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5 tips from successful career switchers

Learn how to switch careers from an engineer turned comedian, a lawyer who became a real estate investor and a jack-of-all-trades who launched a blogging business.

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Have you ever asked yourself whether you’re in the right career? Maybe you got your first job based on a college major you chose when you were a teenager, for example — and now that you’re older, you’ve realized you might be better suited for a different career path or industry. Or maybe you picked a career that isn’t super-compatible with raising a family, and you’d like to find something that would give you more time at home. Maybe you simply want a job that lets you see the world, or lets you be your own boss.

Well, career switches are possible — but they aren’t always easy. You’ll probably have to build some new skills and start seeking out a new network. You might have to go without a paycheck as you transition into your new career, or spend some time working your current full-time job while building up your new career as a side hustle.

I interviewed the following career switchers to learn how they made the big change:

  • Dan Nainan, who transitioned from Intel engineer to stand-up comedian
  • Earl White, who worked as an attorney before co-founding House Heroes, a real estate company
  • Kelan Kline, who went through five career changes before launching personal-finance blog The Savvy Couple with his wife, Brittany.

Read on to learn why they knew it was time to change careers, how they built their new careers, and whether they’re happy they made the switch.

Know when it’s time to make a career change

There’s no one way to know when it’s time to make a career change. In fact, each of our career-changers switched careers for a different reason.

Dan Nainan switched careers after he discovered an unexpected talent as a comedian. “I was a senior engineer with Intel Corporation,” Naiman explained. “My job was to travel the world with the company’s senior executives, doing technical demonstrations on stage at events and I was incredibly nervous about speaking on stage. I took a comedy class to get over the fear, and the comedy kind of took off.”

How far did his career take off? Nainan’s comedy chops have earned praise from people like Apple co-founder Steve Wozniak and former President Barack Obama.

Earl White, meanwhile, was inspired to change careers after a significant life change: Parenthood. “My son was born in March 2017 — and I knew law wouldn’t give me the freedom to be present for my family in the mornings, evenings, and weekends.” He had been investing in real estate part time since 2013 and decided to “take the plunge” into a full-time real estate career.

Kelan Kline had many different careers before The Savvy Couple became his full-time job. “I have personally had more than five career changes after college,” he told me. For a while, he worked as a jail deputy, but after two-and-a-half years the job had started taking a toll on his mental health. So he switched careers and started working as an office manager (taking a significant pay cut) while launching The Savvy Couple as a side hustle. “Nine months later, it started to make money and I quit my job to run our blog full-time.”

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Leverage your current job as much as possible

If you’re going to transition into a new career, do as much of the work as possible while you still have your current job. This might mean taking classes at night or on the weekends, building a network of people in your desired career, or turning your prospective new career into a side hustle.

Kline built The Savvy Couple for nine months before it started earning money. White had four years of real-estate experience before launching his own company. Nainan wanted to pursue comedy in New York without giving up his job at Intel — so he asked the company if he could move.

“I knew I wouldn’t be able to seriously pursue comedy in Silicon Valley,” Nainan explained. “ So I asked for and got promoted to a job in sales in New York City. The company paid every penny of my moving costs, even moving my car to New York.”

If you’re hoping to make your own career transition, do as much work as you can while still keeping your current job. Learn about the career you plan to transition into. Make sure it’s right for you. If you’re planning on becoming a freelancer or an entrepreneur, start a side hustle to see if you like the idea of being your own boss — and if you can make any money.

As White puts it: “We all aren’t in a financial position to quit a well-paying job based purely on speculation. Although you can’t remove all risk, it’s good to at least ‘test the waters’ on your business idea before switching full-time.”

Prepare for the start-up costs of a career switch

It’s a good idea to go into a career switch with the understanding that there may be some start-up costs involved. It also might take some time for your new career to give you the income you need. That said, the people I interviewed said that their career shift had not hurt them financially. In fact, their finances improved.

“I can sometimes command as much as $20,000 for corporate events,” Nainan told me. “What boggles my mind is that it used to take two months working at Intel to make that much money, and now I can sometimes make that in an hour.”

If you end up working for yourself or owning your own business, there’s no limit on the amount of money you could make. “The upside of owning the company is there is no ‘cap’ on my compensation,” White explained.

However, you also need to be prepared to cover the lean times, especially when your new career is just getting started. “We knew that the first couple of months I would have close to zero income coming in,” Kline told me. “Luckily, within two months of quitting my office manager job, I was able to replace my income through freelancing and running our blog. We had saved a nice nest egg of cash to make sure we were not stressed about putting food on the table during this transitional stage.”

Build the life you want

“Starting an online business was the best decision we have ever made,” Kline explained. “I am making more money than we ever thought possible. I get to stay at home with our 8-month daughter each and every day. We get to travel more, spend more time with our families and do the things we love.”

Kline wasn’t the only one who cited more time with family as a benefit of switching careers. White works in the early mornings, makes breakfast for his family, then cleans up and gets back to work — but never past 5 p.m.! “I also work out during the day and control my diet much better when I’m cooking from home and not eating out, so my health is much better.”

Nainan also has more free time thanks to his career switch — plus, he’s gotten to travel the world. “I’ve performed in 28 countries, and of course all of the travel is paid for by my clients.”

If you’re thinking about making a career change, ask yourself what kind of life you’d like to have after you make the career switch. Would you prefer a jet-setting career or a business that gives you enough time to make breakfast for your family every morning? Changing careers without asking yourself if your new career will give you the life you want is a good way to end up switching careers again, after all.

But that’s what it’s all about, in the end — using work to build the life you want. If your career isn’t getting you the life you’d hoped for, it might be time to make a switch.

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Nicole Dieker is a full-time freelance writer. Her work regularly appears on Bankrate, Lifehacker, The Write Life, and numerous other sites. She is the author of Frugal and the Beast: And Other Financial Fairy Tales. This article is sponsored by Haven Life Insurance Agency. Opinions are her own.

Haven Life Insurance Agency offers this as educational only, and the information provided is not written or intended as specific legal advice. Haven Life Insurance Agency does not provide legal advice. Individuals are encouraged to seek advice from their own legal counsel.

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About Nicole Dieker

Nicole Dieker has been a full-time freelance writer since 2012, with a focus on personal finance and habit formation. In addition to Haven Life, her work regularly appears at Lifehacker, Bankrate,, and Vox. Dieker spent five years as a writer and editor for The Billfold, a personal finance blog where people had honest conversations about money, and is the author of Frugal and the Beast: And Other Financial Fairy Tales.

Read more by Nicole Dieker

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Haven Life is a customer-centric life insurance agency that’s backed and wholly owned by Massachusetts Mutual Life Insurance Company (MassMutual). We believe navigating decisions about life insurance, your personal finances and overall wellness can be refreshingly simple.

Our editorial policy

Haven Life is a customer centric life insurance agency that’s backed and wholly owned by Massachusetts Mutual Life Insurance Company (MassMutual). We believe navigating decisions about life insurance, your personal finances and overall wellness can be refreshingly simple.

Our content is created for educational purposes only. Haven Life does not endorse the companies, products, services or strategies discussed here, but we hope they can make your life a little less hard if they are a fit for your situation.

Haven Life is not authorized to give tax, legal or investment advice. This material is not intended to provide, and should not be relied on for tax, legal, or investment advice. Individuals are encouraged to seed advice from their own tax or legal counsel.

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