How Fear of Doing Worse Holds Us Back From True Career Growth
Things will get more uncomfortable and worse before it gets better. Here's how to conquer your fear of failure and put yourself in positions to grow and win.
I grew up in a classic first-generation Chinese-American household where I was expected to be the perfect daughter, cousin, friend, student, sports player, family chef, and more. My parents’ mental model of life was that there are a finite number of winners. If you missed a quiz question, then you failed. Life was not a grading scale from A to F — only binary results of win / lose.
This made it difficult for me to take big risks. In a binary world, taking chances meant I might fail and ruin life as I knew it. It took me going to college and leaving the family home completely to tell myself a different narrative: risk-taking is essential for growth and outsized success. No one ever “made it big” by playing it safe.
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Fear of Failure Hinders Empowerment
I have clients (VPs and Directors) who secretly fear letting go and fully empowering their teams. I say secretly because they want their teams to do more and may even believe they are delegating well. In reality, they hold on too tightly to the process and outcomes:
they review too many details of their team’s work
they are a blocker in communications with leadership
they answer questions for their teams in leadership reviews
they jump in and redirect when there’s a hint of things going off-track
They look for everything to run smoothly. They fear messiness, uncertainty, and alternative ways of getting work done. They fear failure.
Fear of failure leads you to catch the balls for your team before they get dropped (making them feel less accountable).
Fear of failure causes you to work too many hours to stay on top of every decision and burn out.
Fear of failure means not prioritizing work that only you can do — the strategy and vision and advocating for your team’s needs.
To truly empower others, you get out of their way and put the accountability on them to come to you when they need support. You also need to get comfortable watching them make mistakes, produce work products of lower quality than what you could’ve done, or take longer than you may to solve a problem.
For those of us who grew up equating imperfection with failure, it is extremely uncomfortable to intentionally overlook imperfections in work where we are ultimately accountable. (I finch as I write the sentence). However, to truly empower your team and instill agency, you must create safety for failure — first for yourself and then for your team.
Play to win. Not defend from potential loss.
No leader ever resourced a project because of the lack of downside.
Too often, when pitching our ideas, we overly focus on addressing what could go wrong rather than highlighting the upside if it goes well. I’ve sat in too many product leadership reviews where we spend 10 minutes on the business value of a project, and the remaining 50 minutes on potential risks. Often, someone would ask a question that sounds very similar to “Why are we doing this” and we all have to remind ourselves of the upside again.
I see the same pattern in careers. In striving for perfection, we let others speak up on a topic we are not fully confident in, missing out on valuable opportunities to be heard. We pass on high-visibility projects in new areas because we are not 100% sure we can do a good job. In the classic innovator’s dilemma, we hold back on entering new markets or pursuing new business lines because they might not work out and we risk slowing down our existing business.
How to Create Safety for Failure
Now that you see the necessity of risk-taking and getting out of your comfort zone, let’s talk about how to do it.
Celebrate small wins: When you are learning new skills and putting yourself in new situations, count your successes and not the failures. If you’re learning how to ride a bike, you want to focus on the small improvements you’re making (e.g. getting on the bike, a few seconds of stability, a few first pedals, learning to turn), rather than counting the number of times you fell. Count and celebrate the progress you or your team are making, not the mistakes along the way.
Stop comparing: One of the biggest demotivators is over-valuing someone else’s successes. It’s hard to take a chance on imperfection and failure when you are anchored on someone else’s “overnight success”. Write your milestones based on your background and goals. Don’t live up to someone else’s standards.
Focus on the more important priorities: When you are delegating or empowering others and want to “jump in” to fix their work, remind yourself of your priorities. What are the things only you can do that have even higher impact? If you “jump in”, then you are deprioritizing those high-priority tasks.
Surround yourself with risk-takers: As the saying goes: “we are our five closest friends.” If you want to take more risks, make an effort to spend time with those who like to take risks. Their mindset, enthusiasm, and encouragement will rub off on you and make it easier to take that leap.
Final Note: Yes It Might Get Worse Before It Gets Better
The thing with taking risks is that you might fail. And things do sometimes get worse before they get better. And that is very uncomfortable but so necessary. When you or your team is learning how to do something for the first few times, it will be imperfect, messy, and slower. Smartly choose the projects and timing to help mitigate the downside. It may not be the best idea to learn to ride a bike during a thunderstorm. But don’t let waiting for the “right time” prevent you from taking the risk!
That’s all folks! See you next week at 3:14 pm.
Yue
Celebrating small wins is so important!
"For those of us who grew up equating imperfection with failure, it is extremely uncomfortable to intentionally overlook imperfections in work where we are ultimately accountable. "
So much "yes" in response to that. Especially if one replaces "we are" with "we believe we will be held"…