You’re at a crossroads in your career. The job that once energized you now feels stale. Maybe it’s the environment. Maybe your passions have shifted and you’d find your spark again in a new sector entirely. But the thought of uprooting your daily life — not to mention your stable income — feels daunting.
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Jean Luo knows exactly how you feel. Now the co-founder of Tiger Sisters, she’s gone through major career shifts that have taken her from Wall Street to Silicon Valley. Her own adventures have given her practical insights into managing money and expectations during a career pivot. GOBankingRates caught up with her as part of our Top 100 Money Experts series to get tips on how to keep your cool — and your cash — intact during a major job change.
Get Brutally Honest With Yourself
While leading the Augmented Reality Shopping and Ads Monetization teams at Snapchat, Luo had a so-called “dream job” — executive role, big team, major revenue responsibilities. But toward the end, Luo found herself disengaging.
Instead of panicking, she took stock of the disconnect. It taught her a powerful lesson: “Before you make a big move, get brutally honest about why you’re leaving and what [problem] you’re solving,” Luo said.
She recommends three distinct gut checks to guide your self-inventory:
- Values check: Ask whether your current role — and your next move — align with what you care about most. If the answer is no, you may land in the same emotional place even after a leap.
- Runway check: Do you have the financial and emotional runway for the transition? “Big leaps often cost more — in time, money, and energy — than we expect,” Luo said.
- Support check: Build a small circle of people you trust to give honest feedback and steady emotional support.
“Leaving isn’t just about escaping what’s wrong,” Luo said. “It’s about moving toward something you deeply want to build.”
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Weigh Risks and Rewards — Financial and Emotional
Luo likens a big career shift to investing, where you weigh risk versus return — and where diversification matters. In her 20s, she moved from Goldman Sachs to an entirely new industry — social gaming at Zynga. Later, she left the corporate world to co-found Tiger Sisters.
“In both cases, the financial risk was high, but I looked at upside potential the same way I’d look at a venture investment: asymmetric bets where the upside is transformational and the downside is survivable,” she said.
Changing your job — or even uprooting your career — can cause emotional aftershocks, which Luo says you should acknowledge upfront.
“New jobs or ventures aren’t just exciting; they’re destabilizing. You’re rebuilding identity, routines, even your social fabric,” she said. “I’ve been through this multiple times, and every reinvention brought waves of doubt. What helped was reminding myself: life gets harder before it gets easier. If you expect that dip, you won’t be blindsided by it.”
Take Practical Steps To Protect Your Money
Anytime you make a big leap, you want to make sure your downside is protected — and that holds true for career changes. Luo never advises anyone to jump without a financial parachute.
Before making any changes, build a six- to 12-month runway. “Before I left Snap, I made sure I had enough liquidity to cover expenses and then some,” she said. “It’s the difference between making bold choices and making desperate ones.”
Luo also suggests separating your growth portfolio from your safety net. “I keep high-risk, high-reward investments in one bucket, but I never touch the savings I rely on for stability,” she said. “That discipline let me weather the uncertainty of leaving a steady paycheck.”
Worried about unpredictable income? Luo handled this situation by automating whatever she could. “Even when my income became unpredictable, I kept auto-contributions flowing into index funds and retirement accounts,” she said. “Continuity matters more than timing.”
Make Healthy Changes to Your Mindset
Starting over in your career can bring up intense emotions — sometimes even feelings of failure. Luo reframes those feelings to emphasize the positive: “Starting over isn’t failure; it’s power,” she said. “I’ve started over at 25, 35 and beyond — from finance to tech, from tech to media. Each time, the most useful reframe was, ‘This isn’t me losing something; it’s me choosing growth.'”
She uses simple tools to shift her perspective, like writing a letter to her “future self” five years down the line. “It helps you see the courage behind your decision instead of just the fear,” she said.
Even small tweaks to how you describe your job change can affect your mindset. Instead of saying, “I’m trying a new career,” introduce yourself as a founder or creator. Owning your new identity makes the transition feel more like a deliberate transformation than a tentative trial run.
If the prospect of switching jobs or careers still scares you, Luo reminds you that you don’t have to blow up your life to move forward.
“Sometimes one small action — meeting a mentor, setting up a side project — is enough to build momentum and remind yourself you’re moving forward,” she said. “At the end of the day, you can protect your finances with discipline — but you protect your potential with mindset.”
This article is part of GOBankingRates’ Top 100 Money Experts series, where we spotlight expert answers to the biggest financial questions Americans are asking. Have a question of your own? Share it on our hub — and you’ll be entered for a chance to win $500.
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This article originally appeared on GOBankingRates.com: Hate Your Job? Here’s How To Switch Without Losing Your Mind — or Your Money
