What to Consider Before Leaving Your Tech Job

July 31, 2026 | By Jessica Goedtel, CFP®

You’re burnt out, tired, overworked. Maybe even a little disillusioned. You’re ready to get out of your tech role, or even the whole industry.

First off, good job taking care of yourself. Tech money is great, but not at the cost of your mental health. But before you go, make sure you leave on the best financial foot you can. Here are some things to consider as you make the leap.

 

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What’s Your Next Step?

Before jumping ship, have an idea of the next boat you’re boarding. Most people I talk to are doing one of three things:

• Looking for a similar job with similar pay
• Taking a sabbatical before looking for a similar job with similar pay
• Transitioning to a lower paying job/getting out of tech altogether

The first one is obviously a bit easier but still comes with some financial considerations. The other two will require some extra preparation (hey, great time to call a financial planner!).

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Take Inventory – Savings and Cash Flow

Review how much you have in savings (not investments! Let’s try to leave those alone). Money in the bank is going to be critical, especially if you’re taking time off. Do you have enough cash in savings for a sabbatical or extended unemployment?

Next up, review your cash flow. What expenses can you adjust or reduce? Map out a new budget to see if these changes are doable. Will this represent a dramatic lifestyle shift for you? It might be easy to commit to now, but big expense cuts are tough in practice. Consider adjusting now and trying them for a few months before leaving your job.

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Review your Equity Compensation

If you’re in tech, more than likely you’ve got some form of equity compensation. This should be a big factor to review as you transition. Each type of equity compensation has different considerations.

RSUs/Restricted stock. When is your next big vest? When you leave the company, any future vests will be forfeited. So if you’ve got two more weeks before your next tranche hits, it might be worth waiting a bit longer to hand in your resignation.

Stock Options. Whether you have ISOs (incentive stock options) or NQSOs (non-qualified stock options), you’ve got a few things to do before you leave.

• Review your options to see if you have any vested but unexercised options. Take note of the grant price (also called exercise price).
• Review your stock option agreement to see what your exercise window is post-termination. Most plans will allow you a set time after you leave to exercise your options. Read the documents carefully. (Quick side note on ISOs – even if they give you a longer time frame to exercise, ISO rules say you must exercise the shares within 90 days, otherwise they will convert to NQSOs).
• Decide if you are going to exercise shares. What you do here depends on whether you have ISOs or NQSOs.
  1. With NQSOs, you’ll likely want to do a cashless exercise if the stock is “above water” – meaning the stock is worth more than the grant/exercise price.
  2. With ISOs, there’s a bunch of factors to consider. You should really, really consider calling a financial planner in this case. ISO rules are complex and can make a real mess of your finances if handled incorrectly.

ESPP. If you’re currently enrolled in your ESPP plan, you’ll likely be refunded any money you’ve contributed since the last stock purchase.

Whatever type of equity comp you have, it’s worth considering selling available stock to fund your transition. I know I said to leave investments alone, but company stock is different. That’s a lot of exposure tied to one company.

A final note regardless of stock plan type: consider your trading window if you’re subject to blackouts. Leaving the company doesn’t mean that you’ll be able to trade like non-employees.

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Health Insurance

I’m not sure if you’ve heard, but health insurance is crazy expensive right now. If you’re lucky, you’ve been at a job that covers most or all your insurance premiums. But not every employer will do this. When accepting a new job offer, compare your potential employer’s coverage to what you have now. It still might be worth taking a new role even if insurance costs are higher, but make sure you factor it in your cash flow.

If you’re planning to take time off first, you’ll be eligible for COBRA coverage. COBRA lets you stay on your work plan for 18 months if you quit your job. However, you’ll be responsible for paying the entire premium, which includes the amount your employer was subsidizing plus a 2% administrative fee in many cases.

To get an idea of the costs before you resign, look at your most recent open enrollment documents. Employers usually put how much they are paying towards your premiums on the healthcare costs page. You can also check your pay stub for employer paid health insurance premiums.

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401k vesting

Tech companies aren’t known for their stellar 401k matches. But most do match your contributions at least a little bit. Like your stock compensation, the matching funds are almost always subject to a vesting period. Sometimes it’s a year, other times it’s a percentage each year.

To find the vesting schedule, look in your 401k’s Summary Plan Description (SPD). Your 401k custodian should have this. When logging into your account, note how much of your account is employee contributions versus employer contributions. The employee part is always yours, but you’ll need to apply the vesting schedule to the employer portion. For example, if the employer contribution is $10,000 and you are only 20% vested, then you will only keep $2,000 when you leave. You still may decide to walk away, but at least you’ll know how much you’re leaving behind.

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A few other items

Certain things, like sign-on bonuses and education reimbursements, can be clawed back if you leave too quickly. Check your offer letter and your employee handbook for details. Also look for details on how unused paid time off is handled while you’re there – some companies will pay out accrued time, but some are use-it-or-lose-it. A few states, like California and Colorado, require accrued time to be paid out.

I know what it’s like to feel burned out and needing a career shift. It’s a big reason I became a financial planner. I’d love to help you make a career pivot, so if you’re ready schedule a free, no-pressure introductory call with me today.