Iām Allison Stadd, drummer turned CMO, and I write for people who want to put the crackle back in their careers ā”
This issueās soundtrack:
Everything about my work life has been logical.
Iāve made color-coded spreadsheets to help me navigate job searches.
Iāve consulted mentors and recruiter friends before making any job change to ensure it would make my resume more compelling or minimally do no harm.
Iāve painstakingly shaped every sentence on my LinkedIn page.
Iāve catalogued career wins and learning experiences and honed them into well-worn stories to proffer in interviews and networking conversations.
When Iāve made career decisions based on heart or gut, itās been with the clean framework āhead-heart-gut-walletā a colleague early on gave me; i.e. even when navigating by feel, itās been formula-ized feel.
And all that logic and careful planning has served me well.
Iām proud of what Iāve accomplished over the last two decades, and I credit intentionality with a lot of that achievement.
Even when Iāve felt urgency or impatience around getting out of a gig and into a new one, Iāve resisted flailing.
I havenāt made professional impulse decisions.
Iāve always, as the cliche goes, run towards something vs. away from something.
My career to-date has been like cubed ice: tidy, structured, contained.
Now, amidst the Great Millennial Career Reckoning, I'm feeling the urge for career crushed ice: irregular, experimental, a little unruly.
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Work is serious.
Yes.
When weāre talking about earning money and securing health insurance for our families, thereās limited bandwidth for whimsy.
In Janel Abrahamiās 2026 State of Millennial Careers Report, financial freedom is the dominant millennial definition of end-of-career success, while financial pressure is cited as the #1 thing making careers harder right now.
And yet.
The work I feel most itchy for these days, as the sunrise of professional possibility has begun to emerge on the horizon for so many of us, is not logical, at least not by the standards Iāve used for the last nearly 20 years.
Iām craving more unexpectedness, more freedom and flexibility, more surprises; yearning for more āwhy-not-ness.ā
My two longest-held work dreams are 1) to publish a book and 2) to open a bookstore. I always imagined both way far out in the future, once Iād āfinishedā the full-time corporate portion of my career and could, I guess, luxuriate into a retirement of writing and small business management (?!).
But why couldnāt I pursue either, or both, now?
Why not explore turning this newsletter into a book proposal?
Why not investigate opening the Philly bookshop-slash-community-event-space of my fantasies?
And, more pedestrian:
Why not send a LinkedIn DM to a CMO Iāve long admired from afar?
Why not have coffee with a friend of a friend looking for career guidance?
Why not make the call, hit send, buy the domain, host the event, throw my hat in the ring?
As a recovering perfectionist whoās made my bed every morning of my life and color-coded the bookshelves in my home office, scribbling outside the career lines like this isnāt my first instinct and isnāt the most comfortable.
But itās also kind of exhilarating?!
Itās like when youāre stuck outside in a freak rainstorm without an umbrella and a long walk ahead. You can either hunker down under an awning for a while, or just lean all the way into the situation and take your time trudging through the rain, accepting youāre getting drenched and letting it be. Youāll dry off and warm up at your destination.
Itās not hopelessness, or foolhardiness, or denial.
Itās knowing that you donāt control the weather, so you may as well carry on. Itās optimistic acceptance.
Itās why-not-ness.
Have a great week,
Allison
P.S. If youāre interested in exploring what could happen if you let a little why-not-ness into your work life, come join me at my first in-person event: The Creativity of Workshop: Create Your 2027 Career Vision, Friday 10/2, 9-10AM in Philly. Itās a one-hour, small-group session for getting frank about what you actually want professionally, and setting up 2027 to go get it. Weāll use music as a tool to spark fresh thinking (no musical experience required). Limited to 20 seats. Get your ticket here.
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Really relate to this craving as an elder millennial trying to figure out my own next steps! Love the idea of adding "why not" as a frame for thinking about this. Thank you for sharing!