What If You're Not an Underdog?

Continually proving yourself to people who don't need the proof has a high cost.

In the game of life, we often see several types of victors.

Some are the showy type; they make a big ceremony about being there and winning and do a lot to draw attention to themselves. Others are more quiet; they're there to compete, improve, and win. Since the showmen are drawing such attention to themselves, those quiet winners are often underdogs.

It's not just the pregame show where they differ. The showy types, once they win, will do everything to remind you about how they won. They'll talk about adding this trophy or win to their other series of wins. They'll talk about how they will win the next one, too.

When the underdogs win, they quietly change into normal clothes or gear, cheer on a few other people, and then leave. If you weren't watching, you might never have known they were there. And they'll go back to practicing just as hard as they did before they won.

Dennis Rodman was a showman; Michael Jordan was an underdog. Oprah Winfrey, Richard Branson, Barack Obama, Dwight Eisenhower, and Abraham Lincoln were underdogs, as well.

The thing about underdogs is that, after a while, people start anticipating that they'll win. People start putting them in the "best-of" lists. Regardless of how they act, they're no longer underdogs.

Letting Go of Being an Underdog

I've always been an underdog.

When I was young, I was too poor, too black, and too white. As I matured, I was too smart, too dumb, too caring, too callous, too popular, too uncool, too athletic, and too unathletic.

In my twenties, I was too practical, too philosophical, too young, too inexperienced, too undisciplined, and too ambitious.

I recognize all the opposites that those sentences contain - I've always been enigmatic to people, even though, from my view, I'm not a complicated person. Complex perhaps, but not complicated.

No matter what I was trying to do, there was always a rather large contingent of people who told me that I didn't have what it took to do it. Earlier on, it was race and class issues and their second- and third-order effects that were at play. Of all the things you can change, you can't change the fact that you were born to a poor multiracial family in the South. The best solution to that problem was to get an education and get out of the South.

While I've never assumed I would be a failure, as I matured, I started asking better questions about what it would take to succeed. It turns out that someone else has already done what you're thinking about doing and they usually tell you how they did it. If you read enough stories about how to be successful, you'll see trends. Then all you have to do is put in the work.

My 30th year has shown me that it's time to let go of being the underdog. It was great for getting me here, but it's a canoe I must leave behind.

Overlooked (Again)

I was a bit upset earlier this week. I stumbled on a collaborative project one of my aspirational colleagues put together and saw that it was totally up my alley. A few of my friends are contributors, too. But I wasn't asked to contribute.

I was upset because I felt like I was overlooked. After I talked to Angela about it, I took a second look. Everyone contributing either has a traditionally published book or is friends with them. I don't have a book, and while we've met several times, I don't expect them to be calling me anytime soon.¹

There are broader issues here about expectations of inclusion in your friends' activities, but the main reason that I was triggered was because I saw a historical pattern at play. When you're an underdog, you get overlooked all the time - in my head, it was just the same thing all over again.

You know what? It was the same thing all over again.

Since we tend not to make a ruckus over what we've accomplished and how awesome we are, busy people who don't know us don't know about our accomplishments. Because I have spent so much of my time, energy, and attention moving, transitioning out of multiple career tracks, taking care of clients, and pursuing an alternative growth strategy, I haven't spent as much time as necessary displaying those trophies. How was Chris to know about all the behind-the-scenes stuff when they've been behind the scenes?

The fact that I'm hard to put a label on also doesn't help things. People with massive social networks don't have the cognitive space for round squares like me. Productive Flourishing is an expression of that complexity, to boot.

So, even though it was the same old “being overlooked” pattern at play, it was both not about me and also a consequence of my actions. There's no need to have a bunch of drama, but there is a manifest need to start revealing some of the things I've been sitting on for years. I've got some medicine to get out there and doing so will require some help - I can't do it alone, but to enlist people's help, they have to understand what it is and that it works. In the realm of entrepreneurship, we call this marketing and social proof.

The truth is that I don't need that project to write about the stuff that's up my alley. Productive Flourishing is my alley, and we can learn together here just the same. (Duh, right?!)

What If You're Not an Underdog?

I have many personal stories like the one above that would illustrate how believing you're an underdog and thinking like one gets in the way of your not being one. This post isn't just about me and what I'm going through - it's about you, too.

I know how awesome it feels when you've exceeded someone's expectations and "beaten" the sure bet. I know it's comforting not to have the pressure of performance on you. I understand the virtue of humility and "speaking softly while carrying a big stick," to paraphrase Roosevelt.

But what you should consider is how much of your precious time, energy, and attention are spent feeding the story of you being an underdog. How much head-trash, psych-outs, and lost opportunities will you endure at the hands of this self-fulfilling prophecy you're creating and perpetuating?

And, more importantly, how many people will you continue to miss out on helping because you're too busy playing the part of the underdog? Not only are you in your own way, but you're in their way, too.

If you can't tell, I'm writing this as much for myself as I am for you. I don't have it all figured out, but I invite you to join me in the exploration. Will you?

Here are a few places to start:

1. What would you do differently if you didn't have to prove that you're capable of doing what you're trying to do?

2. What are you waiting for permission to do, and what would it take for you to start with what you have right now?

3. What if, rather than being a pawn, you were the queen?

Your move.

1. 2024 Update: the project I was referencing here no longer exists, but my relationship with the person does. We don’t talk regularly, but we do check in with each other about every quarter.