What does success look like, really?

What does success look like?

Not, what do we assume it looks like from headlines and soundbites.

But what does the journey to success look like, in reality?

When we think of successful people, we often mistakenly assume that their trajectory has been linear (up and to the right) – and that it all happened overnight.

In the book, The Startup of You, Reid Hoffman (founder of Linkedin) and Ben Ben Casnocha, do a good job dispelling this myth.

As they explain, successful career trajectories are bumpy and non-glamorous, except for a few timely breakthrough periods in which successful people experience explosive growth.

George Clooney, for example, was a struggling TV actor until he landed a role on ER and saw explosive growth. Years on ER then landed him his next high-growth opportunity in feature films.

Below is a graph of what we think success looks like (blue) and what it actually looks like (green).

Some observations about the reality of success:

  1. It’s more messy than we normally think.
  2. Most of the success can be attributed to intense, high growth periods.
  3. These high growth periods are a small minority of total time.

I can relate

I can very much relate to this (messy) picture of success.

In a matter of two years, I went from an Administrative Assistant to startup founder and COO.

Overnight success, right?

Yes and no.

I spent most of those two years hustling, day in and day out, doing non-glamorous work. My first small break was a promotion into a management position.

Then came my ER moment.

Two of my coworkers were starting a social gaming company and wanted me to run business operations. I had just been cast as a startup COO.

The next two years were spent running that company until we sold it to Zynga. Then I joined another startup, where I served as an executive for two more years.

During that four year period after I became COO, I grew in all sorts of ways – learning how to run a business, how to handle a board, how to manage an acquisition, and much more.

Still, from the outside, my trajectory was not explosive in the way that it had been when I first made the leap to become a startup COO.

Internally, I was growing like a mad man. By concrete measurements though, it was a period of noticeable, but modest growth.

Which brings me to now.

After ER, Clooney made the jump to the big screen. That was his next breakthrough opportunity.

Part of the reason that I have not taken a role operating another startup is because it’s a season for me to pursue my next breakthrough – my big screen debut if you will :)

For the first time, I am trying to build a business around my passions and my interests, as opposed to running someone else’s business.

It’s a far riskier (and scarier) proposition to do my own thing, but it’s the most satisfying way that I know of to keep my trajectory from flatlining.

Here’s a visual of my trajectory:

While the verdict is still out as to whether I’ll find success in this new venture, I take comfort in knowing that even Clooney had a number of less than blockbuster movie roles before really making it on the big screen.

Courting Success

Alright, we’ve adjusted our picture of success.

It’s messy and the glamorous “next-step” moments are important but infrequent.

Now that we know what it’s really like, how do we court it?

1. Put yourself in high growth areas – even at the expense of your pride.

George Clooney wouldn’t have been on the big screen if he hadn’t moved to Hollywood. I wouldn’t have seen such quick career growth if I had not fallen into the startup world.

If you’re going to get a breakthrough opportunity, you must first be in a place where breakthroughs happen. - Tweet it if you like it

If your company doesn’t promote from within or your industry is a sinking ship, get out!

Put yourself in a place of growth – a thriving company or a hot industry or even a friend group that provides positive peer pressure to achieve more out of life.

Note that to get in a place of high growth it will likely take sacrifice.

Recently, I’ve been approached by a number of people looking to break into the startup world. These are highly competent people with tenure in other industries.

Still, because the startup world is a competitive place to break into, my recommendation to them is to sacrifice title, pay, and status to get in the door.

This cost of entry is well worth it though. It puts them in a place where there is no ceiling on the success that they can achieve.

2. Show up, day in and day out.

Remember that, apart from a few high-growth periods, a successful trajectory is does not vary greatly from one day to the next.

These non-sexy, everyday moments though are crucial. They fuel the internal growth that you’ll need to seize those breakthrough opportunities and succeed in them.

Michael Hyatt has a quote that I love:

the ones who win are the ones who stay at it after everyone else has quit.

3. Take a risk and try something new.

Once you’ve experienced a high growth period, you will hit a plateau. That’s just how it works.

First, embrace the plateau, and work on your craft without worrying when you’re next breakthrough opportunity will hit. Show up, day in and day out.

Next and paradoxically, be aware of getting too comfortable.

While breakthrough opportunities are few, they are absolutely crucial for continuing your success trajectory. Moreover, breakthrough opportunities don’t come without risk and sacrifice.

If you feel yourself getting stale at your current level, look to take a risk and try something new. It’s the only way you’ll continue to grow.

And really, more than success, isn’t that what this is all about? Growth.

What are your thoughts? Does this picture of success resonate with you? Leave a comment.

Please note: I reserve the right to delete comments that are offensive or off-topic.

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12 thoughts on “What does success look like, really?

  1. Hey Ryan, I liked the post and the discussion of your personal situation. Kind of reminds me of what I was feeling after I left the corporate world a few years ago.

    I am big on personal growth, so I’m always thinking about the next big thing. Not because I “need” it to happen but because dreaming big and working toward a goal is really fun for me. I’ve thought a little about “getting too comfortable,” which is something that I used to worry about. My theory on this is that if you’re worried about getting too comfortable (like I was), you’re probably not in danger of that happening :)

    My experience has been that leading a stable and boring life is simply too painful and that I have to move on once I’ve been doing the same thing for too long. There are many people who “get too comfortable” but seem perfectly fine with it and don’t want anything else. That’s cool too.

    • Wow. Killer insight: “if you’re worried about getting too comfortable, you’re probably not in danger of that happening”. I think that’s really true and a healthy reminder for me to ease up on myself a little :) .

      Cool to see you doing so well post corporate world… and having fun doing it!

  2. Hey Ryan

    Great post. And the longer you stay at it, the more experience you get and the greater your confidence grows. This trajectory requires that we find a way to actually enjoy these un-sexy moments, as opposed to just looking at them as inconvenient steps to our end goal. Thanks for the inspiring reality check.


  3. I saw the author of the book/movie Abraham Lincoln Vampire Slayer interviewed this morning. (This is such an obvious concept–don’t know why someone didn’t do it sooner)
    He was saying how some see him as an overnight success and he pointed out how he spent years in his one room apartment writing things that noone was interested in. The key: he didn’t quit and finally he got his breakthrough.

  4. I read Ben Casnocha’s book My Start-Up Life and I loved it when he bets the reader that they have never failed as much as he had. Going outside of one’s comfort zone can be vulnerable and down right scary but it’s in those uncomfortable spots, in the unknown, in the risky move, that we can find those ER triggers. Easier said than done, but when a successful person tells you that it is perfectly okay and acceptable to fail, as long as you’ve learned something, it makes it a little easier for me to allow myself the possibility of failure towards success.