Here’s a dumb-sounding thought: Trying to be successful will not help you become successful.

I know, I know, there’s a good chance that you’re rolling your eyes right now, thinking that the last thing you need is another article telling you the “secrets of success,” “how to make it,” or “the difference between winners and losers.”

I hate that stuff, too—all hyperbole, generalizations, and wishful thinking. But that doesn’t stop all of us from wanting to be successful, right? That’s probably part of the reason you’re here, to figure out your next move so you can get some of that oh-so-sweet success, or at least get one tantalizing step closer. You want to feel successful, and you want the emotional and (let’s face it) material benefits that come from it.

I love that. I love that you’re out there doing your best to make things happen, but there are five big reasons why focusing on success might not work out so well. Let’s take a closer look.


1. Success is a Moving, Amorphous Target

Be honest: What, really, is success for you?

Is it about launching a product or service and having people buy it?

Is it about paying off the mortgage and building a nest egg?

Is it about having respect from your peers, colleagues, and mentors?

Is it about doing what you love so you can care for your family?

Or is it something that kinda, sorta changes as time goes by?

Too often, we chase an idea of success that’s patched together from what we’ve read or observed or think we should be aiming for. Sometimes it’s built from what we’ve learned, and sometimes it’s based on the things you think success can deliver for you, extrinsic factors like lifestyle, property, status, or vacations.

When success is just a vague idea that comes and goes, changes shape and always seems out of reach, its amorphous, extrinsic nature makes it much easier to second-guess yourself. There’s no foundation to come back to and no compass to tell you where north is.

And even if you land some measure of success as a result of your efforts, you’ll feel disconnected from any sense of achievement it might offer. That’s why achieving the wrong kind of success will always feel hollow, because it’s only meaningful success—that is, your own definition of success that’s threaded with personal value, resonance, and meaning—that gives you a sense of intrinsic value.


2. Success is a Judgement

We’re taught from a young age to elevate success and the successful. Those who create multi-million (or billion) dollar businesses are splashed over magazine covers for us to idolize. Those who break new ground and innovate are revered as geniuses. And those who make it big are applauded as having made it.

Success is good. Failure, not so much. There are successful people, and then there’s the unsuccessful. We use these terms to describe and define more than we realize, with employers looking for previous successes during interviews, politicians talking in terms of their success and their opponents’ failure, and even movies either being critical successes or box-office flops.

Our judgements around success have even turned it into a consumer need, right up there with a house, a car, and 2.5 kids. It’s a need, drive, and focus based on unchallenged expectation that only spells trouble while it remains unchallenged. It’s a judgement that’s fatally flawed, leaving no room for grey, keeping eyes fixed forward, and not seeing the value inherent of all experience, regardless of meaningless labels.

Success isn’t a person, it’s simply something that happens from time to time. Stop judging success and failure as good and bad. Get past that and find the value.


3. Success Isn’t Here, Now

It’s easy to dream about the moment you become successful. We all tend to fantasize about the big pay-off for all our hard work, the moment when it all comes together and how it’ll feel to finally have made it. So it’s funny that this kind of success is always elusively around the next bend. Just a few more weeks or months away. Just one more challenge or goal. Just a bit more work, and you’ll finally be successful.

But where does that leave the right now? Feels to me like pinning your hopes on being successful in the future diminishes your value in the right now. It says, I’ll be complete when X happens, which is nonsense of course, because you’re whole right now, reading this.

Placing your sights on the horizon to a possible successful event can sometimes be a good motivator (in the short term at least), but you only get to play a great game if you’re willing to put on your tennis shoes, pick up that racket, and play at your very best right now, without knowing how things will turn out.

The present is where the action happens.


4. Success Doesn’t Result in Happiness

Research has shown that achieving career success doesn’t make you any happier. George Vaillant, a Harvard psychiatrist who directed a study from 1972 to 2004 into what it takes to lead a happy, purposeful life, plays down the importance of career success in making you happy. “In terms of achievement, the only thing that matters is that you be content at your work,” he says. And just to demonstrate what I’m sure is the remarkably obvious, his research makes it clear that even if you have a successful career, money, and good physical health, you wouldn’t be happy without supporting, loving relationships.

I know you know that, but underlying it is the simple fact that being “successful” does not change how your brain works. Your fears are still your fears. Your self-doubts are still your self-doubts. And your worries are still your worries. In fact, success can often layer additional layers of thinking on top of what’s already there. You might worry about whether you’ll ever be successful and have other thoughts and fears ripple out from that. You might wonder how you can keep the success you’ve already achieved going, or how long it’ll take before people figure out that you don’t deserve it. Or you might be afraid that you won’t be able to repeat it and be terrified that others will see you fail.

No doubt about it, success can tie your brain in knots and layer on second-guessing, self-doubt, and people-pleasing like throwing old carpets on a smoldering fire. What helps, then, is to get out from under those stinky carpets and make your next decision based on how much you get to be yourself and the value you get to create.


5. Success is Already a Limitation

Your perception of a successful outcome can only be painted by your own brushes. Which is to say, your sense of self, your sense of identity, your level of self-confidence, and the power that your doubts and fears have over you will all help to paint that picture.

If you don’t see yourself as the kind of person who can write a novel, you never will. If you think you’re too introverted to present to 3,000 people, you’ll exclude that possibility. If you don’t feel capable enough to go for that promotion, you won’t try. And should things go wrong, do you really want try for something you want only to fail and watch it slip through your fingers?

A vision of success comes with all of this other scary stuff, and is often tempered and shaped by it. If it’s too scary, you make it less scary, or you dismiss it completely. If it’s not “you,” you make it more you, something safer and more predictable. And if you don’t feel good enough or worthy enough of it, you set your sights much, much lower.

Real confidence is being able to trust your behavior with implicit trust in that behavior, in the full knowledge that you’ll be okay and whole no matter what happens. That’s where it’s best to invest your sense of self, not some half-baked definition of success, because it’s by simply taking repeated, meaningful action—regardless of how things turn out—that amazing things happen.


Photo courtesy of Mary Cunningham.