It’s a wild time to change careers, whether by your own choice or by surprise. Lately, more people are pivoting, sometimes to chase new dreams, sometimes to keep up with shifting industries. If you’re staring down a fork in your professional road, one thing’s for sure: your finances need a tune-up first. I want to share some of the lesser-known steps I consider essential before making this leap—ones I’ve seen work firsthand and in the stories of folks around me.

How long could you last if your paycheck stopped today? Most of us have heard about the classic six-month safety net, but let’s get real. In a career shift, especially an unplanned one, six months often isn’t enough. Hiring cycles are unpredictable, onboarding takes time, and sometimes finding that “right fit” role stretches far longer than expected. This is why I urge you to stretch your emergency fund to nine months of living expenses.

Before you roll your eyes at the math, recognize that this isn’t just about rent and groceries. Think about insurance premiums, prescriptions, and all those little school fees for the kids—leave nothing out. I’ve worked with people caught mid-transition when a car repair or dental emergency cropped up. The extra three months saved them from panic and bad debt. The truth is, a bigger cushion means better negotiating power and less desperation if the search drags on.

“Do not save what is left after spending; instead spend what is left after saving.” —Warren Buffett

If your career change is on the horizon, start building this fund 12 or even 18 months ahead of time. Channel bonuses, tax refunds, or that cash you find in your coat pocket. Little additions add up, and the peace it brings? Priceless.

Here’s a question for you: What’s your plan for your 401(k) when you change jobs? If your answer is “I’ll just leave it there,” let’s rethink that. Many people forget that letting retirement money sit in a previous employer’s account means less control. Some plans charge higher fees, limit your investment choices, or even freeze certain transactions. Rolling over your 401(k) into an IRA can open up more investment options, simplify your financial life, and avoid costly penalties.

Here’s what I wish more people knew: You generally have a 60-day window to move those funds, or the IRS could smack you with taxes and early withdrawal penalties. I’ve seen this mistake cost clients thousands they never anticipated. The smartest move? Call your plan’s customer service. Ask about direct rollovers—they’ll send the money straight to your new IRA, so it never touches your hands and triggers unexpected taxes.

How much time have you really spent reading those 401(k) plan termination letters? They’re easy to ignore, especially with the mental load of a job change, but missing those details can be costly. Take a Saturday, pour a cup of something strong, and tackle it.

Let’s talk healthcare. Losing employer-subsidized coverage is a big deal, especially if your transition includes time off or starting your own gig. COBRA is the standard fallback, but sticker shock is real: coverage can easily top $700 a month for families. I always encourage people not to just default to COBRA. Compare it to options on the marketplace, and check whether your spouse’s or partner’s employer plan is open to new enrollments due to your qualifying event.

What’s often overlooked is timing. Even a one-day gap can cause headaches. If you’re leaving your job, see if you can negotiate your last day so your coverage extends until the end of the month—it’s a tiny detail that might buy a few extra weeks of protection. Call your HR department and ask detailed questions. Can unused vacation days extend your benefits? Are there lesser-known resources, like telehealth, you can use even after you leave?

“The greatest wealth is health.” —Virgil

Sometimes, a planned break between jobs sounds tempting—time to recharge, upskill, maybe travel. But what about medical emergencies or ongoing prescriptions? I’ve known clients who only learned their medication would cost four times as much after leaving work. Ask your doctor for 90-day scripts before your insurance runs out. Small steps can save big headaches.

Now, what about investing in yourself? Picking up new skills isn’t just admirable—it’s often essential. But not every course or bootcamp is worth the price. When looking at certificates, bootcamps, or even degree programs, focus on the numbers: What’s the upfront cost, and what’s the projected salary bump in your new field? Some coding bootcamps quote $15,000 for tuition but graduates may not see the six-figure payoff promised in marketing brochures.

Have you ever calculated the true “payback period” for skill investments? I suggest mapping out the costs (including lost income if you’re not working), then projecting how long it will take before the new salary makes up for that outlay. Sometimes, a series of smaller online courses with project work yields similar job prospects for less money. Can you get an employer to contribute, even partially, to your upskilling? Never hesitate to negotiate tuition reimbursement in your next offer, especially if you’re moving to a field where your education directly benefits your new team.

“An investment in knowledge pays the best interest.” —Benjamin Franklin

Don’t overlook the network you build through learning, either. In many fields, your classmates and instructors are as valuable as the certificate you’ll earn. Treat every course like a networking event as much as a classroom.

Let me ask, have you started a side hustle yet—or at least tested one? The gig economy isn’t just for deliverers and rideshares anymore. During a career shift, a side gig can bridge the income gap and help you test-drive new skills. I recommend building something sustainable while you’re still employed: freelance projects, consulting, tutoring, or remote contract work.

Set a realistic target: aim for your side hustle to cover at least 30% of your previous monthly income. This buffer isn’t just about paying the bills—it also gives you something to show future employers (or clients) that you’re entrepreneurial and adaptable. Plus, if the new field isn’t all it’s cracked up to be, having extra options already in play brings massive peace of mind.

Have you ever thought about setting measurable goals for your side hustle? Try this: track your income, client growth, and time spent. If after three months you’re not seeing progress, reassess. Is it the market, your approach, or something else? Sometimes, a pivot within your side gig makes all the difference.

“If you don’t find a way to make money while you sleep, you will work until you die.” —Warren Buffett

Transition can be stressful, but also ripe with opportunity. One tip that’s missed by so many is negotiating with your new employer for transitional help. Signing bonuses aren’t just for executives. Many companies offer relocation allowances, temporary housing stipends, or even coverage of benefits gaps if you ask—especially in competitive sectors. Bring these possibilities up in your negotiations; you lose nothing by asking, and sometimes you get a significant bump.

Another little-known tactic: before your last day, talk to HR about accrued benefits. Depending on your employer’s policies, you may be owed severance, unused vacation payouts, extended insurance, or bonus eligibility. Understanding these timelines ensures you’re not leaving money on the table.

One final question: do you have a plan if the transition takes longer than expected? Prepare for emotional and logistical bumps. Stay in touch with industry contacts, build weekly routines for job searching, and schedule regular financial check-ins with yourself. Momentum is easier to maintain if you treat this period like a temporary job of its own.

A career change may always involve uncertainty, but you have more control than you think. By expanding your emergency fund, making wise moves with retirement accounts, managing healthcare gaps, carefully evaluating upskilling ROI, and launching a side income stream, you’re stacking the odds in your favor.

“Change is the law of life. And those who look only to the past or present are certain to miss the future.” —John F. Kennedy

Are you ready to take the next step? The decisions you make today can empower your future self—no matter which path unfolds next.