🥁 On Building More “Why-Not-Ness” Into Your Work Life

I’m Allison Stadd, drummer turned CMO, and I write for people who want to put the crackle back in their careers ⚡

This issue’s soundtrack:

Everything about my work life has been logical.

I’ve made color-coded spreadsheets to help me navigate job searches.

I’ve consulted mentors and recruiter friends before making any job change to ensure it would make my resume more compelling or minimally do no harm.

I’ve painstakingly shaped every sentence on my LinkedIn page.

I’ve catalogued career wins and learning experiences and honed them into well-worn stories to proffer in interviews and networking conversations.

When I’ve made career decisions based on heart or gut, it’s been with the clean framework “head-heart-gut-wallet” a colleague early on gave me; i.e. even when navigating by feel, it’s been formula-ized feel.

And all that logic and careful planning has served me well.

I’m proud of what I’ve accomplished over the last two decades, and I credit intentionality with a lot of that achievement.

Even when I’ve felt urgency or impatience around getting out of a gig and into a new one, I’ve resisted flailing.

I haven’t made professional impulse decisions.

I’ve 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 we’re talking about earning money and securing health insurance for our families, there’s limited bandwidth for whimsy.

In Janel Abrahami’s 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 I’ve used for the last nearly 20 years.

I’m craving more unexpectedness, more freedom and flexibility, more surprises; yearning for more “why-not-ness.”

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 I’d “finished” the full-time corporate portion of my career and could, I guess, luxuriate into a retirement of writing and small business management (?!).

But why couldn’t 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 I’ve 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 who’s made my bed every morning of my life and color-coded the bookshelves in my home office, scribbling outside the career lines like this isn’t my first instinct and isn’t the most comfortable.

But it’s also kind of exhilarating?!

It’s like when you’re 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 you’re getting drenched and letting it be. You’ll dry off and warm up at your destination.

It’s not hopelessness, or foolhardiness, or denial.

It’s knowing that you don’t control the weather, so you may as well carry on. It’s optimistic acceptance.

It’s why-not-ness.

Have a great week,

Allison

P.S. If you’re 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. It’s a one-hour, small-group session for getting frank about what you actually want professionally, and setting up 2027 to go get it. We’ll use music as a tool to spark fresh thinking (no musical experience required). Limited to 20 seats. Get your ticket here.

Folks across 42 U.S. states and 73 countries from companies like LVMH, Unilever, Salesforce, The Atlantic, and The Home Depot are reading along. You in?

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