What If You're Scared of Success?

Fearing failure is the standard conversation; fearing success is the real obstacle

Chapter 7 of Start Finishing, “Keep Flying by Accounting for Drag Points”, deals with the tension between the velocity and momentum we want, and all the factors in our lives that slow the speed we want to create (and hopefully sustain).

As I say at the start of the chapter, “Rather than gravity and wind resistance being the dominant forces creating drag [as in physics], people tend to be the dominant sources of drag for your project.” One of the questions I continually am asked about Start Finishing is: how could these ideas be applied for leaders, or in a team setting? That’s how Team Habits was born. It’s important to consider the ways our beliefs and blocks about personal success might also affect the larger success of our teams.

Whether it’s a personal project or a team project, our social dynamics and projections can hold us back — in particular the fears and anxieties we have around success. 

[The following is a modified excerpt from Start Finishing.]

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When we think of no-win scenarios, we tend to think of especially dramatic cases: movies and shows where the hero has to make an impossible choice usually involving a choice between saving a small number of people versus a large number. 

Extremes make for gripping entertainment, but those aren't the types of no-win scenarios I want to talk about. I’m talking about the everyday scenarios, where we tell ourselves that to be successful in our work or lives, we have to give up something important to us. 

While there are any number of specific no-win scenarios we create for ourselves personally, there are three general kinds that always seem to show up:

1. The Success Will Cause Relational Harm tale (with families, friends, or in our community)

2. The Success Versus Virtue myth

3. The What If I Can't Do It Again? trap

Before I discuss each type, it's important to realize that the creation of no-win scenarios lurks underneath so many of the ways we visualize, plan, and execute the plan. 

When it comes to visualization, too often we won't allow ourselves to visualize what our life and work might be like in a best-case scenario, because there's a near-reactive flinch away from what's possible — into something that seems more comfortable, doable, and safer. 

During the planning process, this block comes up because we give too much weight to the failure we're counterposing against the success we're imagining. And, lastly, it comes up in the execution because we fail to play the game to win, in the interest of trying to mitigate or prevent the failure that we assume will come with winning.

This drag point is thus really critical to address from the beginning because, if you don't, it's going to be the unwelcome gift that keeps on giving. Fortunately, once you see the no-win scenario you've created or accepted, it's simple to defang. (Remember, as usual: simple does not equal easy.)

Myth #1: Success Will Cause Relational Harm

We all know someone who estranged themselves from their family, friends, and loved ones because of their (supposedly) single-minded pursuit of success. We've also experienced scenarios where somebody excelled and others got hurt, bitter, or envious about it. Whether it was the smart sibling whose success was used as a yardstick for other siblings, a friend who got the hot girl/guy that the others pined for, or the promotion that created a wedge in your work buddy group.

Because the fallout of these occurrences is so common and devastating, it's easy to encode a story that looks like "If I win, I hurt someone."

This is a particularly troublesome story for women. The same culture that creates unnecessary zero-sum games, also idolizes gentle and kind women, with the result that it can be as internally hard for women to chart their path to success as it is externally hard to remove the barriers that make it hard for them to do so. Often you have to work extra hard to be more qualified than your male peers and deal with additional expectations (whether of being a mother, a partner, attractive and successful, etc.) And it's not as if it's just mothers who have a no-win scenario; we socialize women to be the kin keepers, relationship tenders, schedule bosses, party throwers, community welcomers, and a whole load of unpaid labor that, if undone, leads people to judge and ostracize them. 

The difficulty with untangling this particular no-win scenario (“Success may/will cause relational harm”) is there are shared expectations that need to be addressed… because relationships are shared expectations. One party may not want to let an expectation go or see that their expectation is preventing your self-actualization. 

Furthermore, there’s a possibility you may be in relationships with people who consciously or unconsciously don't want you to grow and flourish because of their own insecurities, needs, and shortcomings. 

We don’t get to decide our life in a vacuum but we also can't blindly accept the definitions and expectations others have of us, either. It’s all too common for people to expect or want us to be the supporting character in their story. 

To be clear, we're all supporting characters in each other's stories, but we're not solely supporting characters — and too many people don't allow themselves or get to be the stars in their own stories.

To untangle this one, you're going to need to practice Intention, Boundaries, and Courage — in much the same way that you handle Other People's Priorities. Only with the additional difficulty that it's often hard to tell the difference between other people's priorities and your own priorities when it comes to deep core relationships. 

Myth #2: The Success Versus Virtue Myth

Another absurd no-win scenario is the success versus virtue myth, and there are a host of variations on this one. The most common one we see is the Starving Artist Myth, which counterposes creativity, authenticity, or craft with financial success. If your art starts selling well, it means you've sold out. So the story goes.

A second variation of this story is some version of "nice guys finish last." Yes, this is very similar to the previous "If I win, somebody is hurt" no-win scenario, but it switches the focus from harming others to harming your own integrity or virtue. Better to be a person of character and not win than be a winner who sacrifices her own character.

[Following the “nice guys finish last” logic is the “Success Will Wreck My Health” fallacy: where the concern isn’t for our morality, inner selves, or immortal souls, but for our physical self and well-being. The presumption is: “If I succeed I’ll deplete my mental, emotional, spiritual, and physical resources.” This no-win scenario revealed itself after the publication of Start Finishing, but I’m excited we could add it to the Start Finishing Field Guide (page 76).]

And, of course, there's the "rich people are bad people" mindset that runs prevalent in our culture. Rich people, the story goes, must have cheated, stolen, oppressed, manipulated, or generally schmucked their way into wealth. That some religious and spiritual traditions reinforce this only adds to the truthiness of the story.

In each case, some success state (wealth, achievement, fame, power, influence, etc.) is pit against some virtue (honesty, generosity, authenticity, creativity, kindness, etc.). To have the former, you have to compromise the latter. Or, even worse, if you work your way into having the former, you have to feel guilty or unsettled by it and work harder to make sure you're being a good person.

It's true that we have plenty of examples who have managed to accrue success who have gotten there at the cost of their integrity. People will sell their soul for a buck. People will step on other people's necks to get four inches ahead. People will cut corners while still selling the square.

But there's no necessary connection between the two. There are plenty of examples of people who are successful AND integrous. There are also plenty examples of people of unsuccessful people who lack character.

Lincoln said:

“Character is like a tree, and reputation like its shadow. The shadow is what we think of it; the tree is the real thing.”

To extrapolate the point, success doesn't alter one's character — it simply reveals your character. It can also test your character. The more successful you become the more momentous and impactful your choices will become, at the same time that more people will want your attention and resources.

To untie this particular no-win scenario, then, requires reframing the tension. Here are three simple questions that may help you do so:

1. Who is a model of someone who has managed to be successful and virtuous? Your models will be different and they can be historical or present. If they were able to do it, why can't you?

2. Consider what virtue you think is in jeopardy. What specific action or behavior would be a violation of that virtue? Is it necessary to do those actions or behaviors in order for you to be successful?

3. How might winning or being successful allow you to be more virtuous? Would you be better able to support or engage with what matters most to you?

You're too damn creative and resourceful to believe that you can't be successful and a good person. Yes, be on guard for missteps of character, but don't assume that you must take them to get ahead.

Myth #3: The "What If I Can't Do It Again?" Trap

This version of a no-win scenario is a particularly insidious one. Ironically, it’s often folks who find themselves doing well without much effort and preparation who are susceptible to this — a classic trait of Creative Giants. While we know there's a big difference between the results when we actually show up to win versus coasting, that knowledge and the practice in reality of coasting end up working against us. If we really stand tall and be seen for what we can do, we'll set a high standard that, gulp, we may not be able to do again.

To prevent that second failure, we pick a success level and amount of effort to ensure that we can top ourselves in the future. The upside to this is we also don't have to choose what we'll be truly excellent in. We can continue to dabble and continue to be better than the average bear and continue to collect our hodgepodge of third place trophies with the smug, knowing grin of how much harder the people who won first and second place worked.

The reason this particularly no-win scenario is so hard to untie is because deep under the top-line question of "What if I can't do it again?" there’s a fear of losing the fun and freedom that comes with being a dabbler and polymath. Mastery and excellence require continual work, failure, and intention — we have to dig in after it's fun, to sweat the details and execution, in order to get to the different kind of fun and freedom that comes with being an accomplished master of our crafts.

The "What if I can't do it again?" trap overlooks that along the way we'll accrue more experience, people, and resources to do it again better next time. Of course, we'll also escalate our goals and project scope, but that's what it means to be in the arena. At any given point in our lives, we're better than we were two months ago. Just as we should assume the sun will rise tomorrow because it rose today, we should also assume that we'll be two month's better two months from now.

So, perhaps it's true that this current version of yourself will not be able to do it again. Luckily for you, the better, stronger, and wiser version of yourself, playing their best game, will probably be able to do it. Success is cumulative — the shots you take today don't take from the shots you'll have in the future, they add to them.

Have the courage and faith that when the next dragon comes, you'll be able to slay it. Despite what it can sometimes seem, the fact that you've made it here is evidence that you can make it to there.

Lastly, you might fail next time 'round, but better to try something with all of your heart that might not work than to continue to go for the easy wins. Do you really need another third place trophy?

Transcend the Safe Play of Mediocrity

The most rational way to approach no-win scenarios is to pursue the path of mediocrity. (In case it's not clear, I want 'mediocrity' to sting so that — even if you choose to take it as the safe option — you're still aware of the sting.)

But why is it the safe option? Let's take a look at the two prongs of no-win scenarios the way we've been talking about them. Avoiding failure needs no real explanation. No one wants to fail or be embarrassed or be humiliated.

But, when you have one of the beliefs above about success — that it'll cause relational harm, that you'll have to be less virtuous, or that you'll eliminate your ability to be free or have fun — then those are some dragons we'll also want to avoid, and the only way to avoid them is to be just successful enough to not risk them. If you stay far enough away from the dragons, they can't bite you.

The sad truth is that there's likely a small number of people in your life who'll get mad, upset, or frustrated by your mediocrity, especially if your mediocrity is tied to your being attentive to their needs, priorities, or goals. They will get mad, upset, or frustrated by your failures, and they may get mad, upset, or frustrated by your success.

Thus, mediocrity is the safe play. No dragons can bite you, and you won't create more dragons when you overcome the one in front of you.

Mediocrity being the safe play is only partially true, though. It's true in the short term and in the day-to-day decisions and compromises you have to make. Keep your head down, check the block, avoid the heat today.

But in the long run, it's the worst thing for your thriving in life or your career. Whose work do you remember that is a product of their keeping their head down, checking the block, and avoiding the heat? What important change in our culture has come from that?

We’re no more able to thrive by being mediocre than a fish is able to thrive in a shallow puddle. Sure, the fish may survive, but until they connect back with the deep waters and others of their school, they'll always be a sunny day away from disaster.

We don't overcome no-win scenarios by choosing mediocrity; we overcome them by breaking the internal rules that create them. Swim, fish. Swim.