Though my gut reaction was a firm NO, I obliged and started posting ChatGPT-composed content (but not before some heavy-handed editing).

Only in hindsight do I understand I wasn’t simply resisting AI. I was resisting what AI represented in that moment: a shortcut to producing output for the sake of more, not better — strategy be damned.

Fast forward about a year and a half: today, I’m self-employed and working with five clients. I use Claude multiple times a day, every day. I attended Grace Clarke’s class, AI for Normal People. I downloaded Cowork and have been discovering new use cases every week.

My adoption has been partly driven by anxiety — as a marketer, I don’t have the privilege of opting out — and by selfishness: I want to be more efficient now that I’m in full control of my time.

I’ve also become nosy about how other marketers are using these tools. Obviously, I want to understand how my adoption stacks up. Maybe less obviously, I want someone to give me the answers; to show me a use case I’ve never thought of that will change my life. It hasn’t happened yet, but I’ll let you know if it does. (I’m not above the human urge to seek shortcuts.)

A few weeks ago, my curiosity led me to create a survey on how marketers are using AI. The majority of respondents were self-employed, and I noticed an interesting split between their opinions on AI and those in full-time jobs. Adopting AI because your boss mandated it is a completely different energy than choosing it yourself.

Now for the survey results.

Freelancers are more excited and less conflicted about AI than full-timers.

61% of freelancers feel excited about AI, compared to 50% of full-timers. That might be because freelancers are choosing to adopt the technology (45% say they experience no external pressure), while 75% of full-timers report experiencing moderate to heavy pressure from leadership.

Recently, a friend told me her CEO essentially “instilled the fear of god” in his employees — that if they don’t adapt, they’ll be pushed out. I’m not sure that’s an effective motivation tactic, but what do I know?

Subscribe now

Full-timers are significantly more worried about job elimination.

28% of full-time respondents expect AI to eliminate a significant number of marketing roles. Only 12% of freelancers said the same. And 29% of freelancers think the changes will be mostly positive, compared with just 14% of full-timers. It seems like marketers in“stable” 9-5 jobs are more worried about how technology will reshape their industry.

But AI is changing scopes and rates for freelancers.

One freelance copywriter shared, “I’ve gone from charging 2 weeks’ worth of work for a white paper to being expected to write it in 2 days.”

Another wrote, “I'm concerned about the perception of how long things take with AI. I've generally moved away from charging hourly, but I'm following consultants in lots of disciplines to see how they navigate this charging for time vs. value conversation that AI is distorting."

I’m right there with them. I’m trying to move away from hourly billing because AI has made me more efficient. That said, I’m still delivering the same, if not greater value. I’ll report back on this endeavor later when I have learnings to share.

AI is what allows freelancers to operate as a “team of one.”

Freelancers are using AI to fill roles they don’t want to, or can’t, hire for: a statistician, a developer, a research team, a compliance checker. One person is running statistical analyses they used to pay a specialist for. Another built a social metrics dashboard to replace SaaS subscriptions. Someone else built outreach agents because they have no sales team. One respondent put it best: she’s training agents to act as her ‘faux team.’

How I’m using AI in my day-to-day work

Now I’m going to tell you exactly how I’ve been using Claude and Cowork to support my client work. Though I’m a true generalist, I now focus on three specific areas of marketing: email/retention, brand strategy, and brand marketing.

I hope this goes without saying, but I never share anything Claude produces for me without first reading and validating it. I almost treat it like a fresh-out-of-college employee — I know I need to give it super clear instructions, and I always check its work.

Below, I’m sharing 12 ways I use Claude and Cowork in my day-to-day for paid subs. I think this will be most useful to anyone who works in the same areas I do: email, brand strategy, and brand marketing.

Read more

I’m immensely grateful for the experience because it helped me ease into full-time freelancing, but I don’t think I’d take the same role again today.

My first mistake: I did zero research on fractional gigs before I signed my contract. Once I started making freelance friends, I heard stories similar to my own: that these opportunities often felt more like full-time positions with no boundaries or benefits. I was relieved I wasn’t alone, but frustrated wit11h myself. I would have done things differently had I sought out more information first.

So I asked five other marketers (six if you include me) what their fractional roles were supposed to be, and what they turned into.

Ok fine, I’ll go first.

When you took the role, what were you told it would be (hours, scope, expectations), and what did it turn into?

The scope was as broad as you would expect for a full-time Head of Marketing hire. I knew they had two people on the internal team and a few agencies, so I assumed I’d be doing more strategy work and oversight rather than hands-on execution, given that I was contracted for 30 hours. In reality, most of my time was spent on execution, largely due to the company’s way of operating and the stage of the business. I never pushed back on the work I was doing because the scope was so expansive (and ultimately, I’ll do whatever’s needed of me), but it did force me to set and hold boundaries around time and responsiveness.

If you had another opportunity to take a fractional head of marketing role, would you? If no, why? If yes, why and what would you do differently this time?

I would not, but I would (and have) taken more defined fractional roles like “head of brand” and “head of retention,” which I love. The reason is two-fold: I enjoy some areas of marketing more than others, and I believe in diversifying my income as much as possible. That means I now split my time across 4-5 different clients depending on the month, and I wouldn’t want to give so much of my week to one business.

Knowing what you know now, what would you tell someone who’s about to sign a fractional contract that sounds really appealing on paper?

Make sure your scope and time commitment are clearly defined in the contract, and have any necessary conversations upfront to get there. Often, I think this means slowing down the process to get to know the founders and team.

I’d also check my own energy and intentions. I really wanted this last fractional role, so I kind of just bulldozed ahead and heard what I wanted to hear. That’s not normally how I approach conversations with potential clients. I really only want to work with someone if it feels like a fit on both sides, and, to be honest with myself, that’s not how I approached this last fractional role. It shows.

Subscribe now

When you took the role, what were you told it would be, and what did it turn into?

My first fractional role was with a company so early in its launch that the scope was intentionally drafted loosely so I could have the autonomy to build. Although I had agreed to 30 hours per week, the amount of work needed to architect the marketing function far exceeded both my expectations and the brand’s. Most early-stage brands (I’m talking pre-series A) don’t realize what it takes to actually market the product. I’m not just talking about the creative investment, but the tech stack, customer auditing, and baseline strategy work to establish product-market fit. With most of these brands, a fractional Head of Marketing is handling both the build and strategy, as well as execution and world-building. One person is responsible for the output of five different core marketing & creative roles.

If you had another opportunity to take a fractional head of marketing role, would you? If no, why? If yes, why and what would you do differently this time?

Yes, but with a caveat. It comes down to drafting a scope so the client is clear on what they can expect from a fractional Head of Marketing. We’re not marketing departments. I’ve started to narrow my offering to a specific niche in the marketing funnel, and when a client asks for more, I clearly outline what that investment looks like. It goes back to a lack of understanding around what we do and what it takes to scale a brand through marketing — they don’t know what they don’t know.

Knowing what you know now, what would you tell someone who’s about to sign a fractional contract that sounds really appealing on paper?

Protect your peace. It’s okay to be passionate about the work and go beyond the scope when necessary, but remember that you’re building your own business as well. The best part of being fractional is having the autonomy and flexibility to work with who you want, when you want. I say this because a big fractional role might look amazing on paper, but once you get into it, it might be all-consuming — even more demanding than when you were on the corporate side. For me, that’s a big red flag and exactly what I left the corporate side to avoid.

When you took the role, what were you told it would be, and what did it turn into?

In my case, I was the one who pitched the idea of coming on as a fractional head of brand after completing a 6-week verbal brand identity project. And I did this for two clients at the same time. I reserved 15 hours a week to support each with strategic copywriting and marketing work, and realized slowly over the course of a year that I’d overextended myself. I spent all my time on my clients’ businesses, and none on my own, which meant I basically replaced my full-time role with two fractional roles (without receiving any benefits—healthcare, 401K, etc.) and fully neglected priming my pipeline.

If you had another opportunity to take a fractional head of marketing role, would you? If no, why? If yes, why and what would you do differently this time?

No, but I wouldn’t necessarily advise other consultants against it. Some of the greatest lessons of entrepreneurship come from trying things on and seeing what works (and what doesn’t) for you. I realized that I wanted to operate more independently, which also meant giving up a certain level of security (recurring monthly income), and I needed time to prepare for that next step. Also, working styles differ—what doesn’t work for me might be someone else’s dream gig. I know several consultants who thrive in fractional roles that require a significant portion of their weekly hours and allow them to become deeply embedded in the work for several months at a time. If that style of work works for you, more power to you!

Knowing what you know now, what would you tell someone who’s about to sign a fractional contract that sounds really appealing on paper?

Most often, with these types of fractional roles, the brand leaders or founder(s) are going to expect they can get in touch with you when they need to. It wasn’t uncommon for me to receive texts and phone calls from the founders I supported throughout the week, which meant stepping away from dinner or chatting with them as I went for an afternoon walk. Know that that’s what you might be signing up for, and decide if you’re up for it. Clearly outline your scope (enforcing boundaries is the most important soft skill for consultants!), but also: prepare to be flexible (and on call).

Subscribe now

When you took the role, what were you told it would be and what did it turn into?

On paper, it was a clean fractional role. About 15 to 20 hours a week, focused on strategy, leadership, and setting the roadmap. It was framed as, “We have a team, we need a strategic partner.” In reality, it expanded pretty quickly — execution, troubleshooting, and filling in gaps. It’s hard to stay “fractional” when things are moving fast or the team is still taking shape.

Would you take another fractional Head of Marketing role? What would you do differently?

I would, but I’d be a lot more clear going in. Fractional works when a company really knows what it needs. It gets messy when it becomes a catch-all for “we need senior strategy, execution, and also can you just figure everything out?” Next time, I’d lock the scope earlier, and I’d look closely at the team. Fractional only works if there are people in place to carry things forward. Otherwise, you quietly become full-time with a part-time title, which is a fun surprise for no one.

What would you tell someone about to sign a very appealing fractional contract?

If it looks perfect on paper, read it again. Push on scope, support, and decision-making. What are you responsible for versus advising on? Who is actually doing the work? And can you make calls, or are you politely suggesting things into the void? Also, sanity check the hours against the ambition. Big growth goals and new channels are not a 10-hour-a-week situation, no matter how optimistic everyone feels at kickoff. And pay attention to how they talk about marketing. If it sounds like they’re hoping you’ll come in and fix everything quickly, that’s usually your answer. Fractional can be great. It just stops being fractional the second no one is watching the edges.

When you took the role, what were you told it would be (hours, scope, expectations), and what did it turn into?

I’ve had maybe 8 long-term fractional roles over the last 10 years of freelancing. Some have been totally chill, especially when the company knows little about creative and marketing and I’m truly leading the charge. But some are just JOBS. And even if I’m scoped for only 20 hours a week, the first person to violate my boundaries is always me.

Sometimes I’m overgiving. Sometimes, there’s just stuff that needs to get done. But it’s honestly hard to jump into a fractional role: be on the team, in meetings, on Slack, and not just get so carried away “doing your job” that you forget about the boundaries of your scope, meaning agreed-upon deliverables, hours, all of it. Especially if you’re a can-do, multi-hyphenate problem solver. Which I am.

If you had another opportunity to take a fractional head of marketing role, would you? If no, why? If yes, why and what would you do differently this time?

Fractional roles have built my portfolio and given me great, consistent income. The one role I won’t take on again, though, is Fractional CMO. As a C-suite contributor, you need to be invested in the business’s bottom line. And the truth is, I’m happy to strategize, advise, even execute. But I don’t want to take the work home with me, and that’s what CMO work felt like: major stress about whether the company was succeeding or not. Yes, I hope my work contributes to a company’s success, and I’ve seen it drive big results for clients. That’s why I’m always booked and busy. But there is a different level of pressure that comes when the success is riding on your back.

Knowing what you know now, what would you tell someone who’s about to sign a fractional contract that sounds really appealing on paper?

Scope on hours rather than deliverables. That way, your fractional role won’t take over your entire life. Don’t sign up for any roles that are more than 20 hours a week: that’s just a full-time job without benefits. Communicate clearly about what you’ll be able to accomplish in the hours you’re scoped for, and stop when you’ve used up your time for the week. If you’re constantly working overtime, speak up. Ask to rescope, or scope back entirely.

When you took the role, what were you told it would be (hours, scope, expectations), and what did it turn into?

The honest answer is that these days, I see this as partnering with prospective clients to shape an engagement rather than responding to their JD, so the gap between expectations and reality is much smaller. That said, my first true fractional engagement was kind of a mess, and a lot of it came down to unclear expectations on both sides — and being so eager to win the work that I didn’t really vet the client (more on that here). These days, I do a lot more vetting upfront and am much more deliberate about how I define the work before we put a contract in place.

If you had another opportunity to take a fractional head of marketing role, would you? If no, why? If yes, why and what would you do differently this time?

Yes — the majority of my work over the last five years has been fractional in nature, and I really enjoy it. I’ve shifted toward positioning myself as a fractional CMO rather than a fractional “head of,” which better reflects my experience, my rates, and the kind of scope I want to own. I’ve found that the title helps set expectations and signal the level of the relationship from the start.

Knowing what you know now, what would you tell someone who’s about to sign a fractional contract that sounds really appealing on paper?

Don’t be afraid to negotiate, and set expectations early — before you sign a contract. That includes not only scope, but also things like payment terms, decision-making authority, and how you’ll show up day-to-day. The engagements that go sideways usually had warning signs before and during contract negotiations that felt too awkward to address. Address them anyway.

I wish I’d known everything in the answers above a year ago, but alas. If you’re in talks for a potential fractional role that sounds too good to be true, do what I didn’t: do the research, ask the awkward questions, and assume the scope will grow. If this was at all useful, pass it along to a self-employed marketing friend.

I remember exactly when the bubble burst. Later that day, I called my boyfriend, crying into the phone as I sulked down Myrtle Ave on the final leg of my commute back to Brooklyn.

When shit gets hard, my natural instinct is to flee. My learned instinct is to fight.

In bed that night, my teary frustration hardened into steely resolve as I cracked open The Obstacle Is The Way by Ryan Holiday. I knew I was in for a challenge, but I was determined to make it work. After all, a lifetime of ballet training and girlboss hustle culture taught me that suffering is just the price of success.

I rode my steadfast determination through the next 6 months. I checked Slack 24/7 and was responsive at all hours. I looked for creative solutions everywhere and said yes to ideas I knew wouldn’t work in service of team spirit. I met my directs with an attentive smile, even after my emotional resources hit empty.

Was I having a good time? No.

Was it working? Yes.

I fell into a rhythm that helped me manage my mounting exhaustion. I did the healthy things: therapy, journaling, working out. I started a meal delivery service for breakfast, lunch, and dinner to save time. I also did the unhealthy things. I numbed out by watching YouTube videos in bed at night. I shopped — a lot — as a way to enjoy the fruits of my labor.

I felt old, in an existential kind of way. I was participating in the infamous midlife tradition of emptying myself out for a career my lifestyle had grown dependent on. I was 33.

If my primary emotional experience was anxiety, my secondary emotional experience was a sick and twisted form of pride.

My brain concocted a self-congratulatory narrative, and my ego ate it right up. After all, this was my version of a Disney fairytale. Woman experiences hardship. Woman perseveres. Woman overcomes. Woman wins success and lifelong happiness. I’d been rehearsing this plot my entire life — from my ballet studio to my hustle-porn Instagram feed — and now it was my time to shine.

For a while, the storyline held. I basked in the spotlight of my own private hero’s journey.

But eventually, weekend by weekend, the boundary between my time and my work dissolved. I’d find myself glued to Slack while out at drinks on a Saturday night, and back at my laptop Sunday morning, hunched over my keyboard with a cup of coffee. Evidently, the spotlight had lost its thrill.

My brain started to perform new calculations. What was a fair trade for my cushy salary? My values had shifted in a way I hadn’t anticipated. I was willing to relinquish my time for professional success. I was surprised to learn I wasn’t willing to relinquish my autonomy.

Subscribe now

While this admission felt like dignity, I couldn’t ignore a slithery undercurrent of shame. Resilience had fed my self-esteem for so long. Who was I without it?

I was proud of myself for fighting, so fleeing felt like failure.

I wondered how the ambitious twenty-somethings on my team saw me. Did they think I was weak for abandoning my career goals? Younger me certainly would have. I can see her judging me with greedy disappointment, plotting how she might exploit my departure for her own gain.

My decision to leave was excruciatingly difficult, but ultimately, a more grounded form of self-worth won out over my ego. I had graduated from an old belief system.

I no longer believed I needed to suffer for success. For the first time, maybe ever, I felt worthy of ease.

I knew I could make the same money, if not more, while working on my own terms. (Yes, it feels audacious to say that out loud, and yes, I was right.)

I knew I’d feel happier if I could allocate more energy to parts of myself outside of work. (Can’t believe this took me 12 years to figure out.)

I still value the practice of resilience. But worshipping at its altar hasn’t served me well. Resilience is useful, but resilience in service of what?

This tension between fight or flight, resilience or release, is an ongoing negotiation within myself. It’s not binary. It shifts over time as my external circumstances and my internal compass evolve. It relies on a heavy dose of self-trust.

What are you enduring right now, and what exactly are you enduring it for?

I did do that. I have a marketing background. I could pull together a snappy list of best practices — post consistently, engage on Notes, find a niche, blah blah blah. And it wouldn’t be wrong, exactly, but it also wouldn’t be completely honest.

The truth is: I don’t actually know how I grew my audience on Substack.

I know that content about freelancing drives paid subscriptions. I know that posting on LinkedIn drives views. I’ve analyzed my newsletters, looked for patterns, and tried to reverse-engineer the wins. Sometimes it works; usually it doesn’t. Not because I’m not smart enough — I’ve worked in marketing for 12+ years — but because the mystery of life persists.

The part of me that wants to write that listicle is ego. I’d love to believe I figured something out, and that my modest success validates my intelligence. But who am I to believe I can bend the universe to my will?

The irony is that marketing is rooted in the belief that brands can, in fact, bend the universe to their will. We’re in the business of manufacturing outcomes.

Exited founders write a LinkedIn post about their “seven secrets to success.” Marketers craft frameworks and playbooks. VCs build pattern-matching systems to identify winners.

And yet roughly 90% of venture-backed startups fail. Sometimes it’s due to a lack of product-market fit or poor decision-making. But often, very smart leaders with good products, great teams, and enough funding can’t make success happen. Plenty of deserving people win and plenty of deserving people lose.

The problem with marketing is that it doesn’t account for luck. Often, marketing presents playbooks as deterministic: do X, get Y. But certain behaviors just make success more likely — nothing is guaranteed.

The industry sells certainty, agencies sell repeatable frameworks, and courses sell the promise of outcomes. All of us need to believe success is within our control, a puzzle we can solve with enough analysis and effort. Would admitting luck’s role undermine the entire expert economy?

That’s a scary thought.

If luck matters in business, success doesn’t fully validate us. If luck matters in business, failure doesn’t always give us clean lessons learned. If luck matters in business, we lose the comforting narrative of cause and effect.

We’d be forced to reckon with the uncomfortable truth that success doesn’t always make someone superior — just luckier.

As marketers, what do we do with this? Give up altogether?

I’d never tell you to burn your playbooks. Instead, I think we can approach marketing with more intuition and nuance:

Don’t over-rely on playbooks: Something that worked for another brand may not work for you. Following someone else’s “8 things” might just mean you’re optimizing for their luck, not creating your own.

Ask different questions and explore unconventional creative solutions: When you accept luck’s role, you actually become more creative rather than less disciplined. You’re freed from rigid adherence to what “should” work.

Utilize your gut instinct and intuition, not just data: Marketing is an art and a science. Data tells you what worked in the past under specific conditions, but it can’t predict the unpredictable breakout moment. That’s why decisions based solely on data don’t always yield the best results. Intuition might help you take risks that data would discourage, but that create the conditions for luck.

I try to bring this approach to my client work and to my personal projects. The growth-hacky Substack newsletter headlines always lure me in, but I never learn anything meaningful. Sure, certain practices have helped me build an audience, but taken together, those practices don’t tell the full story.

The role of luck in marketing is something that’s been pulling at me for a long time. I notice it when a founder asks me for a retention playbook, and when I feel the urge to write a newsletter about how I grew my audience. (I am both the offended and the offender.)

There’s nothing more human than the desire for control, but I find relief in naming the mystery. Acknowledging the role of luck in success doesn’t make us worse marketers — it just makes us more honest. And maybe that honesty is exactly what creates the conditions for more thoughtful work.

Intellectually, I’ve known I’m going to die from a young age, but I didn’t internalize it until last year. I’m 34.

I’m talking about this here, in a forum for career content, because I believe mortality drives more of our professional decision-making than we’re usually comfortable acknowledging.

Here’s a bit of context: About a year and a half ago, I started noticing some signs that I had officially become a Real Adult. My friends started having babies. I became an aunt. I was working a new job and making more money than I ever had. I moved in with my boyfriend. Check, check, check.

Simultaneously, I started to feel old in an existential kind of way. I was exhausted by work, had little energy for anything else, and worst of all, my days started to feel routine and lifeless.

Then, last September, an awareness of mortality hit me hard and fast: in the same week, my last living grandparent started chemotherapy, and my 13-year-old cat fell ill, spending three nights in treatment at an emergency vet.

I found myself thinking about death daily. A few weeks later, desperate for relief, I confessed those thoughts to my therapist.

There’s immense power in saying your scariest inner dialogue out loud, and once I did, I started to hear it everywhere.

Last month, three headlines slapped me in the face: “Feeling Old: 44 Is the First Big Aging Cliff for Millennials” for New York Magazine, This Is the Year Millennials Officially Got Old by the New York Times, and “Midcareer Anxiety Is Peaking. Millennial Women Are Recalibrating on Forbes.

Each story made me feel seen, but in a small surface-level way. Yes, I’m starting to feel old — physically, culturally, and professionally — but why does that feel so confronting? Something was missing from the narrative.

Subscribe now

I found my answer in a book recommendation from my therapist: Staring at the Sun by psychotherapist Irvin D. Yalom. He posits that the fear of death is the root cause of most human anxiety, writing “...the more unlived your life, the greater your death anxiety. The more you fail to experience your life fully, the more you will fear death.”

That was it. Yalom’s words immediately untangled my knotted fears about aging, feeling old, and being dissatisfied with work, all recurring themes for me in the last year. My career no longer provided the fulfillment and purpose it once did in my twenties. Instead, I felt it was preventing me from experiencing life the way I wanted — as an autonomous, ambitious person with a lot of interests.

I regularly talk to people about their careers, so I know I’m not alone. I began to notice that many struggle to articulate why they’re unfulfilled in their professional lives. It feels like there’s an underlying reckoning they can’t quite put into words, but I notice it in phrases like “everything feels so meaningless” and “I don’t know what the point is.”

Having experienced this reckoning myself, I think I know what they mean: “I’m aware that I’m aging. I’m running out of time to do the things I want to do. I can’t bear the thought of giving 40% of my remaining waking hours to a job that feels meaningless. What do I do?”

Subscribe now

Sometimes, I trick myself into believing that more time is the solution to my fears about death. It leaves me wistful for my twenties or running through scenarios about how many years I have left. But the more I’ve thought, talked, and read about mortality, the more I realize how silly I’m being. My fears about death aren’t assuaged by more time. We don’t get more time. It’s an impossible solution. (I’m not a fan of Bryan “Don’t Die” Johnson if you couldn’t already tell.)

My fears about mortality are only assuaged when I accept that my time is limited and act in accordance with that truth.

The passage of time is terrifying, but isn’t it also life’s greatest motivator? How would we operate if time were an unlimited resource?

If I had unlimited time, I’d probably sleepwalk through years of my career, collecting money and titles and achievements like a lab rat in a maze, hoping to one day beat the game and collect my prize of Lifetime Fulfillment.

Wait, I actually did do that.

It’s only in the last year that I’ve started to look my own transience in the eyes. Through it, I’ve found a gnawing motivation to live the way I actually want to. It ate away at me until I left the job, started freelancing, spent more time doing the things I love, and pursued interests I hadn’t had energy to acknowledge.

If you’re circling similar feelings about your career, a fear of death might be buried at the root of it. I know it feels easier to push the anxiety down — but if you keep ignoring it, you risk sleepwalking your life away.