If You’re Not Reinventing Yourself, You’re Falling Behind! Here’s What To Do

Reinvention is the secret weapon of high performers.

Most careers follow a predictable script. You start at the bottom, climb the ranks, and eventually settle into something resembling stability. But the people who make the biggest impact, the ones who don’t just play the game but change it, break that script. They evolve. They shift. They reinvent.

I know because I had to. Multiple times.

The First Shift: From Enabler to Builder

Early in my career, I was what I call an “arms dealer.” I sold internet access equipment; routers, switches, and modems to ISPs who were, in turn, providing consumers with the internet itself. I was deep in the infrastructure layer, supplying the technology that powered the dot-com boom.

But over time, I realized something: I was always enabling someone else’s business, never building my own.

That realization pushed me to take a risk. I wanted to move beyond selling the parts and start building the whole thing. I wanted to create a product, shape a market, and drive something forward from scratch. So I made the leap and joined Trapeze Networks.

Entering the Startup World

Trapeze was a Wi-Fi startup when enterprise Wi-Fi was still in its infancy. It was a chance to be at the forefront of something new, to apply everything I’d learned about networking in a totally different way. Instead of selling infrastructure to ISPs, I was now helping businesses build seamless, secure wireless networks.

The market was taking off, and we had the right team at the right time. I stepped into go-to-market strategy, worked with our sales channels, and pushed to make Trapeze a player in this emerging space. I wasn’t just selling, I was shaping the strategy for an entire category.

That experience opened my eyes to something bigger. I saw how a startup came together from the ground up, how funding worked, and how product decisions were made. I was still on the business side, but I was getting closer to the core of it, closer to being the one actually building something.

The Leap to Founder

That’s when I knew it was time to make the leap for real.

I left Trapeze to start my own company, Ooma. The idea was simple but disruptive: What if phone calls could be free by leveraging the power of the internet? At the time, long-distance calls still cost real money, and Ooma aimed to eliminate that entirely.

It was my first time as a founder, and everything was different. Suddenly, I wasn’t just responsible for sales and partnerships, I was responsible for the whole thing. Fundraising, hiring, product vision, making sure we didn’t run out of money. It was a whole new level of ownership.

Ooma was a bold swing, but it was also a crash course in the realities of building a company. The market was shifting; flat-rate mobile plans were emerging, and our value proposition was starting to erode. We had momentum, but we also had growing pains. I had to navigate investor dynamics, internal challenges, and the pressure of keeping everything moving forward.

Learning to Pivot

When my time at Ooma came to an end, I knew one thing for sure: I wasn’t done building.

I co-founded Jangl (originally called Buzzage), a service that allowed people to call and text each other without revealing their actual phone numbers. It was privacy before privacy was a mainstream concern, and it took off fast. We grew to 80 million accounts, which was great, but growth at that pace brings its own set of challenges.

Some investors wanted us to go all-in on enterprise SaaS. Others wanted us to stay focused on consumer adoption. Different visions. Different priorities. And the inevitable pressure that comes when the stakes get higher.

That’s when I learned something important: Reinvention isn’t just about jumping from one career path to another. Sometimes, reinvention means making a hard pivot inside the thing you’ve already built.

We adjusted our go-to-market strategy. We refined the product. We navigated the challenges. But ultimately, we faced the reality that even when you’re building something innovative, the market moves fast. And if you’re not positioned exactly right, you can end up fighting uphill battles.

Recognizing the Signs of Reinvention

Through all these transitions, I started recognizing the signals that tell you when it’s time for a reinvention.

Here’s what I learned to look out for:

1. Boredom – If what used to challenge you now feels easy or repetitive, you’re probably ready for something new.
2. Frustration – This isn’t frustration at just the day-to-day headaches of any job, but a deeper sense that you’re not working on the right problem.
3. Pull – If there’s something that keeps popping into your mind, a problem you can’t stop thinking about, an idea that excites you more than whatever’s on your to-do list. That’s the one that usually matters most.

Reinvention Is a Process

I’ve learned that reinvention doesn’t happen in a single moment. It’s not like quitting one job and starting another. It’s a process of testing, learning, and deciding what’s worth doubling down on. It’s about recognizing when to shift gears before circumstances force you to.

Here’s what no one tells you about reinventing yourself: It’s not always comfortable, but it’s always necessary.

The skills that got you to one level won’t necessarily get you to the next. The opportunities that seemed perfect five years ago might not be relevant anymore. The market doesn’t care about what you’ve done, it cares about what you can do next.

The Only Way Forward Is Through

Looking back, every major leap in my career started with a reinvention. From sales to startups. From hardware to software. From enterprise to consumer. Every time, the same rules applied: old playbooks stop working, new opportunities look risky, and the only way forward is through.

Reinvention isn’t optional if you want to keep growing. It’s the only way to stay ahead, to stay relevant, and to keep playing at the highest level.

So the real question is: What’s your next reinvention?