Ever Ask Yourself: How Did I Get Here?

by | Apr 22, 2014 | Defining Success | 30 comments

E veryone will tell you to fake it until you make it.

Few will admit how often they feel the need to fake it once they’ve made it.

Take Monica, a former client who pulled herself out of poverty. At times, her family was homeless, and her childhood was marked by instability and fear.

Now a lawyer and COO of a major organization, there is no doubt she’s overcome tremendous odds to “make it” in the traditional sense. She does important work, she is respected by her peers, and has the ability to financially support her family. But it has all come at a price.

A price, she realized, she never consciously made the decision to pay.

She works long hours, she pushes past her fears and insecurities, and she’s done what she felt was right for her organization, even when it wasn’t popular.

And it often leaves her utterly exhausted.

She doesn’t have time for friends. And she certainly doesn’t have time to find a man, settle down, and start the family she’s always dreamed of. In fact, the further up the corporate ladder she’s climbed, the more isolated and lonely she’s felt.

When I asked her to describe one person who epitomized success to her, this is what she told me:

My Uncle started an interior design business in the late 70s, early 80s. He grew this business while investing in the development of his children, helping me (he took me in when I had no place to live), supporting our annual family reunion, and supporting businesses he believed in. He is hard-working, generous, family-oriented, dependable, and kind. I do not believe he has what most of us would consider a large salary, but he leads a simple life.

What became clear is that although she’d come a long way, there was still a huge gap between the kind of life she desired and the one she was living.

If you’re going to work your butt off, take a little risk, and put your talents to use, shouldn’t you at least get the life you actually wanted in return?

I say absolutely.

Unfortunately, most have no idea how.

The Success Crisis

In his book Springboard, Richard Shell reveals a similar experience.

He describes six different fictional lives: There’s the wealthy internet entrepreneur who parties around the world, now solo since his divorce. There’s the tennis pro who adopted three kids with her husband, but laments the professional circuit doesn’t give her as much time with family as she’d like. There’s the stone mason, who admits that times are occasionally financially difficult, but he derives so much pleasure and pride from his work (especially building houses for his children), he’s happy and content. There are three others, all with their own mix of trade-offs.

Shell then instructs his clients to rank these profiles, from most to least successful. And what’s fascinating is that among the hundreds of business school students, Wall Street executives, doctors, and government officials he’s worked with, the most popular choice for “most successful” by far is the stone mason.

Just as I found with Monica, Shell discovered there is often a huge gap between what these esteemed, accomplished people seem to admire and what they pursue for themselves. Monica is not an anomaly among overachievers, she’s the norm. And the question is: why?

How is it that those who have an abundance of talent and drive, and therefore opportunity, have such a difficult time creating a life they love?

The Goldilocks Strategy gets it “just right”

Part of the answer is what we talked about last week in the review of Greg McKeown’s book Essentialism. More opportunity often equals more diffusion of effort and ultimately, less clarity about what’s important.

But it’s more than that. The other problem stems from the messages we absorb about what success is and how to get it.

There are two camps when it comes to giving advice on success. The first is the “Go big or go home” camp. They see life like a battle, filled with an endless series of skirmishes that you either win or lose. They value ambition, competition, and impact above all else.

The second is the “Less is more” camp. They see life like a wild garden that needs to be pruned and trimmed to reach its full beauty. They value gratitude, simplicity, and mindfulness above all else.

The problem is, for most overachievers, neither of those approaches to success work very well.

The “Go big or go home” camp just fans the flames of overachievement—along with feelings of inadequacy, anxiety, and fear. Because the competition is endless, the sense of having won is short-lived while the exhaustion becomes chronic.

The “less is more” camp sounds nice (particularly when you’re tired of competing), but it’s so different from the lifestyle overachievers are used to, it’s difficult to maintain. It feels like they’ve given up and dropped out. An overachiever enjoys competition and challenge; they just don’t want it to take over their life.

These can be thought of as two extremes of an achievement-oriented spectrum. For the overachiever, one is “too hot” and the other “too cold.”

And that means there’s a vast middle of “just right” which very few people are talking about, much less discovering.

That’s why the Monica story is so instructive, and so common. There is absolutely nothing preventing her from designing a career and life more like her Uncle’s. But given what she’s professionally capable of, others tend to push her towards the “Go big” camp, while a change to the “Less is more” camp feels too drastic.

What she needs is some clarity on the middle ground, something that brings elements of her Uncle’s life into her own, without sacrificing the gains she’s already made in her career.

The difficulty is that the range of options in this middle ground is huge. What you need is a strategy to define “just right” for yourself. Then, and only then, can you figure out how to realize it.

For example, Monica spent an entire year focusing on friendships. She changed jobs a couple of times, trying to get the right mix of professional challenge and time outside of work. She’s still tweaking, but now she can see she’s headed in the right direction. She’s building a community she loves.

And that alone makes her feel more confident and more successful.

Just how serious are you about success?

Professional musicians spend time understanding and implementing music theory. Doctors never stop studying what makes the body tick and the tools they can use to fix it.

And yet, how many of us lose hours and days of our lives, worrying if we’ll be successful, without putting in the time and effort to really understand what success means? We endure a self-induced agony and never ask for the help we need. If you’re struggling to feel successful, you have to ask yourself:

Are you willing to do a little work to actively set the direction of your life?

Are you willing to experiment to see what really makes you proud, motivated, and happy?

Are you willing to pursue your ideas, even when others call you crazy?

If so, congratulations. Having an inquisitive mind and the courage to break new ground are essential to finding the success that fulfills you.

But you don’t have to do it alone.

Next week, I’m launching The Overachiever’s Guide to Meaningful Success, which will walk you step-by-step through creating a personal definition of success and developing a new set of metrics to keep you on track. I’ll also be opening up a very limited number of seats to our Luminaries Club, a small mastermind dedicated to helping its members find (and stay true) to their “just right” definition of success.

The way I see it, either you dedicate yourself to an ideal or you stop complaining about it.

If you want to do more than just boast and impress, if you want to feel success in your bones and use that confidence to inspire others around you to do the same, you absolutely can.

First, you have to believe it’s possible.

Then, you have to put in the work to make it happen.

Let’s do this.

See you next week.

***Editor’s note: The Overachiever’s Guide to Meaningful Success is now here!***