How to Make Your "Weird" Career Move Your Competitive Advantage as an In-House Lawyer

Deep Dive

Taking a unique professional path can be a competitive advantage - if you’re intentional about it.

I quit my job as a securities litigator to open a juice bar.

It wasn’t intended as a short break from the law. It was a full-on professional pivot.

I left Big Law, signed a commercial lease (and then another), learned about food safety laws and restaurant permitting, hired a team, and started blending green things for money.

And it turned out to be one of the best decisions I ever made—for my legal career.

Seriously.

Years later, when I returned to law, that move was a huge asset. It set me apart. It made me more competitive in a sea of traditional resumes and taught me how to more effectively support the businesses I worked with. And eventually, it helped me land in-house roles that felt tailor-made for the kind of lawyer I’d become: business-minded, practical, fast on my feet. Plus, along the way, I found my professional sweet spot as an in-house lawyer.

Let’s talk about how to do the same with your weird career move.

Why the “Perfect Resume” No Longer Exists

Law school conditions us to think that careers should follow a straight line:

summer associate → associate → partner [maybe with a stint clerking or in government, for good measure]

I know my 10-year plan when I graduated law school included all of the above.

Anything that deviates from that path can feel like a problem needing to be explained away. And many people are inclined to try and brush over or ignore the “weird” aspect of their resume when interviewing.

But in my opinion, that’s a big mistake.

The mindset that legal careers must be linear is outdated. Especially in-house.

And when you behave as though your unique path is a problem, the people you’re talking to assume you’re right.

The best legal departments don’t want cookie-cutter lawyers who think, look, and talk the same. And they don’t need robots (we have AI, now!). Instead, they want lawyers who think like businesspeople. Who understand risk and ambiguity. Who know how to work with non-lawyers. Who’ve seen more than just redlines and time entries.

In that world, your so-called “detour” might be the most valuable thing on your resume. Because it serves as evidence that you’ll likely be capable of giving business-minded advice from day 1.

Plus, if yours is an especially interesting (or just plain weird) path, hiring manager or recruiter curiosity alone may help get you in the door.

Reframing Your Surprising Move

Here’s some of what my time running a juice bar taught me (and how I explained it in interviews):

• Initiative: I had an idea and made it real. That translated directly into how I approached new roles. I didn’t sit around waiting for someone to tell me what to do. Once I understood the goal, I went out and figured out how to make it happen.

• Business acumen: I ran a P&L, negotiated leases, and managed vendor contracts to purchase hundreds of pounds of fruit each week. I understood what it meant to make payroll. Those experiences gave me a clearer sense of how to support a business—not just legally, but operationally.

• Communication: The food service industry is a service industry. You get good at reading the room. The legal industry is a service one too. We might not think about them as being the same, but the learnings from food service apply to lawyers too.

• Perspective: I didn’t just “go in-house”—I’d been the business. So I could think like a business-person, not just advise them. And having hired lots of advisors to support my business, including lawyers, I understood how the most effective experts operated.

I didn’t frame my time running a business as a mistake from which I was recovering. I framed it as an incredible learning opportunity.

That made me stand out.

Plus for me personally, it had been an opportunity to step back from the grueling and sometimes unrewarding world of big law for long enough to realize I like practicing law. I just wanted to do it in a different context.

How to Tell Your Story in Interviews

If you’ve taken time off, switched industries, started a business, or just done something non-traditional—here’s how to turn that story into strength:

• Own the narrative: Don’t apologize. Don’t hedge. And don’t you dare try to skip over it like it didn’t happen. Speak clearly and confidently about what you did and why.

• Draw the throughline: What connects your “weird” move to the role you want now? What did you learn that made you better? For me, I learned to be more business-minded and got extensive experience negotiating contracts. I didn’t negotiate a single contract as a Big Law litigator, and contract negotiation was one of my primary responsibilities for my first in-house job.

• Make it relevant: Talk about the skills and muscles you built that apply to the role you’re interviewing for. There are always connections—find them.

The goal is to sound like someone who made thoughtful moves (whether or not they went exactly as planned), learned from them, and is now bringing a deeper, broader skillset to the table.

But What If That Story Doesn’t Feel Like the Whole Truth?

As lawyers, being truthful and ethical is essential. Full stop.

But sometimes, our commitment to truth gets twisted into a tendency to tell the most negative version of our own stories.

It’s ironic, really.

When we’re advocating for a client—especially as litigators—we’re masters at crafting a compelling narrative from the available facts. We understand that opposing counsel will tell a different story from the same facts. And we also understand that both versions can be true.

But when it comes to ourselves? We forget that skill entirely.

We default to a version that downplays our strengths, centers the hardest moments, and assumes we need to “confess” every challenge to be honest.

We don’t really, though.

Let me show you what I mean with my own story.

When I returned to the law after running Thirst, I could have led with the challenges: Our second location was a headache. Balancing entrepreneurship with full-time caregiving for our infant son was overwhelming (yes, people warned me). The business didn’t make the kind of money I’d hoped.

All true.

But it’s also true that I loved the people, I learned a ton about running a business, and—most importantly—I realized how much I missed thinking like a lawyer. That realization surprised me. It’s what made me want to go back to practicing.

So, which version of that story do you think helped me land my next role?

Both versions are true. But only one frames me as someone you'd want to hire.

You don’t owe anyone the messiest version of your story.

Yes, being truthful is essential. But when you’re looking for a job, the most useful version you can tell - for you and the person you’re talking to - is the one that highlights what you’ve learned, how you’ve grown, and why you’re ready to bring that to the table.

That’s not spin. It’s advocacy.

And if you’re a lawyer, you know all about that.

Remember: Your Career Doesn’t Have to Make Sense to Anyone But You

If you’ve taken a path that looks strange on paper, good for you. Mine does too, and it’s been awesome so far.

Your non-linear career means you were brave enough to make a hard decision, rather than going with the path of least resistance. You chose to chase something. To build something. To walk away when it wasn’t working. Whatever the details, that’s not a liability - it’s being proactive.

And that experience makes you a more effective in-house lawyer.

As a lawyer, you already know how to advocate for others. If you’re on a non-linear career path, you just need to take that same skill and do it for yourself.

If you own the twist in your story and connect the dots clearly, people will take notice. You don’t sound like every other lawyer in the room. That’s exactly the point.

If you’ve taken a non-linear path, I’d love to hear from - how has your unique background made you a more effective in-house lawyer?