The Strategic Career Exit: How to Graduate from High-Stress Roles to Sustainable High Earning

As Senior VP & Wealth Advisor at Compound, Jonny Jonson has 12+ years of wealth management and accounting experience. He specializes in serving high-net worth families, tech employees, executives, and busy professionals. He’s helped his clients in Big Tech transition from high-pressure roles to more sustainable lifestyles while meeting their financial goals.

So, you’re burned out. 

But you took a high-stress job for a reason: to grow your career, to earn more money. 

Leaving isn’t so easy. 

But there’s a way to get out without sacrificing all the gains you’ve made. There’s even an optimal transition window for the best exit — with financial stability and less stress. 

Think about your career in three phases: 

1. The grind phase (generally years 1-10) 
2. The transition phase
3. The sustainable high-earning phase 

You can’t wait too long to get out of a high-stress environment: you'll either burn out before you can capitalize on your experience or take a bigger pay cut, because you thought you had to choose between money and life balance. 

Today, we’re sharing a framework for leveraging your hard-earned Big Tech experience to transition into a sustainable, high-paying role with better work-life balance.

Breaking Out of the Mold

Usually, people say you have to choose between a great paycheck and work-life balance.

That means hard workers get stuck running on the hamster wheel. Either they run themselves until they’re fully out of steam, or they hop off and into a much lower-paying job (so they can breathe for once).

But if you strategically time your career transition around a financial cushion — that you build intentionally during your “grind phase” — you’ll have the freedom to find a sustainable, well-paying job.  

Across the tech ecosystem, you can make a lateral move. For example: 

• Big Tech to mid-size moves might look like Meta/Google → Zillow, Yelp, Expedia, HubSpot
• Startup founders moving from high-growth startup → advisory roles or sustainable ventures
• High-stress IC roles like principal engineer at a FAANG → staff engineer at a growth company
• Executive roles like VP at a unicorn → C-level at mid-size tech companies
  

Today’s Career Advice Ignores Better, Off-the-Beaten-Path Opportunities 

You’ve probably been told that high-stress, high-pay jobs are permanent career destinations instead of the training grounds for better (calmer) opportunities.

Often people who’ve been in Big Tech for a long time get the gut feeling, “I need to go to a smaller company where it’s not as intense and crazy of a culture.” And they don’t realize their Big Tech experience makes them an asset to those organizations. 

A career transition doesn’t mean taking a step down in compensation or influence. Instead, use your experience in a high-stress environment to drive significant impact at a smaller tech company. 

During your optimal transition window (Phase 2), your Big Tech experience becomes invaluable to smaller companies. And there’s a pattern to keep an eye on so you can figure out when that is. 

The 3-Phase Career Maturation Strategy

Phase 1: The Grind Phase (Years 1-10)

The grind is necessary. When you start off in Big Tech, lock in for a high-intensity, high-learning period: Prioritize skill development and grow your wealth aggressively during this period. You’re building both your financial base and the professional credibility that will make you a great job candidate later.

Focus on saving around 20% of your income every year — it’ll be a huge asset for Future You if you want to retire around 60-65. Don’t buy a second home or spend excessively. 

It’ll be higher-stress for a while, but the learning and earning acceleration pays well in the long term — whether you want to 1) continue grinding and retire early or 2) take your foot off the gas and smell the roses.

After you’ve been grinding for the better part of a decade and you’re ready to make a move, you’ll have enough experience and money saved.

Phase 2: The Transition Phase

Now, it’s time to test new opportunities and start your career transition. You’re going to leverage your “grind phrase” experience to reach those smaller companies that many tech professionals overlook.

Of course, six years isn’t a one-size-fits-all term. Clock your optimal transition window. First, try to incorporate a trial period: Maybe you ask for a sabbatical, or for short-term disability.

You can also test out the life change through consulting projects, or reduced hours before making a permanent move. And with your accumulated savings, you can stay flexible during this period. 

Treat this as a "two-way door" rather than a permanent, irreversible decision. Most of the time, a career transition will come with some ramifications — not permanent consequences. If you keep this in mind, you can feel more confident deciding when and how to transition to a smaller company that fits the life you want.

Phase 3: The Sustainable High-Earning Phase 

Your “grind phase” experience = your competitive advantage at companies that offer better work-life balance and good pay, too. 

Here’s some great news: Your aggressive saving earlier means you can now prioritize non-financial goals without compromising your long-term security. You can make more values-driven choices based on your family and life goals. 

As you adjust to your new normal, don't let the gravitational pull of the grind phase pull you back. With the right planning and financial cushion, you can afford the wiggle room. 

In the Compound dashboard, you'll be able to see your full financial picture — including how much you have set aside for retirement and for spending today. And we're always here to have a conversation to help plan for your life goals.

How Moves You Make Today Will Pay Off Later 

High earners are recognizing more and more that high-stress roles are training grounds, not permanent careers. Executives are burning out and moving on to fractional work, consulting, or advising. Or they’re taking on less “shiny” roles that give them greater agency in shaping a high-growth company with more time back. That’s time they can spend with their family. 

Competition will grow for the companies that offer more sustainable career paths. Early on in your grind phase? Think about your future transition and sustainable high earning phase. In the end, proactive planning will make a world of difference. The bigger financial base you can build early on, the more options you have later in life as your life evolves and values change.

And if you’re ready to get your finances in order for the big move, my door is always open for a conversation to see how I can help.

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Curious if you’ve got a financial cushion to start making a career transition? Sign up for the Compound dashboard to see your entire financial picture in one place and make your game plan.