There’s something wild and raw about the moment you realize the career path you’ve been on—maybe for years—isn’t quite it. Maybe it doesn’t light you up anymore. Maybe it never did.

For me, this moment didn’t show up as a lightning bolt of clarity. It arrived quietly—during a long walk, between Slack pings, in a late-night journal session where I scribbled the question I was too afraid to fully answer: What if I’m meant for something else?

If you’re here, reading this, you’ve probably felt that nudge too. You’re not alone. And you’re not crazy for wanting something different.

This guide is for you—the dreamers, the burnt-out, the multi-passionate, the people who used to love their jobs but no longer feel aligned. Let’s talk about how to actually transition careers—not just in theory, but in a way that feels grounded, brave, and doable.

Step 1: Know That Switching Careers Isn’t Linear

I used to think career change was like hopping from one clearly marked train to another. In reality? It’s more like wandering through a foggy forest with a compass that changes direction every week. But the path becomes clearer with each step you take.

If you’re pivoting careers, your action plan will likely look very different than if you were staying in your industry. It’s not just about job titles—it’s about learning, unlearning, and experimenting. It’s about collecting clues that point you toward something more aligned.

Step 2: Play Detective—Investigate Roles & Paths

Don’t make assumptions. Make discoveries.

Informational Interviews saved me more times than I can count. I talked to folks who made similar transitions—engineers who became PMs, designers who moved into coaching. These chats didn’t just offer insights; they helped me build relationships that later opened doors.

If you're exploring a new industry like digital health, you might ask:

• What does your day-to-day look like?

• What skills surprised you as most important?

• How did you make the leap?

✨ Exercise:

Examine the paths others with your profile have taken. What options are available inside your current company? Could you switch roles without switching industries?

Step 3: Embrace the Middle Step

Not every move needs to be The Big Leap. Sometimes a smart, strategic middle step is the wisest move. I once took a role that wasn’t my end game but gave me insider access to the team I actually wanted to join. Within months, I made that pivot.

Think of middle steps as launchpads. Could you go from consulting → operations → product? From marketing → design → UX strategy?

Start where you are. Build from there.

Step 4: Commit to a Discovery Period

We don't need to get married to our new career on day one. Date it.

Set a hypothesis and a timeline. For example:

• “By January 2026, I will explore product design through a course, a side project, and 5 conversations. I’ll then decide if I want to go all in—or pivot again.”

✨ Exercise:

What tangible discovery period can you set up? What are the 3 things you’ll try before committing? What’s your check-in point date?

This approach is backed by psychology: The technique of “mental contrasting,” coined by psychologist Gabriele Oettingen, blends visualization and realism to create motivation and clarity. Visualize the ideal. Identify the obstacle. Then act.

Step 5: Play to Your Strengths & Improve the Rest

Whenever I was switching roles, I’d sketch five circles and ask:

• What am I naturally good at?

• What drains me?

• What am I curious to learn?

Your goal isn’t perfection. It’s progress.

✨ Exercise:

Improve your weaknesses: Which skills can you build through books, podcasts, courses, coaching? Emphasize your strengths: Write down 5 stories where you thrived using your top skills.

Step 6: Uncover & Translate Your Transferable Skills

Most people underestimate how many skills are actually transferable. You don’t need to change your job title—just your language.

For example:

• “Managed cross-functional teams under pressure” → Relevant to PM work

• “Built client relationships and drove adoption” → Useful in product marketing or customer success

✨ Exercise:

Rewrite 3 results from your past roles to fit the lens of the career you want.

Step 7: Test, Volunteer, Try On the Role

Before my first formal PM job, I helped a friend redesign their onboarding flow—just for fun. That tiny project became the first line of my product portfolio.

Not ready to go full-time? Here’s what you can do:

• Volunteer with nonprofits

• Do a freelance or part-time project (even unpaid)

• Partner with friends, building something scrappy

• Help an early-stage startup in exchange for experience

✨ Exercise:

What can you commit to this month? Who can you help? What mini-project can you pitch?

Step 8: Don’t Wait—Try Multiple Paths at Once

You don’t need permission. You don’t need a perfect plan. You just need momentum.

One of the most powerful mindset shifts I’ve made is this:

“I can pursue AND, not just OR.”

I worked in product AND launched a side coaching practice. I explored writing AND helped build someone’s course. Testing different things helped me learn faster and drop the “shoulds.”

🧠 Bonus: Reflect with Self-Compassion and Strategy

✨ Understand Your Gaps:

What skills do you need to gain? Where can you get support—mentors, friends, accountability groups?

✨ Watch for Decision-Making Traps:

The Sunk-Cost Fallacy: Don’t stay just because you’ve invested time. The Planning Fallacy: Things will take longer. Plan for it. The Regret Minimization Test (from Jeff Bezos): Ask, “Will I regret not trying this?”

Final Thoughts

Switching careers isn’t just about new roles—it’s about shedding old stories.

It’s about looking at your life with fierce honesty and deep compassion and choosing to design something more aligned. Something that lights you up and sustains you. It’s a journey that requires courage, experimentation, and a little bit of spiritual surrender.

Take the next step:

Choose one experiment. Start small. Act now. Keep learning. Keep adjusting. Keep trusting yourself.

You don’t have to get it all right today.

You just have to get started.