We’ve all been there. You wake up one day, pour your coffee, sit down at your desk, open your inbox … and feel absolutely nothing. No excitement. No energy. Just an overwhelming sense of, “Is this really what I’m doing for the next 10, 20, 30 years?”
Could it be more than boredom? Could it be frustration? The industry you once loved is changing, your role isn’t what it used to be, or you feel like you’re putting in more than you’re getting out.
That’s when the thought creeps in: “Maybe it’s time for a change. Maybe I need to pivot.”
But here’s where most people get stuck. Pivoting sounds great in theory, but how do you actually do it without losing your mind (or your paycheck)? How do you make a big leap without landing flat on your face?
The secret? Learn from the people who’ve done it before.
Some of the most successful professionals — whether they’re entrepreneurs, investors, or executives — didn’t just stick to one rigid path. They evolved, pivoted, and found new ways to apply their skills. And they did it without completely starting from scratch.
So if you’re looking for a career shift but aren’t sure where to start, here are the biggest lessons from those who’ve made it work, with added advice from experienced entrepreneur Dr. Tony Jacob.
1. Build Before You Burn
We all love a dramatic exit story. You know, the “I stormed into my boss’s office, threw my resignation letter on the desk, and never looked back” kind of story. It’s bold. It’s cinematic. It’s also a terrible idea.
A successful pivot isn’t about impulsively quitting your job and hoping for the best. It’s about laying the groundwork for what’s next before you make your move.
Think of it like this: If you were moving to a new city, you wouldn’t just sell your house, pack a bag, and show up hoping you’ll find a place to live. You’d research neighborhoods, line up an apartment, maybe even visit first. So why wouldn’t you approach a career change the same way?
That’s the key: Test the waters before you jump in. Too many people make career pivots harder than they need to be by making them an all-or-nothing decision. Instead, ease your way into it, and by the time you’re ready to go all in, you won’t be starting from scratch — you’ll already have momentum.
2. People Matter More Than Products
People get obsessed with the thing — the business idea, the job title, the industry.
Every great opportunity is built around great people. Investors don’t merely back ideas; they back teams. Companies don’t just hire for skills; they hire for culture fit. And entrepreneurs don’t only succeed because of their business model; they succeed because of the relationships they build.
When you’re making a career move, don’t simply focus on the job or the industry. Focus on the people who inspire you. Find the mentors, colleagues, and leaders who get it, and align yourself with them.
Dr. Tony Jacob, who has invested in over 250 different companies, puts it this way: “I’ve noticed that if someone has both high IQ and high [emotional quotient], they tend to succeed. We invest in people, not just ideas. The same is true when you make a career move — look at who you’re working with. If they have big egos and no self-awareness, run the other way.”
Think about that the next time you’re evaluating an opportunity. Who are the actual humans involved? Would you want to work with them? Learn from them? Grow with them? If not, it doesn’t matter how good the opportunity looks on paper — it’s probably not worth your time.
3. Know the Difference Between Fear and Instinct
Fear and instinct are tricky. They both make your heart race. They both make you second-guess yourself. But one is trying to protect you, while the other is trying to hold you back.
Most people don’t make the career move they know they need to because they mistake discomfort for danger. So how do you tell the difference? It’s fairly simple.
Fear says: “This is scary. I might fail.”
Instinct says: “This is exciting, but something feels off about this specific opportunity.”
The key to a successful pivot is knowing when to push through fear and when to listen to your gut. Dr. Tony Jacob shares how he’s learned to balance the two:
“I used to make decisions based purely on gut feeling, but I learned the hard way that gut feeling isn’t always right. Now, I sit with ideas. I let them breathe. I do my due diligence before diving in. A good career move should feel like an informed decision, not a blind leap.”
4. Reinvention Is a Lifelong Game
Most people think of career pivots as a one-time thing. They imagine themselves making the big move — the one that finally lands them in the “perfect” career. But one pivot is never the last one.
The world moves too fast for that. Skills become outdated. Industries shift. Technology changes everything.
The most successful professionals aren’t the ones who found one thing and stuck with it forever. They’re the ones who stay curious, adaptable, and open to change.
Dr. Tony Jacob has seen this play out in his own journey:
“I never thought I’d be where I am today. I was in medicine,” he says. “Then I was running a business. Now I’m an investor. And now I’m thinking about building something totally new. If you think you have it all figured out, you’re already falling behind.”
The smartest thing you can do? Treat your career like an ongoing experiment. Keep learning. Keep evolving. And most importantly, never get so comfortable that you stop growing.
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