My $250,000 Mistake

Picture this: it’s Fall 2007 and I’m sitting in the backseat of my blue Ford Escape. I’ve got a GMAT test book in my lap and my math coach on speakerphone.

I’ve snuck out from my nonprofit job on my lunch break to sit in my car and practice GMAT questions. 

And “snuck out” is the absolute right way to put it, because no one – not my boss, my teammates, anyone – knows I’m hatching a plan to get out.

Oh, and I’m sweating. Because I’m in hiding, in my car with the windows closed, doing MATH.


Ashley’s Note: the story I'm about to tell you is about the expensive mistake I made when trying to create my exit strategy from a job I hated. If you're trying to craft your own exit plan, I can help you do it right (and avoid my mistakes) in my 4-week coaching career strategy accelerator. Read more and get on the waitlist.


After finding myself in yet another job that I hated – a series of roles that looked good on paper but didn’t feel aligned, honest or true to me – I threw a final Hail Mary and decided to go to business school.

My best friend had gone to b-school the year before. She was smart and had her sh*t together. So maybe that’s what I should do, too, I thought.

Ooof. That was an expensive mistake.

Don’t get me wrong: I don’t regret getting an advanced degree. But if given the chance to go back in time, I would counsel my younger self to think differently about the moment she’s in.

What would I tell Younger Ashley if I could? I’d actually start by asking her a question:

“What’s the smallest, cheapest, fastest thing you could do or try to learn if getting your MBA is the right thing for you?”

If we use my story as a case study, can you see how quickly I jumped from “I’m extremely unhappy” to “I have to take drastic, radical action?”

This is so common – and totally understandable. The pain and discomfort we feel when we’re in a misaligned or dead end job is exactly that: PAINFUL.

Which means we often jump straight to the clearest, neatest solution – one that is well-tested, understood, and often really, really dramatic. 

Over the years I’ve come to see career planning and big decisions through a different lens. 

Namely, iteration.

Instead of jumping to the easiest or most explainable solution, I instead ask myself (and my clients) to iterate:

What’s one thing you could do or try right now to learn more about this option – before committing to it?

When we ask ourselves this question, a couple of cool things happen:

First, our goal shifts from being ‘outcome-driven’ to being ‘learning-driven.’ We’re not pushing ourselves to make a decision or a choice on the spot; instead, we’re taking intentional steps to vet this choice.

As we shift our focus to learning instead of outcomes, the pressure we feel shifts, too.

Radical action (like declaring I’m going to business school without actually considering how much math I would be forced to do) puts a TON of pressure on our choice. It raises the stakes – and sets us up to feel like a failure if we don't ‘get it right.’

But when we shift our focus to learning through incremental action, our entire orientation to pressure changes. 

Suddenly we can see that we’re actually DE-RISKING our decision, because we’re trying it out in small bites.

What would this look like for my Younger Self? Well, I wish I had started by exploring the curriculum first. This might have looked like taking an econ 101 course at the local community college, or spending a day shadowing my friend at her business school. 

With incremental steps like this, Younger Ashley would have not only collected important data to inform her decision, but she would have created an important check-point for herself: “Ok, I tried out this econ class and I hated it… what does that tell me about my overall interest in the business school curriculum?”

I don’t blame myself – I was making the best choice I knew how to make at the time. And the pain of being unhappy in an inauthentic role was just too much for me to bear.

But man, I’d do it differently now. Which is why I want you to learn from my mistake!

If you’re feeling unhappy at work and hatching your own big plan to get out – I encourage you to ask yourself the same question:

What’s one thing you could do or try right now to learn more about this option – before committing to it?

Start with that question and take one, iterative step forward. See what you learn. Then decide the next small step to take.

Trust me, your Future Self will thank you for it!

Onward,

 

PS: Are you ready to create your career plan using iterative action? I can help you craft your exit strategy, pivot into your next field, or prepare for your next leadership step in my Coaching Strategy Intensive.

Read more about how it works and get on the waitlist to be notified as spots open up!

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