I’d turn down my 2018 dream job today
READ TIME: 3 MINUTES
Last week started the way every parent knows when the seasons change: sick kids.
Which means no daycare.
My partner covered an hour so I could work. Then we switched.
Somewhere in there, I tried not to fall behind.
In 2018, my weeks looked different.
I’d just become VP of Sales at Schoology, and with it, I took over my first enterprise sales team.
I flew to California 6 times that year. I turned work trips into long weekends in Austin and Napa, and I played in superintendent golf tournaments.
I loved every bit of it.
Today, that same role would be a dealbreaker.
Not because the job was bad. Because my life changed, and what I need from work changed with it.
Taking it now would mean building a completely different care setup for our kids.
That’s where every search should start. Not with the title or the logo. With how the role fits your life and your goals right now.
And you find that out during the interview, not after you join.
You're the buyer too
Think about how you run a discovery call. You don't pitch the second the prospect picks up. You qualify. Is there a fit? Does the timing work? Is this worth both of your time?
Most candidates skip that step in their own search. They walk into interviews trying to win, not trying to qualify.
The right move: run the interview like discovery. They're vetting you. You're vetting them.
The more you think of it that way, the less pressure you put on yourself. The nerves fade, and you perform better.
Build your qualification criteria
You can't qualify a deal without criteria. A role works the same way.
Write down what matters today: comp, travel, flexibility, team, sales cycle, manager, growth path.
Rank it. Mark your non-negotiables.
Check it against your last search. What moved up? What fell off?
Early in my career, I wanted 2 things: money, and to stay in DC, the city I loved, with my friends. No travel. No face-to-face client meetings.
A few years later, I was booking flights to California and loving it.
Today, flexibility sits at the top.
Each version was right for its moment. The mistake would have been running today’s search on any of the old ones.
Bring the list into the room
Turn your top 3 priorities into interview questions.
If money is #1, ask: “How does the commission plan work? What are the top reps earning?”
If flexibility is #1, ask: “What does a typical week look like for the AE who hits quota? And if something comes up at home and they need to step away for an hour or two, how does the team cover?”
If travel is #1, ask: “Walk me through what travel looks like in this role.”
If quota is #1, ask: “What percentage of the team hit quota last year?”
If growth is #1, ask: “If I come in and perform, what does career growth look like here?”
Then listen. Does the answer line up with what you’re vetting for and how you ranked it? If it doesn’t, be willing to walk away.
I’ve watched clients ignore that gut check, take the offer, and know within 2 weeks they’d made the wrong call. 6 months later, they’re back in a search, explaining a short stint on their resume.
Walking away from an offer is uncomfortable. Explaining a 6-month stint is harder.
In 2018, the right role put me on a plane to California. Today, the right role lets me stay home when my kids are sick. The right role isn’t the first offer. It’s the one that passes your own qualification criteria.
Hit reply and tell me: what's at the top of your list right now that wouldn't have made it 5 years ago? I read every response.
To clarity and confidence in your career path,
Amanda
See you next Sunday.
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