How do I deal with the upgraded problems of being a leader?

September 24, 2024
3
min read

Not Career Advice is a monthly podcast and a̶d̶v̶i̶c̶e̶ coaching column that asks and answers questions about "making it" in your career—and what that even means.

You can submit your own question here.

The career question

Thank you for this. I’ve been taking a more active role in my life and with this came release and many challenges but also upgrades.

In my career of voice acting/narrating and my lifework of running a social enterprise I am the founder and “boss”. While I am used to delegating by choice and circumstance, I’ve never had a title, eyes on me and responsibilities that came with it.

How do I flourish in being seen/in the spotlight and the boss? How do I release and walk through the fears that come with the title and responsibilities? And lastly what do I do with the possibilities of “failing” on a grand scale?

- Lindsay

The not career advice

Hi Lindsay,

As you’ve discovered, upgrading your life often means upgrading your problems. Fresh problems are a good thing. They’re mile markers of your growth.

Maybe you used to wonder if you’d ever make the impact you dreamed of. Now, you face the challenge of stewarding the influence and impact that’s at your fingertips.

*Oprah voice* Congratulations on your brand new problems!



As I read your letter, I came back to your use of the world title. It seems like it’s a weighty word for you. The title brings the fear and the eyes and the responsibilities.

I’m curious: what do you picture when you picture someone who holds your title? How similar or different is that picture to how you view yourself?

If my hunch is right, there’s a gap between who you are and the leader you believe you’re supposed to be.

So how about we aside the title for a moment and simply talk about how you’d like to lead?

One of my favorite things is helping clients develop their own way of leading. There are plenty of articles about leadership styles. (Here’s one for you to explore.) But those frameworks won’t replace your own reflection.

These questions will point you towards your own leadership style:

- What did I love about my favorite leaders?

- What did I loathe about my least favorite leaders?

- What support did I wish I had from past leaders?

- What type of leadership would help this organization create its desired impact?

Personally, the most impactful leaders I’ve had are the leaders who are fully themselves while also responding to the needs of the team. Easier said than done, right? Finding that balance of authenticity and responsiveness will feel wobbly for a while, but trust you’ll find your own sweet spot.

That wobbly place of learning a new skill is already vulnerable, and you’ve got the added bonus of learning in front of an audience. It makes sense that you’re afraid to fail.

So if you want to give your dreams and social enterprise a fighting chance, you’ve got to answer this question honestly:

Do I care more about avoiding “failure”, or do I care more about taking action?


I ask that question without judgment. Maybe avoiding failure wins out this time. If that’s the case, you know what to do. The only way to avoid the appearance of failure is to not try at all.

My guess is you believe this social enterprise is worth your action. In that case, here’s a failure reframe.

I often invite clients to think of their work as a series of experiments because you can’t fail experiments. You can only learn from them.

What would it look like to create a culture of experimentation within your social enterprise? Within your career?

Sometimes it’s as simple as saying, “We’re going to try this for six months and see what we learn.”

As the founder of the organization and the leader of your own career, you get to decide what it means to fail.

I’m excited for you, Lindsay. I don’t know what all’s in store for you, but I’m wishing you a lot of learning and more upgraded problems as you keep upgrading your life.

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