🔌 A plot twist...

Winks from the universe and what's next for this season of my career

I posted this Note last week with zero context… and then immediately started second-guessing myself.

What if it was misleading? A contract could be anything: a house, a new client, a book deal… Wait—what if people think my big dream came true and that I got an actual book deal?!?

So let’s start by addressing the elephant in the room: I did not, in fact, get a book deal… at least, not yet. (Gotta finish writing the thing first…)

But, I did have a whirlwind of a week—the kind where life circumstances just magically seemed to snap into alignment. It felt like what Alex—whose Substack The Messy Middle I’m absolutely loving—calls a “wink from the universe.”

Needless to say, this Note of hers struck a major chord this week:

If I’m honest, I’ve been at a bit of a career crossroads lately, quietly trying to figure out my next steps.

I adore working on my book (and this Substack!) and am beyond grateful to my husband for supporting my dreams and encouraging me to write for the past two(ish) years. And I’m also self-conscious about the fact that I’m still not finished with the first draft, despite having ample time to focus on it. (Two things can be true!)

It’s hard to shake the nagging inner critic that whispers, You should be done by now. Whenever my thinking wanders in that direction, I try to remind myself that there’s no one-size-fits-all way to write a book: we each move at a different pace, slow progress isn’t failure, this isn’t a race, we can’t force creativity or treat it like a KPI.

Somewhere deep down, I imagined I’d finish a first draft before dipping a toe back into additional work, whether that was an in-house role or independent/fractional/freelance work. But over the past month or so, I’ve realized that may not be the case, and I began thinking about what’s next.

I’ve been unsure about what that path looks like—but here’s what I do know:

• I gravitate toward the idea of a portfolio career—though I’m not 100% certain what that looks like for me at this moment.

• I don’t want to be in-house full-time at an early-stage startup in a senior-level role right now. That level of pressure and responsibility doesn’t call to me at all.

• I want to move away from strictly social media—something I’m 99% sure I’ve said since I first started in social media. I’ve broadened my skillset over the past five years and don’t want to take on a purely social role just because it’s familiar.

• I don’t want to apply for in-house writer roles or be a freelance writer—the kind of writing I want to do is specific to my own creative projects and endeavors. (Exception: comms/brand-related roles that involve writing, but aren’t specifically for marketing copy.)

• I’m less precious about titles and more precious about boundaries. My goal is to earn a meaningful income in a way that aligns with my nervous system and still allows me to focus on the “life” part of my pie—and to continue writing my book.

This season of my career

With a rough sense of my goals, I turned to Mary Jantsch (obvi) and her wonderful Career Season Finder to help me figure out what I need most right now.

Results from Mary’s Career Season Finder

(PSA: This tool is free to try, but Mary also works with folks 1:1 who are craving a deeper dive!)

My career season results were spot-on. Pulled from What Season of Work Are You In?:

Spring 🌱

Spring feels like the return of curiosity after a long stretch of quiet. You’re not totally clear on what’s next, but you want to explore. It might show up as bursts of energy, random ideas, or the urge to say “yes” to things that aren’t fully logical yet. There’s this sense of possibility again, and that in itself feels like momentum.

What helps: giving yourself permission to try things without committing to them. Light structure. New inputs. Being around people or ideas that spark something.

What strains: pressure to have a fully formed plan. Deadlines. Treating it like you need to be “back” already. That shuts down the experimentation before it even has a chance to take root.

The biggest blocker I was still struggling to wrap my head around: whether I wanted to go the freelance/fractional route or be back in-house somewhere.

Over the past two years, I’ve devoured fantastic Substack essays on the death of the corporate job, the Great Millennial Career Crisis, and the rise of the fractional economy. I’ve spent hours upon hours thinking about the future of work, finding myself pulled toward those who are imagining (and forging!) a new era of career growth: webs, not ladders; gardens and seasons, not lifelong decisions. I’m endlessly curious about career crossroads and inflection points, and the building of portfolio careers that skew toward freelance opportunities.

I can’t stop thinking about Iwana Johannsen’s piece in Afterwork on how to feel safe without a job:

Years ago, my husband told me he didn’t understand why people would consider employment safer than entrepreneurship. He said “I feel safe because I know that I can create opportunities myself and make them a reality without depending on the job market.”

Do I consider employment safer than entrepreneurship? Are both equally unstable right now, especially against this rapidly evolving AI backdrop? And if so, does going back in-house feel like a cop-out? Does it look like I’ve been preaching one thing and practicing another? (Do I even care what it looks like?! Or just what it feels like? *cough cough, New Year’s resolution.*)

I keep coming back to some advice that a mentor-turned-friend (shoutout to Sam Lee) gave me a few years ago, when I was first freelancing: you can think about in-house and independent work as swim lanes you can get in and out of at any time—there’s no pressure to stick to one lane.

The more I think of my career as an expansive playground for trial and error, curiosity, and experimentation, the less pressure I feel. Like Hannah Zhang (Nonlinear News) puts it: “I stopped asking, ‘what should I do with my life?’ and started asking, ‘what do I want to try next?’”

Between nudges like Hannah’s, Sam’s advice, and Mary Jantsch’s fantastic piece on moving between multiple ways of working—the closest someone’s come to articulating exactly how I feel!—I realized I had my answer. Instead of being so black-and-white about what’s next, I could get creative.

Mary sums it up like this:

The pressure to “pick one” [way of working] comes from both outdated cultural models and the optionality model’s demand for legibility.

The goal isn’t to “just pick one”…

The goal is to accept that moving between ways of working *is* a model. Contained iteration *is* a model.

And that’s when the universe kicked in.

Winks from the universe

As if in response to my specific ask, the universe winked at me in quick succession. (Maybe it had something stuck in its eye. Or maybe it needed help and was giving me the secret signal. Hard to say.)

Within a few weeks, I had three potential opportunities lined up. Mentally, I couldn’t help but envision them side by side, like doors on a game show that I got to choose from. (But more whimsical and with recharge brand colors, of course…)

Here’s how it all unfolded—and which door I’m choosing.

Literally how my mind felt last week 💫

NOTE: I realize I’m positioning these all as the result of pure luck—but behind the scenes, there were years of hard work and relationship-building that went into this outcome and provided the scaffold for these opportunities. I don’t mean to suggest you just make a vision board and snap your fingers and ✨tada!✨ (Though honestly, that may work, too… who am I to say?)

Earlier in March…

🚪Door #1: A freelance contract

A few weeks ago, a former freelance client of mine from 2021 emailed me out of the blue, curious if I’d be open to a 3-month social media contract. Initially, I hesitated because in my heart of hearts, I desperately want to move away from social media as my specialty. (She says on Substack…)

Right on the heels of that email, I got two different texts from former colleagues asking if I was taking on freelance social media clients. Felt like a big wink… but maybe also a test.

🚪Door #2: A mat leave cover

Around the same time I heard from door #1, I got a DM from a current freelance client saying she was going out on maternity leave starting in April and was looking for someone to cover for her for six months. I offered to share the JD with my network, and also voiced interest in throwing my hat in the ring. (Based on her feedback, it seemed like I might not be the right fit for what they were looking for, so I assumed it was a no-go, but still. Don’t ask, don’t get!)

🚪Door #3: An in-house role

I saw someone in my LinkedIn network whom I trust and respect post about a customer stories role on the marketing team at her company—not a title I’ve held before, but the job description sounded like it was up my alley, and I was impressed by the company’s values and trust-first (remote) culture. Even though it was a little bit of a stretch, I decided to apply. When I didn’t hear back after two weeks, I figured that was also a no. (Maybe the universe was telling me it didn’t want me going back in-house full-time! Was that another wink?!)

Fast forward to last week…

🚪Door #1: A freelance contract

I emailed my former client back to get more information and continue the conversation—but by the time we spoke, the ask had changed… to be even more in line with what I’m looking for. Instead of social, she wanted support in shaping the brand’s narrative arc and communications messaging as they develop new product lines and map out their B2B storytelling to reach more people. Their budget was decent, so if I took that on in addition to two other clients, it’d work well.

🚪Door #2: A mat leave cover

I unexpectedly heard back from my freelance client, saying she’d love to chat about the possibility of me covering for her. It’d mean stepping into a full-time role from April through October—but then I learned they’re comfortable with 35 hours per week instead of 40, meaning I could use those extra 5 hours (and then some, of course) to keep working on my book. (Bonus #2: It turns out the role reports to someone I’ve followed and looked up to on social media for ages; I didn’t even realize she was at the company! The chance to learn from and work with her would be HUGE.)

🚪Door #3: An in-house role

I heard from the recruiter shortly after I told myself I’d been ghosted. (Reminder that it’s not your job to count yourself out!) We had a really lovely conversation, and I had a strong feeling that it could be a good fit—especially since they were looking to bring someone on within the next two weeks. The recruiter moved me through the interview process on the spot (God bless her!) and set up a time for me to speak with the hiring manager later in the week.

So, what did I decide?

First of all, I decided I’m not picking one lane permanently. Nothing is a forever decision.

But for now, I’m choosing door #2—a content strategist role on the brand narrative team at a larger public company (aka not a series A startup!).

I’m treating this as an experiment—a six-month trial to see how it feels to be back in-house during this season of my life, without the weight of growth marketing KPIs on my shoulders. To test the waters. To try a new reporting structure, learning directly from someone I trust.

Instead of calling this journey “the next chapter,” I’m thinking of it as a natural evolution—a way to play with the idea of a “9-to-5 job” as part of my broader portfolio career—not the biggest piece of the pie. (Channeling mallory contois for inspo—I love how she does this with her VP of Growth role at Maven!)

My hope is that a fixed-term contract covering for someone else helps me separate my work from my identity. Yes, I want to do good work, make an impact, and deliver high-quality results, but I don’t want to sacrifice my nervous system to do it.

As Max Pete put it in his recharge feature:

I realized that the tech dream often requires you to sacrifice your nervous system for the sake of scale… Eventually, I had to step back and ask myself what I was actually working toward… no amount of stock options or prestige was worth the way I was feeling.

Things I’m reminding myself

I’m super grateful that this “job search” process (if we can call it that) was relatively straightforward and quick, especially in a wild job market. But amidst the gratitude, other feelings are swirling, too: anticipation, nervousness, discomfort.

Candidly, I’m worried about falling back into old patterns and habits: checking Slack first thing in the morning, being glued to my phone at all times and therefore available 24/7, skipping lunch because I’m “too busy,” working late into the night, the whole shebang. I’m worried about defaulting to “performing my way out of my uncertainty,” as Emma Pan so beautifully wrote in this essay. And I’m worried about whether my anxiety and impostor syndrome will resurface the way they did at Teal.

Here are a few things I’m reminding myself to help temper that worry. (Sharing in case some resonate with you, too.)

• My career has had a funny way of unfolding exactly as it should—at least in hindsight. I want (and need) to believe that this opportunity is part of that tapestry, and to continue to rebuild trust in myself, my judgment, and my decision-making.

• It always comes down to the people—and in this case, I’d be covering for someone I know, trust, and respect, AND reporting into someone I’ve looked up to and followed on social media for years. The chance to learn from and work with her is amazing, regardless of the outcome.

• This role is different than my last role. Different team structure (IC vs. manager), different boss, different product, different goals, different everything. The question of whether I’ll burn out again is real—but I’m consciously changing the variables that I think had the biggest impact.

• Speaking of the variables I can actually control: My own behavior and my boundaries. As Simran Sidhu reminded us in a recent Q&A:

  And be honest—what if it’s actually you? Did you really need to be working all those evenings? Are you on Slack when you don’t really need to be on?

• I’ve done so much work over the past two years—some of it visible, some of it not—to regulate my nervous system, come back to center, and repair my relationship with work as a whole. I’m approaching this opportunity with a fresh perspective and learnings from therapy that can help along the way.

• Worst comes to worst, I can always leave. The door isn’t locked. And I’ve gotten better at more quickly identifying what doesn’t work for me.

• My burnout wasn’t a “me” problem; it was a systemic problem. And maybe I was in the wrong room, “chasing recognition that was never designed to be forced,” as Alexandra Cole suggests.

Things I’m working toward

A few goals I’m setting for myself as I head into this new role:

• To lean into trusting myself first.

• To keep thinking of this contract as part of my portfolio career—just a piece of my life pie, not the whole thing.

• To stick to my boundaries and not work on the weekends (unless something’s absolutely dire).

• To fully log off at night to be present with Ben and Waffles—no Slack notifications after-hours, no compulsive post-dinner work sessions, no worrying about whether what I did that day was “enough.”

• To prioritize my well-being over my work (e.g., drinking enough water throughout the day, keeping my scheduled workout classes, eating lunch away from my computer every day).

• To establish healthy habits right out the gate: not checking my phone first thing in the morning or sitting down at my laptop in my PJs for “just one quick thing” or volunteering to hop on calls at ungodly hours to appear flexible.

• To continue to prioritize writing. I’m determined to finish my book and committed to keeping up with the recharge, even if the publishing cadence may look a little different.

If you’ve read this far (or even if you’ve scrolled ahead), thank you from the bottom of my heart. For being here. For reading. For supporting my creative endeavors. For making me feel less alone as I navigate this chapter.

I’m excited for what’s to come, and grateful to you for being a part of it.

🔌 2025, unwrapped

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