent five months painstakingly working through each of these books, consolidated the results, and then discussed them with several mentors. As a result, I have a well-developed road map that articulates my values and dreams, provides criteria to contextualize decision-making, and helps keep me focused. I consider it the best investment of time I have made in the last four years, including all the time dedicated to the pursuit of both my JD and MBA degrees!

Leave a Comment: What challenges have you wrestled with in coming to terms with the concept of ‘success?’ How will you know when you’re successful?

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