There's No Set Path for In-House Careers . . . Here's How to Use That to Your Advantage

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Hi there! It’s Heather Stevenson.

Happy Wednesday and thanks for being here! Here’s what’s covered in today’s issue:

  • I’ve been reading Morning Brew for a decade. Today, they’re sponsoring this newsletter. If you’re not already a subscriber, take a look.

  • How to use the flexibility in in-house career paths to build a career that works for you;

  • Links you’ll love;

  • And More.

Let’s dive in.

Deep Dive

Your career path & progression is 100% your responsibility.

That sentence might sound obvious, but fully buying into it changed everything for me.

When I started law school, there was a roadmap. Take Contracts, Civ Pro, Con Law, etc. Join a journal. Get good grades. Land a summer associate role. Check the boxes, and the next step would present itself.

Even in big law, the system was still there: hit your billables, stay responsive, and become one year more senior each year—automatically.

But when I realized big law wasn’t my forever career, there was no clear next step. At that point, I had to decide what success would look like for me and figure out how to get there.

My path was especially non-linear because, for a time, I left the law altogether. But whether you’re a founder, a lawyer, or somewhere in between, not being told what to do next after years of schooling and linear career progression can feel… unmooring.

Eventually, though, I realized something liberating: I didn’t need to follow any of the paths that lawyers had followed before. I could design my own. And I could make it look like exactly what I wanted.

You can do that too.

Jumping in and out of the law? Starting something new? Switching industries or practice areas multiple times? It’s all fair game. You get to create your future.

And if you’re reading this, I’m guessing you’re in that same messy middle.

You’re experienced enough that no one’s going to hand you a five-year plan. And smart enough to know that coasting isn’t going to get you where you want to go.

So how do you chart a course when no one’s giving you a map?

Start with these moves. They’ve made a big difference for me—and they can for you too.

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1. Set clear, specific goals.

I know this sounds basic. But many mid-career lawyers I talk to haven’t actually done it.

They’ll say things like:

  • “I want to grow in my role.”

  • “I think I’m ready for the next step.”

  • “Eventually I’d like to be GC.”

But those are too general to be meaningful.  Your goal should be specific enough that you’d recognize it instantly—and someone else could help you get there.

Try this instead:

  • “I want to lead a legal team within the next 18 months.”

  • “I want to move to a company that’s earlier stage and faster paced.”

  • “I want to work in a role where I interact more with the business, and less with other lawyers.”

  • “I want to develop expertise in X, so that I can pivot to a role that looks more like Y.”

Once you know the goal, you can work backward from it. And better than just one goal is identifying various aspects of what you want your career to look like.

Then write it down. People who write down their goals are significantly more likely to achieve them. Bonus points if you actually tell someone, too (more on that below).

If you’re wondering whether this type of goal setting really works, well, I think so. 

Here’s a wild story:

In September 2020—deep in Covid lockdown—I did one of those “future me” journaling exercises. The prompt was simple: imagine it’s five years from now, and write a journal entry about your life.

So I pretended it was September 2025, and wrote this:

 “I am GC of an exciting company that is growing fast and innovating.  My team is made up of dedicated doers and leaders who know how to get things done well and efficiently.  We find a way or make one.  We are a diverse and interesting group.  I am proud that my team is made of people who are better at, or smarter than I, at what they do.  We have fun.  People wonder how we do it.” 

At the time, I wasn’t looking at roles outside of the Boston Globe, where I was Assistant General Counsel. I didn’t even want to leave the Globe yet, because I was still growing and I enjoyed both the people I worked with and the work itself. But I knew the kind of role I wanted to grow into in the future.

Here we are—September 2025—and reading that back, I almost couldn’t believe it. Because I could have written it today, as an actual description of my job, team, and company. Red Cell, which didn’t yet exist when I wrote that, is an incubator building disruptive technologies (“growing fast and innovating” ✔️). My team is everything I imagined it would be and more ✔️. And while we work really hard, we have fun too ✔️.

I didn’t follow a rigid five-year plan. And I didn’t manifest my future, though I’ve often found that luck is on my side.  But I knew what I wanted, and I worked toward it—even when the next step wasn’t totally clear. (And as it turns out, I made the move to Red Cell’s GC about 18 months after setting out that vision).

So here’s your move: write down your goal. Make it bold, specific, and a little scary. You might look back in five years and realize you nailed it.

2. Break it down into skills rather than steps.

If you know your goal is to land a Deputy GC role, for example, you need to figure out what that actually requires. To do that, you need to think beyond titles and toward capabilities

What do people in those roles know how to do well? What do they get trusted with? What skills, relationships, or experiences are they building? Once you know the skill gaps, you can work on filling them—even before you get the job.

You might:

  • Volunteer for a cross-functional project so you can practice leading outside of legal

  • Shadow a peer who regularly presents to the board

  • Get coaching on how to influence execs when you’re not the one with the final say

Here’s where mentors and sponsors and even one-off networking conversations can come in. Ask them for insight:

  • “If I want to be considered for [role X], what do I need to be known for?”

  • “What would make me an obvious choice in a room I’m not in?”

  • “What do people in [role x] regularly excel at, that I might not have experience with yet?”

Most people are happy to help when you ask a concrete question that shows you’ve thought things through.

3. Say it out loud.

Once you have a goal, tell people.

This one may seem counterintuitive. You’ve probably seen advice not to share your goals—because talking about them gives you a dopamine hit and can trick your brain into feeling like you’ve already accomplished something.

That’s real. But there’s a flip side.

Talking about your goals creates social pressure to follow through. It also increases the odds that someone will help you get there.

From managers finding projects for you to grow your skills and experience, to your network sharing job opportunities that fit your goals, you may be surprised by how much support you get. 

If you have the type of relationship with your current manager where you can share that you want to outgrow your role (even if that means leaving the company), they may be an amazing resource. That was my experience at the Globe and part of what let me hit my goals so soon. My boss knew I wanted to be a GC and worked with me to make sure I had the exposure to be prepared when the time came.

If you don’t say it, people can’t help you. If you do, they just might.

4. Seek regular feedback from the right people.

Many lawyers wait for annual reviews. Don’t.

Seek feedback proactively and strategically. Talk to people who understand what you’re working toward—like a cross-functional leader, a mentor who’s been in your desired role, or a trusted peer who’s seen you operate under pressure.

Try questions like:

  • What do you see as my unique strengths?

  • What am I not yet known for, that I should be?

  • What’s one thing that might be holding me back?

  • What do you think are my blind spots?

Frame your ask around your goal, and you’ll get more meaningful input.

5. Audit your calendar and shift your time.

If your calendar is 95% reactive legal work and only 5% growth, leadership, or strategy—you’re not in control of your next career step. You’re not even fully in control of your day-to-day.

Start with a simple exercise. Pull up your calendar from the last month. Then ask yourself:

  • What percentage of my time is spent doing versus making an impact, and growing?

  • Which tasks could be delegated, automated, or templatized?

  • What would it look like to actually protect time for higher-impact work?

For in-house lawyers, just “doing” often looks like reviewing NDAs, answering quick Slack messages, or redlining the tenth version of a vendor agreement. The work is necessary, but relatively low value to the business.  And none of those activities, by themselves, position you for your next role or to drive real impact.

“Growing” looks different. It might be leading a cross-functional project, preparing a training for the business, mentoring a junior lawyer, or blocking time to really understand an emerging area of law that matters to your company. Sometimes it’s even carving out space to think: What’s the most strategic way for legal to support the business this quarter? Growing type work is more valuable to you and to the company, because it’s where you can drive major impact.

If your audit shows you’re stuck in “doing” mode, you’re not alone. Most of us default there because it’s urgent, visible, and comfortable. But that’s also why you need to intentionally shift your time.

Protecting time is only half the battle; sometimes you also need to raise your hand and ask for the high-impact work.  

And if there isn’t a high-impact project available right now, don’t let that stop you from growing. In both of my last two roles, I carved out time to read full treatises on areas of law that were new to me but critical for being able to operate strategically. It wasn’t glamorous, but it was transformative.

Even one extra hour a week of proactive, strategic work compounds quickly. Block the time. Defend it. Use it well. 

You get to create your own path.

That’s both the gift and challenge of being a mid or senior level attorney. There’s no syllabus anymore. No automatic move up the hierarchy. No professor or partner whose job it is to guide your next step.

It’s all you.

But that also means you get to decide: What kind of work do you want to do? What kind of colleagues do you want around you? What kind of life do you want to build around your career?

No one is handing you the map. The trail is yours to explore. So start small: set a clear goal, break it down into skills, get feedback, and share it. I wrote even more on the topic of proactive growth here, so feel free to check that out too.

Then take the next step. And the next.

You won’t always feel certain. Sometimes you’ll fail, and other times you’ll reach a goal only to realize you don’t want what you worked for.  But if you keep moving with intention, you’ll look up one day and realize you’ve built a career and a life that are unmistakably yours.

That’s it for today.

But before you go, here are a few links I think you will enjoy.

Each week, I share content from across the web that will help make your life as an in-house lawyer better. Let me know your favorite.

  • I was on the How I Lawyer Podcast! - I always enjoy listening to this podcast from my friend, Georgetown Law professor, Jonah Perlin. This time, I got to go on the show as a guest, and it was a fun conversation about non-linear career paths.

  • Is 996 Taking Over San Francisco? - This blog post from Ramp claims Ramp data shows evidence that 996 - the work schedule where people work 9AM to 9PM six days a week, is increasingly popular in San Francisco. Their data is limited to Ramp customers, but I really hope the trends they’re seeing are not indicative of a broader pattern.

  • Untangling Your Self-Worth From Your Career - My take on why it’s essential, especially for in-house lawyers on non-linear career paths.

  • Hold Off Before You Lose Your Sh*t - I was doomscrolling while my flight home was delayed last week and somehow ended up on @dept_of_redundancy_dept’s Reels. A lot of his hyper snarky posts made me laugh. This one is also great advice for lawyers.

  •  Does Work-Life Balance Make You Mediocre? - This piece from Cal Newport responds to a WSJ opinion piece published in July, suggesting that the answer is yes. I prefer Newport’s take.

Thanks for reading! Look out for the next issue in your inbox next Wednesday morning.

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