This week, I've been thinking a lot about career mistakes.

Not the usual suspects - a resume typo, a flubbed presentation to the executive board, forgetting your camera was on during a Zoom call, etc.

I've been thinking about the quieter failures, the ones that happen slowly, then all at once, the ones that eat away at our confidence until all it takes is a Slack DM from the wrong person to send us into a spiral.

The mistake of staying too long in the wrong job or under the wrong manager.

Let’s rewind to the late 2010s when mid-20s me landed my very first Marketo job with zero Marketo knowledge. Like, genuinely zero, had never even logged into the tool before.

The hiring manager knew this going in and I remain eternally grateful that they agreed to train me in the platform. What neither of us anticipated was the spectacular mismatch between who they were as a leader and who I was as a learner.

This person was great at their job. Wrangling the MarTech stack, building rapport with the sales team, slicing and dicing the data, it all came naturally to them.

But teaching and managing someone very early in their career? Totally different ballgame for them and one they struggled with.

And me? I needed someone who could teach not just the tool, but all the concepts of marketing operations and all of the professional working behaviors that most folks in their mid-20s just haven’t nailed yet.

I needed a lot. And it was too much for this person.

There were snappy interactions. Tense meetings and Slack exchanges. An endless fog of mutual frustration that neither of us could escape.

And just like that, after six months in, my manager found a new job. Overnight, I was reporting directly to the VP of Marketing, and everything changed.

This new manager got it. She understood exactly where I was professionally and technically, met me there, and then pushed me forward in ways that actually worked. She's still one of those leaders I try to emulate in my own management style.

I got lucky. I was saved by circumstance.

But here's the thing - most of us don't get rescued by accident.

Just this week, I had a coffee chat with someone drowning in their role. Smart person, solid technical skills, a good human being overall.

But after too many months, they finally realized the truth about their job: they had been set up to fail from day one.

Not because she wasn't capable. Not because she wasn't trying hard enough. But because there was a fundamental mismatch between who she was and how she operated vs what that company culture rewarded.

No amount of hustle was going to fix that equation.

This person’s story reminded me of another early career start-up job where I found myself crying in a bathroom stall after a tense interaction with an executive (who in hindsight was absolutely a jerk).

That bathroom breakdown finally gave me the motivation I needed to hit the gas on my job search.

But for all you reading this, don't wait for the literal or metaphorical bathroom breakdown.

Instead, continuously ask yourself:

If you scroll through my LinkedIn, you'll see I quit a job after seven months. Not because it was too technically challenging or because the team sucked, but because it wasn't right for where I was in life. It was a great job but just a great job for someone else.

So if you're unhappy at work, get specific about why.

Leaving isn't the only option. Can you get certain responsibilities off your plate? Or add a passion project that makes the rest bearable? Reduce your meeting load? And are you actually using all the PTO and health insurance benefits available to you?

And simultaneously, start building your financial safety net now. High-stress, high-stakes jobs need to be balanced with low-stress financial planning. Work towards paying off your debt if you have it and build up that emergency fund, that F* You Fund that gives you the power to walk away when staying becomes impossible.

The job market might be garbage right now, but that doesn't mean you have to accept being miserable indefinitely.

Sometimes the best marketing operations decision you can make has nothing to do with your tech stack.

See you next week,

🫶🏽 Alysha