Breaking Free from “Up or Out”

“So… where do you want to be in 5 years?”

My stomach started to tense up in knots, but I knew my answer. There’s only one acceptable answer when you’re interviewing for a corporate role, or having a “development” conversation. I just had to say it, look natural, and act like I wasn’t faking it.

“I expect to be a senior leader at the company. I’m so passionate about my growth and the potential of this role and this organization.”

I uttered these largely false words when I was hired at my last company in 2018.

I had no desire to keep moving up the corporate escalator - but, don’t tell them that because you won’t get the job. However, I knew this was my last time playing this particular game before I was going to get out.

I’ve always existed in some kind of up or out scenario in my career.

Coming out of grad school, I got a job at McKinsey and Company, a Big 3 consulting firm. It was so exciting to have a career with the same kind of progression I faced in school: three years as an analyst/associate, then business school, then 3 years as a project manager, and then I get to shoot for partner!

What I didn’t realize at the outset was how little I wanted to be a partner. I was trapped on a project once where there just wasn’t any value we were finding… and yet the partner had to keep selling.

I didn’t want to fly across the country 2-3 times a week. I didn’t want to sell. I wanted to be deeply involved in the work.

But at McKinsey? The only option was to keep moving up… or transition out.

You couldn’t just stay a project manager because they needed to keep the pipeline of talent moving. Gotta create space for all that junior talent they want to hire every year from business school.

After leaving McKinsey and getting a job at Nike, I started the climb of the corporate ladder again. Moving quickly into a director role, getting a few moves into more senior roles, I was poised for the next leadership leap.

In order to get the promotions - or frankly any kind of professional development opportunities - you had to be ranked in the “hi-hi box”. We were all were classified by “high performance” and “high potential” categories, where high potential was where leadership could see you moving at least two levels up in your career.

But, as I looked up at the definition of success on the ladder, I didn’t want the tradeoff. I would be stuck in Sr. Director and VP limbo - making way more money but absolutely stuck in the political hell that I despised. My day would be even MORE filled with meetings to prepare for meetings to prepare for meetings, or meetings to recap meetings. I would never be able to turn off, or leave work at any semblance of a reasonable hour.

I loved the work at my current level, because that was the last level of the ladder where you got to touch real work, not just slides and meetings and political gamesmanship and navigating hiring freezes and layoffs. But staying at my level and growing in my role wasn’t an option; I would have been “taking up a seat that needs upcoming talent.”

I thought when I broke out of the corporate ladder, I would be free. Instead, I stumbled onto the entrepreneurship ladder.

Here’s just a sample of things I see every day.

“Six-figures isn’t enough - you need seven.”

“It’s harder to operate at $10K months than it is at $20-30K.”

“You’re not a real CEO until you can step away from the day-to-day and just let your team run it.”

“You should always be trying to work less while making more.”

And frankly, I was exhausted from the corporate ladder… and now there’s another one? I’ve actually seen some “paths of entrepreneurial success” that look like a ladder.

But under critical observation, I realized there’s still tradeoffs of climbing this particular ladder.

Yes, you can make more money if you keep moving up… and the status you gain is real. But as you move up, your business model shifts and there's both real benefits and non-obvious tradeoffs.

• Your role in the business changes, shifting more towards marketing/sales and team leadership. But, you can take on different projects or expand the spread of your work.

• The responsibility shifts from just you to being responsible for a team and a community, which you may love.

• You might be taking on more projects and parts of your business.

• The level of visibility you need changes.

• How you build in flexibility changes.

But for the first time in my career… I can stay at the level I want for this season. I don’t have to keep playing the up or out game.

I can stay as a solo consultant with some outside support.

I can prioritize building my network over building my net worth.

I can work at the pace I want that’s right for me, and not be trapped in some narrative about how much I work - both too much or not enough.

I can build in the flexibility to take my dog for a walk or write this newsletter during the day or on a Saturday! I can take off with Philip for a long weekend in New York City without really telling anyone.

I get to work on my craft, and hone my processes and positioning.

I can have creative bursts that don't go anywhere, or ones that get built in a weekend.

I don’t have to build a team right now. I don’t have to increase my revenue right now.

I can just… stay at the stage I’m at, doing the work I love and growing my capacity and capability to do this work well.

Or - shockingly - spend my time doing nothing of the sort and go read a book or take a walk.

And I have the optionality to change my mind about growth in a future season of my business.

When I left McKinsey and Nike early, I left millions of dollars of earnings and a heap of status on the table. I’ll probably never have a VP title. And I traded that money and status for time to meet my husband, snuggles with my dog, and more friends than I’ve ever had in my whole life.

But I made these choices because I’m playing a different game with my life. I’m not playing the up or out game anymore - I’m playing the infinite game, where “the objective is not to win—the objective is to keep playing.”

You too can step out of the up or out game.

You can choose revenue growth… or not.

You can choose to build a scaled or agency business model… or not.

You can choose newsletter subscribers or follower growth… or not.

You can step off the entrepreneurial ladder, and still have a business that's financially and energetically sustainable.

PS - want to craft your next business chapter that doesn’t assume more growth is the default option? You can book a Deep Dive strategy intensive, where we’ll look under the hood of your business - and help you make whatever path you choose more financially and energetically sustainable.