This question will ruin your career
Should I stay or should I go?
Should I leave my job or stay?
It seems like a productive question, right? It smells of sweet reflection, of Elizabeth Bennet standing atop a cliff all earnest and pensive, evaluating her life from on high.
Then there’s it’s tricky sister: when do I know it’s time to leave my job?
Both versions masquerade as helpful while luring you into unproductive decision-making frameworks:
Making emotion-driven decisions AND execution plans.
Taking a lateral move based on a promise that—if you were looking at the situation objectively you’d know—won’t result in the upward motion or promotion you were promised.
Accepting big offers that—if you were looking at the situation objectively you’d know—are high-potential for long-term downsides, based on the role expectations, leadership, product, salary breakdown, etc, etc the list is long.
Accepting jobs you’re not excited about, because you think it’s the best you can get
Dive straight into the episode
What Do You Actually Want From Your Job? In this episode, we reflect on our careers and the decisions that helped us advance to senior-level marketing roles, CEO, and then to successful consulting careers.
This question is problematic, because it focuses you on current state and known options instead of inspiring you think opportunistically about your career and future.
A better question to ask:
If you can't articulate what you want, you will end up with defensive conclusions and decisions that may avoid the things you DON’T want, but they also don’t necessarily lead you to what you DO want.
When you identify things that make you happy, challenges you get energy from solving, how much money you want to earn AND how many (reasonable) hours you want to spend making it, etc etc., you enable yourself to start making decisions that serve your unique desires and circumstances.
Thinking from this perspective helps you avoid the “shoulds” and “should nots” and centers you on evaluating based on your aspirations, values, desires and boundaries.
There is no should or should not. Only choice.
This is what we’re exploring in this week’s episode. Replacing “should” with your own unique job/career criteria, so you can orchestrate your career decisions around achieving what you want for yourself.
New podcast: Good Boss, Bad Boss
When Joei Chan, Dir of Brand & Content at 360 Learning, reached out to me (hi, this part’s from me, Devin) earlier this year about launching a podcast about leadership and the complexities of being a boss, I was psyched.
I was already a fan of her award-winning docu series, Onboarding with Joei about her experience starting a new job at a hyper-growth startup right before Covid. She was blunt about the challenges she faced, her fears/concerns and thinking behind her decisions.
That raw, honest style, it’s not an act, that’s who Joei is, so I knew her pod would be interesting.
Joei and I met in NYC in February 2020, when she was evaluating Animalz to support her in her new role at 360 Learning. I remember her showing me rough drafts of her marketing plans, and feeling energized as she explained her strategic thinking for marketing and managing executive team to establish trust and get buy-in.
She was fearless and goddamn brilliant. I was humbled and energized. Naturally, I asked her to be friends 😇
Years later, she made a podcast, and it’s great. It is also complimentary to the discussions we have on Don’t Say Content, so if you like our podcast, I recommend listening to hers. My fave ep so far is her own story about a nightmare boss experience from from her past.
I know what you’re thinking, but I promise: this isn’t part of a partnership deal, she didn’t ask me to share it, and I’m not doing this as a friend. I just plain like Joei’s pod (also produced by Share Your Genius!) and think it’s useful to leaders and their teams!
Have a great weekend, everyone!
Love you bunches,
"high-potential for long-term downsides" is such a good label---and one that gets ignored far too often (been there, done that, etc.)