Me, You and Everything I Know About Career Pivots in 5 Bullet Points

Opportunities come from being seen

Feb 21, 2025

Career pivots, reinvention, transformations feel messy when you’re in them. When I’ve been mid-pivot—shifting from editorial to tech, running a startup, or figuring out what’s next—it’s felt chaotic, uncertain, and sometimes like a tragic idea. But every time, I’ve landed somewhere new with a clearer perspective. And when I look back on my experiences, the throughline is obvious.

I’ve learned a few things along the way—some the hard way, some through luck, and some by just paying attention.

Here are five things I know for sure about making big career moves:

1. Put yourself in the mix—opportunities come from being seen.

Every major career move I’ve made started with connecting to people online. I’ve always shared what I was working on—whether it was a blog, a zine, a weaving, or an idea—and that openness led to opportunities. My job at Metropolis happened because I had a design blog and connected with the creative directors who were redesigning the magazine. If you want to attract opportunities instead of chasing them, get comfortable sharing your work in public.

2. If they can do it, so can you. Permission granted.

I believed Lex needed to exist as an app before I knew how to build an app. No one told me I could do it—I just decided I would. A friend recently said the phrase arrogance of imagination (from Hanya Yanagihara’s “A Little Life”), and it resonated. The ability to act on an idea is a skill. You can teach yourself just about anything now. You can figure it out as you go. People are mostly making it up anyway.

3. Timing is everything—but you have to pay attention.

Luck and timing play a huge role in success, but they aren’t random. I started Herstory when Instagram was on the rise, which helped it grow. But if I were starting today, I wouldn’t use IG—it’s not the platform it was 10 years ago. Paying attention to trends, culture, and emerging platforms lets you place yourself where momentum is already happening. It’s about stepping onto the right wave at the right time.

4. Don’t hold on too long—make the move before the breakdown.

I tend to stay in things too long—jobs, roles, situations that no longer fit. Looking back, I wish I had trusted myself sooner instead of worrying about how things looked from the outside. With Lex, I could have said from day one, I don’t want to be CEO, and found another solution instead of waiting until I had no choice. The moment you start wondering if you should move on, you probably already have your answer.

5. It all makes sense later.

When you’re in the middle of a pivot, it can feel chaotic—like you’re making a drastic, disconnected move. But when you zoom out, the path always makes sense. Your skills, experiences, and patterns follow you, even if you don’t see it in the moment. Every move I’ve made—AOL chat rooms, blogging, design, startups—has been connected in ways I couldn’t have predicted at the time. Trust the throughline.

TL;DR cheat sheet

1️⃣ Opportunities come from being seen. Share your work, connect, let the right people find you.

2️⃣ No one will tell you you’re ready—just start.

3️⃣ Pay attention to where momentum is building and step into it.

4️⃣ Move before burnout – If you’re questioning it, it’s probably time to go.

5️⃣ It all makes sense later – Every move connects in ways you can’t see yet.

If you’ve made a big career or life change, what’s something you learned?

I’d love to hear—let me know in the comments!