It’s September. I’m drinking coffee on the balcony of my Los Angeles apartment. It’s been a few weeks since I got back from spending a summer on the East Coast.
On paper and on my Instagram, it looked like a perfect vacation. In practice, I spent a chunk of it figuring out how an S-Corp works and what it would actually mean for my taxes.
This year I finally stopped calling my side hustles “side hustles” and started treating them as a real fractional job. I wasn’t looking for a portfolio career. I had to create one out of necessity. So how did I end up here?
Welcome back to Retrospect, where I reflect on my nonlinear life and career journey, connecting the dots looking backward and drawing conclusions looking forward.
I split my life (and career) into pre-COVID and post-COVID time. I clearly remember when it was mandatory to be in the office five days a week, and when coming in sick was almost celebrated. “Look at you, you’re such a hard worker, you’re sick, and you still showed up.” Anyone else remember that?
Now it’s 2026, and we work remote, hybrid, and fractional. We have AI-powered businesses and automate as much as we can, trying to stay current so that we don’t fall behind.
I have always worked for startups, and I have always had an entrepreneurial mindset, which mostly meant fast-moving companies where the hours were never nine to five. I liked the speed, the mess, and building something with a small team. But someone above me always ran the business, and my paycheck was always guaranteed.
Consulting started as a side hustle. I never pitched for it. Opportunities came my way through people I’d worked with in the past, while I still had my W2. Small retainers, advisory hours, brand strategy, marketing ops, and some business development.
Then I left my full-time job last December, and everything went upside down.
I picked up more consulting hours while I looked for a full-time role. Then I noticed there were fewer full-time marketing roles to find, while fractional ones seemed to be picking up. I don’t think that shift is temporary. But that argument deserves its own piece, and I’ll cover it in my next story.
So there you have it. I leaned into fractional consulting and turned myself into a business. And becoming the business sounds a lot better than it actually is at first.
I learned the difference between paying myself a salary and taking an owner’s draw, and that the split between them is a decision with consequences, not a preference. I learned which expenses are truly deductible, which ones I simply wanted to be deductible, and what the IRS might ask me to prove. I built a reimbursement system, which is a strange thing to build when the person being reimbursed is also me.
Owning my own P&L feels very different from building the P&L slide in somebody else’s board deck.
I invoice now. I also follow up on invoices. There’s a very particular feeling attached to chasing a payment, and it’s not one I ever had as a W2 employee.
Then there are the timelines.
In May, I had a high-paying client about to sign a large retainer for a branding project. Then they ran into production issues and put the whole thing on hold, with no date attached. Not canceled, just paused indefinitely, which is somehow harder to plan around than a no.
At the same time, my workload at the branding agency I consult for doubled, and I found myself managing several brands under the retainer side of the business.
One door closed with no timeline on it, and another opened wider than I expected.
To make fractional work work, you have to get very good at sitting with uncertainty and very fast at pivoting. That’s the part nobody really talks about.
A potential client goes quiet for two weeks, and you have no idea whether that’s a vacation or a problem. A project that was supposed to start in June starts in August because priorities shifted. This is just how it works.
But when you are the business, every one of those shifts hits your calendar and your cash flow at the same time, and you’re the only one who feels it.
This is the part that takes more mental strength than I expected.
As a W2 employee, I always had a paycheck that showed up twice a month. Regardless of whether the quarter was good. Regardless of whether anyone liked my strategy deck. Regardless of whether I was sick, or on PTO, or sitting in a meeting that should have been an email. Somebody else was absorbing the uncertainty, and I never had to look at it. That was the arrangement, and it was a good one. Now I’m the one absorbing all of it.
But there is a certain beauty in all of it, which brings me back to my summer. You get freedom of time and location.
My clients don’t pay me for my hours. They pay me for outcomes. Nobody is checking whether I’m at my desk. There’s a joke that when you’re an entrepreneur, vacation just means working from a nicer location. It’s true. I’ve been on a train to the Hamptons with my laptop open on my knees several times.
I front-loaded work as much as I could so I could take some days off. Some days I worked until 11 p.m., and other days I closed my laptop at noon after my last client call. I went to conferences. Networked, planted seeds I hope will grow into friends and clients.
That’s the real difference between fractional consulting and a full-time job.
Your scope is defined, but your time is not.
I spent my free time intentionally: rebuilding my website (check out alicova.com) and turning Retrospect into the publication I always wanted it to be. Strategic, intentional content for ambitious people building nonlinear lives outside the traditional blueprint, covering entrepreneurship, portfolio careers, and personal reinventions.
Now that I’ve been brutally honest about the hard parts of fractional consulting, here is the great part I genuinely did not see coming. This year I have worked with more brands, across more categories and stages, than I would have in three years working for one brand internally. I learned things I would never have learned in-house, and not only about marketing, but about how other businesses are run.
So I’ll say the thing I don’t see said often enough around here. Building a portfolio career is harder than getting a full-time job.
Not harder in the sense of the work itself. Harder in the sense that all of it is yours at the same time: the delivery, the pipeline, the admin, the taxes, the uncertainty, and the part where you have to be your own manager on a day when you don’t feel like managing anybody.
Anyone telling you this is the easier path is selling you a dream.
I should be honest about something. I haven’t closed the door on going back in-house. If the right role came along, I would look at it seriously.
I haven’t made a decision. What I am committed to is exploring the possibilities and writing about them here, to make sense of what a portfolio career can be and how the job market is changing. So I don’t know yet whether what I built this year is freedom, or whether it’s instability that I’ve gotten good at describing. Some weeks it’s obviously the first. Some weeks I’m sitting on my couch applying for a Head of Brand Marketing job at 9 p.m. because I still don’t know if this path is right for me.
I believe entrepreneurship is the ultimate commitment. I’ve also come to realize it’s the ultimate freedom.
Nobody approves your time off anymore, but nobody guarantees your paycheck either. Same coin, both sides.
Next in Working Hours, I’ll dig into whether full-time marketing jobs are still a thing, and what building a portfolio career actually looks like.
If any of this sounds familiar, subscribe to Retrospect for candid conversations about entrepreneurship, portfolio careers, personal reinventions, and all the other paths that don’t fit neatly on a traditional résumé. Or forward it to the one person you thought of while you were reading.
And before I wrap up, as always, here are the two things I consistently used this summer and that are Worth the Shelf Space.
Ogee Improved Crystal Contour Collection
Ogee makes the best foundation I’ve ever tried, and their contour sticks are just as good. They recently reformulated the Crystal Contour Collection, and the new creamy version blends seamlessly and gives you a sun-kissed look that survives a humid East Coast afternoon. These three live in my makeup bag permanently. Everything they make is 100% natural, 83% organic, and skincare first, makeup second. Ogee gave me a personal code for readers: use ALIONA-OGEE for 15% off.
Hanacure Regimen
I’ve been a fan of this All-in-One Facial Mask ever since Drew Barrymore posted that viral selfie of her face looking wrinkled and granny-like while the mask dried. It’s a facelift in a bottle. I use it every couple of weeks for fresh, tight skin, and I brought a few pods east with me this summer because they are so easy to travel with.
In retrospect, the dots connect.
See you next time,
👏👏👏