Here are a few fun vanity metrics:

• 8% — How much more I’ve made, on average, each month while working less, with more control over my schedule

• 1,921 — The size of the subscriber base I’ve built on Substack

• 113,938 — The number of LinkedIn members my posts have reached

• 0 — Total work-related Slack messages and texts I’ve responded to on weekends since freelancing

Those achievements look good on paper, but they don’t actually get me excited. (Slack might be the one exception.)

Right now, I’m relieved to feel optimistic about my career again. I’m proud of myself when I’m self-promotional on LinkedIn with only a flash of embarrassment. I’m giddy — and terrified — when I turn down client work to spend more time on my own projects.

Stepping away from a full-time role has given me space to figure out what I want for the next phase of my career.

I don’t want to trade my soul for a salary. I don’t want to be a big bad CMO. I don’t want to devote 40+ hours of my week to marketing something that’s not mine.

I am not unique. I’ve spoken with so many of you who are seeking more meaningful, flexible, and creative careers.

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When I first had these feelings about work, my therapist told me, gently, that lots of people hate their jobs and still find a way to be happy. That’s not my path. My career gives me purpose, and finally, my ambition is starting to take a new shape — one that serves me first and others second.

If any of this feels familiar, this next chapter is for you.

False Start is evolving to serve marketers questioning the traditional career path.

Since I launched on Substack, my About page has read, “Your career isn’t a race. There are no penalties for false starts.” The idea of second beginnings has always been central to my writing. Now, I’m sharpening my focus to serve the growing group of marketers who want more for their careers.

For some people, that will mean blowing it all up and starting fresh in a different industry. For others, it will mean a quiet shift toward a creatively fulfilling hobby outside of working hours.

If you’re uninspired by your career, in the middle of a pivot, or looking for permission to start, I think you’ll enjoy what’s to come:

• EXPANSION VIA Stories: I’ll show you what’s possible through conversations with marketers who walked away from traditional paths — and those who stayed but built creative, alternative practices alongside their 9–5s.

• CONTEXTUALIZATION VIA Signals: I’ll help you understand why this shift is happening as more marketers reconsider (or reject) the traditional path.

• COMPANIONSHIP VIA Field Notes: I’ll bring you along on my journey toward a portfolio career, including how I think about work, my schedule, my finances, and how I find clients, so you feel less alone in your own transition.

• GUIDANCE VIA Playbooks: I’ll help you move through your career evolution with actionable advice on personal brand, career design, self-employment, and more.

I’m also adding a new layer to False Start: a paid tier with practical support for marketers in the middle of a pivot.

Many of you are rethinking your careers right now, and I want False Start to be a place that helps you through it, not just inspires you from a distance. The paid tier is where I can offer deeper guidance, more tools, and behind-the-scenes clarity.

Moving forward, free subscribers will receive 2 newsletters/month, and paid subscribers will receive weekly newsletters, including the exclusive content outlined above.

If you’ve been enjoying False Start and want to support further, becoming a paid subscriber is the best way to help, and now’s the perfect time: I’m offering 20% off annual subscriptions—just $48 instead of $60. You’ll also lock in this discounted rate forever. The offer will expire one week from today on 1/14.

Ultimately, the paid tier will allow me to spend more time writing, editing, and building False Start. I have so many ideas. An IRL offsite? A Slack community? A virtual Artist’s Way group?

I’m so grateful for your support and can’t wait to see where this year takes us.

xx Kate

I have a funny relationship with my chosen field, and it’s evolved a lot since I entered the industry in 2013.

In my early twenties, when I was new to New York and on dating apps, I’d answer the classic first date question about what I did for work with a sarcastic, “I work in marketing like every other basic bitch in Manhattan.”

Younger me was embarrassed by my field of work. I felt like marketing was trivial compared to other business roles like FINANCE or OPERATIONS or STRATEGY. At one point, I became so obsessed with making my career seem serious that I convinced my boss to add “business development” to my title when I got promoted.

It took me about eight years to realize that in business, marketing is as serious as it gets — but in many ways, the field still doesn’t command the respect it deserves. Why does an entire industry responsible for growth, storytelling, and revenue still get treated like a creative hobby?

Recently, a photo of a billboard reading “marketing is the hardest job that looks easy” popped up in my Substack algorithm. It’s 100% AI-generated, but the industry phrase persists, and I haven’t been able to stop thinking about it.

I’ve felt this tension on and off throughout my career. The public sees only the final product of marketing, not the hundreds of hours of research, briefing, stakeholder alignment, and production that go into it behind the scenes. And because marketing is so broadly consumed — you can’t avoid it if you tried — everyone from your neighbor to your ex-boyfriend thinks they can do it, too.

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Emily in Paris certainly isn’t doing us any favors, either.

The show portrays marketing as a whimsical, improvisational art form performed by a woman in couture who never misses a party. There are glimmers of truth now and then, but on the whole, Emily in Paris anchors on drama and glamour, skirting over the real work of marketing: robust insights, cross-functional collaboration, and the pressure to drive results.

Then, there’s the real-life version of Emily: the #marketinggirl posting aesthetic day-in-the-life videos. Apparently, Meta AI describes the hashtag as “empowering women.” Do reductive videos of women in cute outfits and pretty offices with photogenic coffees feel empowering to you?

These stereotypes don’t just show up on screens, either. In many offices, marketing gets labeled the “fun” department. I can’t tell you how many times I’ve been asked to help plan a company-wide party under the guise of, “You’re so creative!”

It’s hard not to internalize these narratives and accidentally make them your own. But here’s the uncomfortable truth: a lot of the stereotypes we hate about marketing are ones we also perpetuate.

The rest of this piece is for paid subscribers.

Below, I get into what this means for marketers — and how we can share our work in a way that earns trust, respect, and long-term impact.

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Lately, I’ve been thinking about motherhood, work, and identity in a way that feels less hypothetical and much more real. Two of my closest friends and my sister had babies in the last year, and it’s made me reflect on how limited my perspective used to be. In hindsight, I’m embarrassed by my attitude toward parents at work, and it’s part of the reason I wanted to bring this topic to False Start.

No matter your relationship to parenthood, everyone can benefit from a deeper understanding of the experience, especially if you’ll one day support, manage, or work closely with someone returning from leave.

So, I talked to four marketers about maternity leave, their emotions upon returning to work, and the shifting priorities that come with motherhood.

Today’s letter is long (but tender, honest, and so, so good) — I’d recommend opening it in your browser for a better reading experience.

Keep reading for reflections from:

• A senior brand manager who was anxious about leaving her daughter in someone else’s care

• A self-employed marketer who only gave herself five weeks of maternity leave

• A senior manager who felt supported returning to work on a team full of moms with young kids

• A marketer who got laid off while pregnant and started freelancing

Natalie Pace

“Five months away is really a long time, and in those first few months back, I felt really lost and insecure about myself and my value to the company. “

Role: Senior Brand Manager, Flamingo

Company Size: 500-1000 employees

Maternity Leave Length: Five months

Was there coverage for your role while you were out?

Yes, a contractor was hired to partially cover my role with support from another team member.

How much care support did you have returning to work?

I hired a full-time nanny to care for my daughter upon returning to work. I was also really lucky to have an excellent return-to-work policy and was able to work part-time the first month back to ease into working parenthood.

Describe your emotional state upon returning to work. How did you feel leading up to it?

I had a lot of anxiety about returning to work. I was somewhat of a control freak when it came to my daughter and was convinced that no one else could take care of her properly. The thought of leaving her with someone I barely knew made me extremely nervous. The week before I went back full-time, my (wonderful!) nanny and I did a transition week together. The first time I actually left my daughter alone with her, she was inconsolable (and honestly so was I?). I left the apt for less than an hour to run an errand, and I’ll never forget the sinking feeling - like, how am I going to do this for eight hours, every day, Monday-Friday? It was such a low point…this feeling that I was running on empty at the end of my maternity leave, yet the light at the end of the tunnel (returning to work) filled me with such dread.

How was the experience of returning to work? What surprised you most?

I think I had a pretty positive return-to-work experience, especially with my re-onboarding phase and the chance to ease back in part-time. What surprised me most was that it wasn’t a complete disaster! I actually felt a lot better once I started working again. Having some separation from my daughter while allowing others to care for her was good for both of us. Returning to work also helped me reconnect with myself after becoming a mother. It felt good to get out of the house, see my coworkers, and use my brain in a different way.

That said, while I’d mentally prepared myself for the anxiety and guilt of leaving my daughter, I wasn’t prepared for how disconnected I’d feel at work. Five months away is really a long time, and in those first few months back, I felt really lost and insecure about myself and my value to the company. I found that I was trying to prove myself by pushing myself harder. There was a stretch when I’d come home, do bath and bedtime with my daughter, then log back on until 10 p.m. to prepare myself for meetings and get up to speed. Looking back, I probably didn’t need to do that, but at the time, I felt like I had to work harder to prove my worth after being away for so long.

Has your relationship with work changed? If so, how?

I really do like to work, and I truly love what I do, but nothing will ever matter more to me than my family. Since becoming a mom, I’ve learned to take professional setbacks way less personally. Things just don’t irk me as much as they once did — perspective is a real game-changer. I’m grateful for the healthier relationship I have with work now that it’s not my end-all, be-all. What’s been harder is dealing with the constant juggle and PLANNING that comes with working motherhood. Realizing that it’s never going to be perfect has been a tough pill to swallow, but it’s also helped me let go of some of my own unrealistic expectations of perfection - and in that way, it’s been surprisingly freeing.

Tyeal Howell

“Looking back, I realize I put so much pressure on myself to ‘return to work’ as a self-employed marketer and first-time mom, because career achievements felt more measurable than motherhood.”

Role: I was self-employed for my first, and working full-time as a Media Solutions Manager at an advertising agency for my second.

Company Size: I hired one other employee while self-employed. For my FT job during my second maternity leave, the company had ~200 employees.

Maternity Leave Length: My self-employed maternity leave was about 5 weeks long — I was impatient to get back to work. My salaried maternity leave was technically 10 weeks; however, my manager at the time told me to take an additional 2 weeks, for a total of 12 weeks.

Was there coverage for your role while you were out?

When I hired my first employee as a first-time mom, I delegated tasks like community engagement and newsletters to stay active online without the pressure of creating content myself. As a salaried employee, the company hired a backfill for my role, and I trained her for about a week and a half before going on leave. Unfortunately, she wasn’t a great fit for the role, and her contract was terminated before my return.

How much care support did you have returning to work?

Looking back, I realize I put so much pressure on myself to “return to work” as a self-employed marketer and first-time mom, because career achievements felt more measurable than motherhood. Unlike marketing, there are no formulas or measurable funnels for early motherhood. What works for one baby might completely flop for yours, and a good night’s sleep one day can turn into a gassy afternoon the next day. It’s a game of trial and error, learning to trust yourself, and giving yourself grace. When I returned to a salaried role and came back from maternity leave, the difference was night and day: my position was backfilled, colleagues were available for 1:1s immediately upon my return, and I could jump right back in, feeling like I’d never left.

Describe your emotional state upon returning to work. How did you feel leading up to it?

I was an anxious self-employed marketer, which is why I chose to return to a salaried environment. I definitely returned to work anxiously, too. My return as a salaried employee was calm and confident. I felt solid in my day-to-day workflow, and being able to stay home with my baby during the day was an absolute blessing.

How was the experience of returning to work? What surprised you most?

Returning to work after maternity leave felt surreal. I remember during my self-employed days, I was essentially running everything myself, answering emails at all hours, constantly creating content just to stay visible, and I braced myself for returning to that chaos. Stepping back into a salaried role was like walking into a well-oiled machine. My position was backfilled, colleagues were ready to catch me up, and clear processes were in place. I was surprised by how natural it felt to just show up and do my job. It made me realize how exhausting my previous way of working had been and how much freedom structure gave me, especially while balancing motherhood.

Has your relationship with work changed? If so, how?

Motherhood shifted everything for me. The thrill of the self-employed hustle, the constant content creation, and the hunt for the next client used to energize me in my early 20s. After becoming a mom, it felt draining. I wanted more than just professional wins; I wanted stability, security, and a rhythm that allowed me to be present with my daughter. Being a salaried employee gave me that balance. It changed how I measure success. I’m no longer chasing numbers, but building a life where my work sustains me, not depletes me, and where I can show up fully for both my career and my child. It’s still a challenge, don’t get me wrong, but my definition of a successful life has completely changed.

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Leah Hamilton

“I took my first work trip after a few weeks back, and my husband and baby were both welcome at our team dinner and in the office to nurse during lunch breaks. “

Role: Sr. Manager, Global Brand Marketing, Teva

Company Size: ~200-300 employees

Maternity Leave Length: Five and a half months

Was there coverage for your role while you were out?

Yes, two separate contractors were brought on to cover different areas of my role & responsibilities, and I spent time onboarding them prior to my leave.

How much care support did you have returning to work?

We had originally planned to send my son to daycare, but our efforts to get him accustomed to bottles ultimately failed, so we decided we’d be most comfortable with him having 1:1 care in our own home, where I could assist with feedings as needed. My husband and I staggered our leaves, so when I went back to work, he was the primary caretaker, and our nanny started shortly thereafter. I work from home, and am still nursing, so I was able to be pretty involved while starting back up at work, and still am.

Describe your emotional state upon returning to work. How did you feel leading up to it?

I spent the entirety of my maternity leave SO anxious about returning to work and determined to figure out how to spend as much time as possible with my son. Before having a baby, my work was my baby - my purpose, identity, and how I proved my worth to myself. I couldn’t imagine having another priority that was more important.

How was the experience of returning to work? What surprised you most?

Shockingly (to me), going back to work was nowhere near as bad as I thought it would be. I work on a team full of moms with young kids, and I was welcomed back with open arms. I found that it wasn’t actually too difficult to stick to my new boundaries (i.e., signing off at 5 p.m.), and I felt empowered to use my brain in a strategic way again. I took my first work trip after a few weeks back, and my husband and baby were both welcome at our team dinner and in the office to nurse during lunch breaks. I feel very lucky to be a part of such an understanding and flexible work environment.

Has your relationship with work changed? If so, how?

At my core, I think I’ll always be a people pleaser and strive to be a high performer. In that sense, my relationship with work hasn’t really changed - I still put my all into my job while I’m working, and sometimes do find myself working after my son goes to sleep (although much less often than before). However, the constant feeling that work is my identity has faded as I watch my son grow and discover the world. I’ve found a new lifelong purpose in being his mom - a role that can never be taken from me.

Emily Drewry

“Even though I knew I needed to say yes to (freelance) opportunities to help pay for our lives, it felt like I was ‘choosing’ not to be with my daughter. “

Role: Unfortunately, I was laid off while pregnant, so I didn’t have paid maternity leave. Instead, I freelanced leading up to my delivery.

Company Size: NA

Maternity Leave Length: Not having a full-time role to return to was a double-edged sword. On the one hand, I got to be with my baby for almost 9 months, a time I wouldn’t have had otherwise and will always cherish. On the other hand, that long period of time took a big financial toll on my family. It was also tough for me, as a high-performing, career-minded individual, not to know what my next step was.

Was there coverage for your role while you were out?

I didn’t have a full-time role on hold, but I did think a lot about when and how to start freelancing again after a few months of being completely offline (work-wise). I said yes to a project this spring that was very aligned with my expertise and because I believed in the work, but otherwise, I stayed out of the freelance game. Taking care of the baby full-time was literally a full-time job. There was no “work while the baby naps” for me… either because she didn’t nap, or only would nap in my arms, or I had to do 10 million other household things while she did sleep.

How much care support did you have returning to work?

I started ramping up my freelance work after five months of focusing purely on childcare. I’m grateful to have a network that brought me opportunities, so I was able to focus on doing the work rather than looking for it. That said, I did spend a lot of time looking for the ideal next full-time job. I also had the support of my in-laws, who would chip in to watch the baby whenever I needed to join a meeting or crank out some work. In the evenings after she went to sleep, I’d fit in a few more hours on my laptop.

Describe your emotional state upon returning to work. How did you feel leading up to it?

Starting to freelance again was really hard. Even though I knew I needed to say yes to opportunities to help pay for our lives, it felt like I was “choosing” not to be with my daughter. It felt murky — watching her most of the time and trying to fit in some work and job applications in the little pockets of time I had. When I did return to work full-time, it felt like a huge relief — I had missed being around adults and having intellectual conversations. Taking her to daycare, however, was absolutely brutal. I trusted the place we picked, knew I wanted to work, and STILL couldn’t stop crying for days. I’m not the least bit surprised that so many women are pursuing self-employment during this era of their lives. It’s HARD to make it all work.

How was the experience of returning to work? What surprised you most?

My situation was unique in that I was looking for a new full-time role and had the financial stability to be picky. I wanted to choose a company that understood the challenges of being a new parent, offered sufficient benefits and good compensation, and provided a flexible environment, but also offered adequate intellectual challenge.

I’m incredibly lucky to have found a job right when we were planning to start daycare for our daughter. I was able to primarily work from home, which was so helpful since I was weaning off breastfeeding at the same time. I was surprised by how emotional I was at first — and guiltily grateful to not be the main caretaker all day long. It requires so much patience, focus, and energy — so different from working a desk job. So far, I’ve been really happy to be back at work, except for a tough day here and there when I really miss her and feel badly she’s achieving milestones with someone else.

Has your relationship with work changed? If so, how?

1,000%. I knew I would want to go back to work — zero part of me planned to stay home, at least at this point in my life. But I absolutely have set harder boundaries than I did before having a child. When I need to pick her up from daycare, I am offline. No hesitation. It can be difficult to balance everything emotionally, but I do find myself even more productive during the day, so I can be completely present with her in the evenings. I’m still extremely committed to my work and have a lot of aspirations, but it’s fallen down the list of big life priorities. That said, my feelings change from day to day. I hope we continue to evolve how we think about working, parenting, and the confluence of both — this is such an important conversation.

I’m so grateful to Natalie, Tyeal, Leah, and Emily for their vulnerability during these interviews. As Emily said, these conversations are so important — but painting a picture that’s anything less than 100% honest does no one good.

What stood out to me most is how much tenderness sits underneath the logistics of returning to work. Calendars, childcare, onboarding, pumping, Slack messages — all layered on top of a major identity shift no one can fully prepare for.

I hope this letter gives you a deeper understanding of what your colleagues, friends, past or future self may go through.

If you enjoyed this newsletter, please like this post and leave a comment. It helps more readers discover False Start — and your feedback helps shape what I write next.

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Maybe it was because I was fresh off a red-eye flight, only running on a few hours of sleep. Maybe it was because it was my first day back at work after time off.

Maybe it was because I needed an entirely new career.

Last week, my therapist told me she admired how I listen to and act on my intuition. I laughed. “Thank you,” I replied, “but I wish it weren’t such a painful process.”

Every time I’ve made a career change, I’ve experienced a gap between the original feeling that sparks desire for change and the motivation to do something about it. I’ve been aware of this waiting period for a few years, but that doesn’t make it any easier to endure.

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I first acknowledged my unhappiness with work in August 2024. I finally made the big, scary change and left my job in April 2025, a full six months later. Since then, I’ve spent a lot of time reflecting on that stretch of time. The waiting period felt like monotonous agony (I wasn’t making any progress!), but in hindsight, I can see that I moved through nine distinct emotional stages.

I want to share what those stages looked like for me in the waiting period between inspiration and action. I know how frustrating it feels to want change but not be able to make it happen. If you’re in it right now, I hope this helps you notice the subtle emotional shifts that are quietly moving you toward where you want to go.

The next part of this story is a little more personal, so I’m sharing it with the community of paid readers who make this space possible.

If you’d like to join us — especially if you’re in your own waiting period — you can upgrade to read the full newsletter: all nine emotional stages that led me toward change.

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In April, I left my full-time role to pursue self-employment because I thought it would make me happy. Ambition has let me down before, but I still cling to it in desperate moments. My brain likes the familiar, and I’ve devoured narratives about the promise of success for my entire life.

Despite the career change, I still feel restless. The burnout burns on.

I often escape to the movie theater in my brain, screening a trailer for my perfect future: I’m living in a wood-paneled Brooklyn brownstone and working on creatively challenging marketing projects while pursuing my Pilates certification, taking a graphic design class, and volunteering at an animal shelter. (If that doesn’t sound realistic, take a look at your daydreams and get back to me.)

When I’m not replaying my 2026 vision, I dig up the archives of 2023. I was fresh off a breakup — the kind that grabbed me by the shoulders, shook me, and shoved me back into the spotlight of my life. I watched a looping montage of myself on slow walks, scribbling away at morning pages in bed, laughing over dinners with friends. Everything felt enchanting.

Outside of the theater, in my real life, I grew frustrated with myself. Why wasn’t I content? Did I need to go back to therapy? See a psychiatrist? Get a business coach? Take three months off? What was going on?

One of the few benefits of overthinking is that occasionally, the brain produces a helpful thought. Something in me shifted once I realized the happy memories I was nostalgic for only existed because I was extremely present with them.

Historically, I’ve stumbled upon presence through external forces. Big life changes (a breakup, a move, a job change) and novel experiences (traveling to a new place, attending a concert, falling in love) have helped pull me out of my head. But they haven’t been able to keep me there.

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I knew my return to presence needed to be an inside job. I didn’t want meditation to be the answer.

I tend to wield meditation like a Swiss Army knife — slicing and sawing off feelings I’d rather not experience. My thoughts are racing before bed? Meditate. Stressed about work? Meditate. In a bad mood? Meditate.

(If you know anything about meditation, you know this is not how it’s meant to be used.)

Two months ago, I begrudgingly began a meditation practice — the kind you do daily, whether or not you want to. The beginning was slow, and I was annoyed by the extra task on my to-do list. To make matters worse, I didn’t notice immediate changes to my disposition, and I certainly didn’t enjoy closing the curtains on my movie theater brain. Imagine having to choose between watching your daydreams or a blank screen. Which would you pick?

But sure enough, the glimmer of presence started to creep back into my life. One day, on a walk along the West Side Highway, I was struck by the glint of the water and the way the light filtered through the trees. A few weeks later, I spent three days in Nantucket with my boyfriend. I felt peaceful for 72 hours straight. Maybe that’s a normal vacation response for some people, but it’s certainly not for a control freak like me.

Those moments motivated me to keep going. Two weekends ago, I went deeper and attended a meditation retreat with my mom. Most of our time was spent learning about meditation, discussing the challenges, and practicing various techniques. We sat for three hours at a time, observing our internal experiences amid occasional sniffles and frequent body aches. The rest of it was spent talking with 12 strangers about death and uncertainty and fear.

As I get older, I’m increasingly fixated on the passage of time. I want to slow everything down, even as nostalgia and daydreams pull me in the opposite direction. Ambition can lead to an unhealthy preoccupation with the future. Discontent can lead to an unhealthy preoccupation with the past. Lately, I’ve been guilty of both.

While I’m still new to this practice, meditation is starting to expose the delusion of my ambition. If I feel best when I’m present, what does that mean for the promise of achievement? Don’t get me wrong, I still want — a lot, actually — but the wanting feels less urgent. Achievement isn’t the key to my happiness. I don’t know if presence is, but it feels more promising so far.

After all, whatever you achieve, there you are.

If you have experience with meditation, I’d love to hear about how it’s changed your mindset, your relationship with work, your ambition — all of it. See you in the comments.

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After a few months, I started to resent my weekly reminders. Updates became infrequent and haphazard. Finally, they disappeared entirely. I ended up accomplishing a few of my objectives and failing others. More importantly, I hated the process.

Life is for experiencing, growing, and enjoying — not generating shareholder value. Why was I treating myself like a business?

I’ve come to realize that my desire to set goals often stems from ego. I use achievement as an all-purpose balm: to soothe anxiety and protect against insecurity. Traditional goal-setting practices have never helped me feel more motivated. If I want something badly enough, I’ll do it anyway, without a task in Asana. The other problem? I usually don’t know what my future self wants. And if you’re like most people (thanks, projection bias), you probably don’t either.

After abandoning my OKRs, I shifted focus towards accepting daily life over chasing long-term goals. One day, while mulling this over with my therapist, she offered an idea: would I like to try an exercise to identify my core values? Never one to turn down a self-improvement tool, I responded with an emphatic yes.

As I understand it, this practice can be helpful if you:

• Want to feel more connected to your work and daily life

• Don’t identify as a goals person, but like the idea of using a framework for personal growth

• Have a significant change or decision on the horizon

It’s been three years since we identified my values, and I still check in with them every night. For me, they serve as a compass and a tool for connection. I’ve used them to answer big questions, like “Should I go freelance?” and to find meaning in my day-to-day work.

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I’ll walk you through how to identify your core values, but first, I should clarify: I’m no therapist. I’m just a human searching for meaning, and this is something that’s worked for me, both in my career and personal life.

How to identify your core values

Step 1: Print out this list of values.

Step 2: Circle all of the values that feel important to you.

Be discerning and refrain from judging yourself. At first glance, you might think every single value is important to you. Possibly, but some will be more meaningful than others. When I did this exercise, “kindness” didn’t jump out at me, but “honesty” did. Does that make me a monster? Your call.

Step 3: Write down all of the values you circled on a separate piece of paper and cut the list in half.

Do a few of your values mean something similar? Did your ego select any? If so, they may feel less resonant upon second glance. Cross them out.

Step 4: Do a quick journaling exercise.

Ask yourself, “What does this value mean to me, and how does it show up in my life?”

Step 5: Narrow down your list to 3-5 values.

The journaling exercise should help. You’ll learn which values speak to you the most, in that you either feel very strongly about them, or that they show up frequently in your choices and behavior.

Feel free to play around with a thesaurus, too — language matters. Sticking with my example from above, I originally selected “honesty,” but ended up using “integrity” instead because it felt more representative of my values.

How to use your core values

Nearly every night for the past three years, I've checked in with my values using an app called Daylio. If you upgrade to the paid version ($4.99 per month), you can customize the sections and items within them, as I’ve done below. After I get in bed, I review my day and select the values that were activated. Did I struggle with a problem at work? That’s challenge. Did I do something new, even if it’s visiting a coffee shop I’ve never been to? That’s novelty. Did I learn something about myself? That’s personal growth.

The whole exercise takes five minutes, so I rarely have an excuse to skip it. Regular check-ins help me feel more grounded in my day-to-day, and over time, they’ve also supported bigger decisions. Because Daylio stores all my data, I can zoom out and see which values appear frequently and which I’ve been neglecting. I’ve used that information to make decisions and have applied my values as a framework to evaluate new opportunities.

I started 2021 with goals, but now I have something even better: clarity about what matters to me, and a practice that helps me stay close to it. My core values have guided me through job changes, a transition to self-employment, and numerous other challenging work moments. They’ve also supported me through break-ups and other difficult transitions. This is so much more than a career tool.

Despite our cultural obsession with 5-year plans, New Year's resolutions, and big, hairy goals, you don’t need to have it all figured out. You just need to know what matters to you, and how to stay close to it.

Has a personal value ever helped you make a tough career decision? I’d love to hear how it showed up.

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Me too.

You used words like “existential,” “burnout,” “uninspired,” and “broken.” The phrase I’ve been tossing around is “quarter-career crisis.” Word choices aside, I know we’re talking about the same thing.

I’ve squarely avoided this topic on False Start because it feels too vulnerable to share while I’m living it.

It’s easier to write about an experience after it’s over. Everything feels clearer in hindsight. Zoom out, connect the dots, and tie them together with a bow. The problem? Time erases the complexity of emotions. The memory of the feeling is not the same as the feeling itself.

I entered the workforce during the “lean in” era, devouring Sheryl Sandberg’s bestseller a month before I graduated from college. Instagram exploded after that, and with it came the birth of the “girlboss.” Sophia Amoruso was the poster child, but there were others, too. Payal Kadakia founded ClassPass in 2013. Emily Weiss launched Glossier in 2014. Ty Haney, Audrey Gelman, and many others followed suit.

The social posts, books, and interviews surrounding these women led me to believe that a successful career would bring me happiness, just as I thought it had for them. That’s a big assumption, but I was only privy to their highlight reels. Can you blame me?

To be clear, I don’t fault my role models for my misunderstanding. They don’t owe anyone complete honesty about the lows of their careers; the challenges that arose as their titles, salaries, and responsibilities grew. Besides, leaders often can’t share their most challenging moments due to legal and fiduciary reasons. There’s also the question of time and desire. Do they want to share? Do they have the space to? Even if they could speak about these topics, would it represent the whole of their experiences? Time and psychology tend to diffuse the truth.

There are two phenomena we can thank for that. The peak-end rule, coined by psychologists Daniel Kahneman and Barbara Fredrickson, states that memory is most influenced by feelings at the peak (the most intense moment) and the end of the experience. As such, recall is skewed, and we tend to forget the nuanced and shifting emotions that occur across time. Then, there’s the fading affect bias, which describes how the emotional intensity associated with negative memories fades faster than that of positive memories.

Combined, these make it difficult to share past experiences in full color. The career triumphs I consumed from my role models were incomplete stories. Unfortunately, my younger self used them to construct beliefs about professional success, mainly regarding how achievement would make me feel. It’s taken time and experience to learn that my expectations were more rooted in fable than fact.

Here’s what happened: I landed my first full-time job at 22 and enthusiastically climbed the ladder for over a decade. Finally, I achieved the fancy title and the salary. I was thrilled. Then came the existential dread. Panicked, I thought to myself, “This is it for the next thirty years?” Many contributing factors led me here — the chaos of early-stage startups, the pace of the marketing industry, and my own ambition — but my overidealized career expectations played a starring role.

The career crisis is, of course, a common and somewhat predictable experience: a person works their way up only to realize they’re unhappy. Sure, I could blame this on late-stage capitalism and call it a day. But that won’t help me design a career within the system that I can make peace with and derive fulfillment from.

I trust that eventually, I’ll look back on this phase of my life with gratitude. Though my professional frustration has already pushed me in a better direction, I’m still in the thick of it. The narrative I’ll one day tell will be different from the one I’m living right now. As the peak-end rule and fading affect bias influence my future reflections, they’ll never capture how I’m presently experiencing the reality of this life stage.

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Still, I struggle to explain my career disillusionment — even to myself. Since I can’t explain it, I’ll tell you how it feels. I feel disconnected, as if I’ve snapped off a piece of my identity like a Lego. I feel weathered and jaded. I’m only 34; I shouldn’t be this tired. Without a goal to work towards, there’s nothing to anchor my ambition. It’s free-floating, swirling, haunting me. I’m both nostalgic for and resentful towards my younger self, who was single-mindedly focused on achievement.

In my twenties, I used external stories to shape my priorities. Now, I’m turning inward. My emotions, gut feelings, secret desires, and personal interests will guide me. The most important thing I can do is tell myself the truth and listen.

I’ll never discourage you from chasing traditional career achievements. The pursuit of a raise, promotion, title, and salary can be worthwhile. They can also be shiny objects that distract you from your true nature. Instead, I encourage you to get quiet. Pay attention. How do you feel?

Do you dread the work week? Is there a whisper that says, I don’t think this is for me? This effort feels meaningless. I’m not myself in this office. 10 years ago, mine said in a shy murmur, I want to work for myself. I want autonomy and independence. I ignored her for a while, but she’s only grown louder with time.

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One of my ugly truths is that up until a few years ago, I regularly experienced bouts of insecurity at work. When I reflect on those times, I realize I held a number of beliefs that were fundamentally incorrect.

Insecurity prompted me to search for reasons why I lacked confidence, and my brain whipped up a bunch of well-meaning yet ill-advised ideas. Hindsight is always 20/20, and the root of insecurity is now excruciatingly apparent: I lacked confidence because I was doing something new for the first time. I hadn't yet proved to myself that I'm actually pretty damn resourceful and smart.

So, I offer up the worst beliefs I held in my early career. My hope is — if you identify with any — you’ll consider abandoning them entirely. I simply want to help other early career women (and men) learn from my own false start.

Idea #1: "I need marketing ‘hard skills’ to be successful."

When I left the media world to join my first brand, I got in my head because I didn't know the “right” way to craft a marketing strategy, optimize ad creative, improve email performance, make influencer marketing more effective…the list goes on and on. I thought I was fundamentally missing out on very specific skill sets that someone would hopefully impart to me at some point.

The bad news: no marketing fairy godmother came for me.

Still, I was able to figure most things out by carefully observing the people around me (laterally, upwards, downwards), learning how to bring structure and rigor to my thinking, asking for feedback, and trying, failing, and trying again. In marketing, there's no one way to do something, anyway. There are only best practices.

Idea #2: "Changing jobs so frequently means I'm bad."

To be fair, this belief never stopped me from changing jobs (I hopped around a lot) but I carried a bit of shame for quite a while, feeling like something was wrong with me because I decided not to stay in the same place for a long time. Some of this came from well-intentioned advice from my parents, but the reality is, a successful career is built differently today than it was thirty years ago.

For what it’s worth, I've rarely been questioned about my job-hopping while interviewing, and it's never stopped me from landing an offer. Rather, it’s given me a wide range of experiences across industries, accelerated my compensation growth, and ultimately made me a more nimble and adaptable marketer.

Idea #3: "When the company does poorly, this means I'm bad at my job."

Have you ever heard of a little thing called "product-market fit"? I hadn't until a few years ago.

My first-ever brand-direct role was extremely challenging for several reasons. Our marketing efforts saw mediocre returns, and no matter what I tried or who I talked to, nothing improved meaningfully. I took this extremely personally. I felt like business performance was 100% my fault, and it also made me anxious and shaky when I started interviewing for a new role: I didn't have strong revenue numbers or engagement rates to show for all of my hard work.

Usually, I'm all for taking responsibility, but in this case, I took it too far. Customers didn't want what we were selling, at the price we were selling it, from the channel we were selling it through. It wasn't a reflection on me, and I went on to be much more effective in my next role.

Idea #4: "I will get the promotion and the raise if I outwork everyone around me."

In a perfect, fair world, effort and results are always rewarded. Sadly, we don't live in a perfect, fair world. I say this not to deter you from working hard and striving for more but to temper your expectations. Don't go above and beyond just because you want the promotion, raise, or bonus. Go above and beyond because you want those things AND, enjoy the effort, want to learn, and care about what you're doing. And if this isn’t the case…maybe refer back to Idea #2.

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Idea #5: "Public speaking terrifies me and always will."

My first job out of college was on the sales team at the New York Post. The Post was an incredible place to start my career for many reasons, but I detested the work. The two tasks I hated most involved public speaking: calling local businesses to pitch remnant advertising and helping pitch campaigns to agencies over the phone and through in-person meetings. But the worst part was that I convinced myself I couldn't overcome it.

As it turns out, that wasn't true. I've had so much practice since then, which has helped more than I could have hoped. Public speaking still makes me nervous, but I liken it to the feeling of butterflies — it gives me a rush of endorphins, and I always feel proud of myself afterward.

Idea #6: "I need a 10-year plan to achieve success."

What is it they say? "You make plans, and God laughs"? They're not wrong.

I used to think I needed a clear goal and plan to achieve success, lifelong happiness, and self-actualization. Then, I learned about projection bias. Projection bias is a self-forecasting error where you conflate your current beliefs and values with the beliefs and values of your future self. Have you ever committed to a plan and on the day of, decided you didn’t want to go? Or achieved something only to realize it's not what you want? You've been subject to projection bias.

Most of us don't know what we want in the future, even if our current self thinks we do. Instead of writing a 10-year plan, try meditating on the mysteriousness of life. I think it's more useful.

Have I solved all of your insecurities? Kidding. I’d love to hear what resonated with you (and what didn’t). See you in the comments!

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If you want perspective on a different insecurity you’re experiencing or advice on anything else, drop a question here.