Ever find yourself daydreaming about how your life might be different had you chosen a different career path?
Or do you ever look at a coworker and think, “I can totally do that job!”
What snaps you back into reality is the voice inside your head that says, “It’s too late — you should've done that after college.”
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Get started with a free financial assessment.
Think again, negative Nancy: Switching careers isn't the risky move it once was.
According to research from LinkedIn, companies ranging from network security to investment banking to staffing services are actively hiring from outside their industries.
That said, changing course usually requires more than a revamp of your résumé. You may need additional schooling, or you might have to accept a more junior position at a time when you should be at the height of your first career.
But it’s not impossible to pull off. In fact, we’ve rounded up three people who successfully took the plunge into completely different professions post-30.
Although they all had unique reasons for their personal transformations, each story has a common thread: It’s never too late — and you’re never too crazy — to make a career about-face.
Who: Jane Whang, Hanover, Maryland
My Career About-Face: "I used to teach eighth grade science at an inner-city charter school, and during one summer break, I decided to take post-baccalaureate science classes to get credentialed to teach at the high school level.
I found it so enjoyable that it inspired me to go back to school to do something in the medical field. My initial thought was med school, but with dentistry I knew I would spend less time in residency and have better work-life balance.
As a teacher I never had that — when I wasn’t teaching, I was grading homework, preparing lessons or completing report cards.
So I decided to go to dental school, which meant four years of being a full-time student again. With no savings from my teacher's salary, I had to rely on student loans and a part-time receptionist job. I also gave up eating out, shopping and traveling so I could make ends meet and stay clear of credit card debt.
I graduated at 33, and currently work in a dental office in the Baltimore area — and am very happy with my career change.
I pursued teaching because I wanted to make a difference, but I couldn’t really see the impact I was making. It was emotionally taxing, and sometimes I felt more like a disciplinarian than a teacher. With dentistry I see immediate results.
"I did have to take on six figures in student loans. But I knew I'd make more money, so it was worth it to me."
The Financial About-Face: To be honest, being a student didn't require a huge financial adjustment after living on a teacher's salary.
I did have to take on six figures in student loans — on top of what I’d already borrowed to get my graduate degree in education. But I knew I'd make more money later, so it was worth it to me.
When I was a teacher, I stressed about how I would ever be able to pay off my grad-school loans. I had very little spending money; couldn’t save; and mostly got by because I lived with my brother, who paid a greater share of the rent.
Now my income is about five times what I was making as a teacher. I still have dental school debt — my monthly payment is equal to some people’s monthly incomes! But I’ve paid off my grad school loans, and I am able to save and live comfortably — in a home that I own.
Why It Was Worth It: Yes, choosing dentistry out of undergrad would have been easier, but I don’t think I would have appreciated it as much back then.
Being a teacher helped me become more emotionally resilient and confident. And I’m able to use skills from both careers to give back: I tutor Baltimore city children, mentor a foster child, and I've gone on medical missions trips to fix dental issues for people in remote parts of the world.
If I had chosen dentistry first, I may have wondered whether teaching would be more fulfilling. But now I can say that I have no regrets or thoughts of 'What if?' "
The Military Officer-Turned Real-Estate-Investor
Who: Kirby Atwell, Frankfort, Illinois
My Career About-Face: "I went to the West Point Military Academy out of high school, and after graduating, I became a second lieutenant in the U.S. Army.
I spent six years in active duty, eventually becoming a captain and commander of a homeland defense site in Shariki, Japan.
I always loved the idea of serving, but I noticed that promotions occurred at generally the same rate. I saw superstars promoted at the same time as peers who did the minimum to get by — which killed the motivation of the ambitious people.
While in the Army, I had started taking online MBA courses, and since I'd always had an entrepreneurial itch, I decided to leave to start a real estate company.
It was a huge adjustment, and at times I doubted my decision to take this plunge. But because I had gone all in with both my time and money, there was no turning back — which, fortunately, forced me to stick it out.
With two partners I started a business, iCandyHomes, which buys distressed properties to rehab and sell. In three years, we’ve grown our team to 20 people and are rehabbing about 26 homes — but our goal is to grow the company much further.
"Within six months, I’d gone from being an Army captain to living in my parents’ basement, struggling to get my first few deals done while going to school full-time."
The Financial About-Face: When I got home from Japan, I hit the ground running — the day after I arrived, I already had appointments to see homes. I also went back to school full-time to finish my MBA.
But I had been naïve about what it would take to get the business going. I had underestimated the startup expenses, including home-office overhead and real-estate seminars that cost in the tens of thousands of dollars.
I also wasn't prepared for the timeline required to start making money — my first deal took nine months to complete.
This was a humbling period for me. Within months I’d gone from being an Army captain to living in my parents’ basement, struggling to get my first few deals done. And while I’d always been a conservative spender, it was still hard to go from having a predictable military paycheck to having no income.
Every bit of money I'd saved, and any money I made on real estate deals just went back into more deals, so I never knew when — or if — I'd have income. I lived with my parents for over a year, and had to take out a small student loan in the second year of school to help cover costs.
But just a few years later, a lot has changed. My partners and I have grown our company enough that I can draw a pretty consistent personal income, although I keep it comparable to my Army captain’s salary. I would rather reinvest the earnings back into the company to build its long-term future.
And here’s one benefit to being a real estate investor: I live in one of our rehabbed properties — a big lifestyle upgrade from my parents’ basement!
Why It Was Worth It: In this industry, you can go from feeling rich to broke in the same day. But I love the challenge of owning my own business.
Plus, I love knowing that our team is directly rewarded based on our results, rather than on an arbitrary evaluation process. We’ve come a long way, and this keeps everyone — myself included — motivated to keep going."
The Media Exec-Turned-Goat Farmer
Who: Brent Ridge, 41, Sharon Springs, New York
My Career About-Face: "My partner, Josh, and I became farmers out of necessity.
We were both successful New York City professionals. Josh was a partner at a boutique ad agency, and I was a doctor turned executive who headed up the health and wellness program at a major media company.
Back then the future seemed limitless for us, so we used all of our savings to buy a vacant, historic farm known as the Beekman Mansion in rural upstate New York. It was meant to be a weekend home, but then Josh and I lost our jobs within a month of each other — and went from having six-figure jobs to zero income within 30 days.
Faced with a million-dollar mortgage, we realized we had to make the farm work for us. A neighboring down-on-his-luck farmer happened to approach us looking for a place to raise his herd of 80 goats. We ended up making and selling cheese and soap from the goat’s milk — and thus began our farming life.
Neighbors and local farmers taught us the ropes. We learned it took a lot of patience to really plant a harvest you can live off. And the first time we saw goats give birth, it felt like watching clowns come out of those tiny clown cars!
Now we grow almost all of our own food and sell goods made by us and other fellow artisans — from goat's milk hot fudge to furniture made from reclaimed barn wood. We also sell our products online and through other retailers, and have written cookbooks, like our latest The Beekman 1802 Heirloom Vegetable Cookbook.
"Every recipe we create starts with what we are harvesting. The origin of every product we design is based on how we personally would use it."
The farming we had to do out of need is now a lifestyle brand called Beekman 1802. And we're happier now than we have ever been in our lives.
The Financial About-Face: We sacrificed a lot so we wouldn't lose the farm. Josh and I had to live mostly apart while he worked another job back in the ad world as I started building the farm.
We used that income to support us during the early years. We didn't want to take out loans and get into debt, so we vowed to grow the business only at a rate we could personally support.
Even though Beekman 1802 is a well-known brand today, Josh and I still do not pay ourselves a salary. Most of our business income goes back into running the farm, our retail operations and our e-commerce site.
We make it work by raising our own food, limiting travel to business trips only, and turning our pursuit of the simpler things in life into a source of content that inspires us and others.
Why It Was Worth It: Everything we do on our farm is because we are passionate about it. Every recipe we create starts with what we are harvesting on the farm. The origin of every product we design is based on how we personally would use it.
For example, one of our most popular items is our Iron Block Branch Vase. It came about because we wanted to display the heavy flowering branches from our fruit trees, and then asked a local blacksmith to design the vessel for us.
Yes, there are struggles and sacrifices that continue, but we are a lifestyle brand because Beekman 1802 is our life. And we wouldn't have it any other way."