Planning a Sabbatical: How to Step Away Without Derailing Your Finances

In today’s fast-moving world, it’s easy to slip into autopilot: pushing through deadlines, chasing the next promotion, and watching RSUs vest quarter after quarter. But more and more tech professionals are realizing that real success isn’t just about climbing higher; it’s about creating space to breathe, reset, and realign with what matters most. It’s no surprise: a recent survey from The Upwork Research Institute found that 58% of tech workers feel overwhelmed by their daily responsibilities and tasks.

That’s where a sabbatical can change everything. Whether you’re stepping back for health reasons, to recover from burnout, to spend time with family, or to explore a new path, time away doesn’t have to mean financial chaos. With the right planning, a sabbatical can be the bridge between where you are now and the more intentional, fulfilling life you want to create.

The Mechanics of Planning a Sabbatical

More employers are beginning to recognize the value of rest and renewal, with companies like Intel, Workday, and Adobe offering paid sabbaticals once employees meet certain service milestones. But not every organization provides this benefit.

If your employer doesn’t offer sabbatical leave, or if you’re treating your break as a bridge to a new career opportunity, it doesn’t mean the idea is off the table. It simply means your financial plan needs to do the heavy lifting.

Here are the key areas to focus on as you prepare:

• Clarify Your Purpose and Timeline. Are you stepping away to recover, spend time with family, or explore a new path? Defining your “why” will help you set the right timeline and determine how much money you’ll need.
• Calculate Your Cash Needs. Map out your essential expenses. Many people create a lean “sabbatical budget” that trims extras, allowing their cash cushion to stretch further.
• Build a Dedicated Cash Reserve. This could come from selling investments, exercising stock options, or saving aggressively in the years before your break. The goal is to avoid dipping into retirement accounts or taking on debt.
• Review Investments and Taxes. A sabbatical can shift your financial picture. Consider how reduced income may affect RSU vesting, tax brackets, and deductions. Some years with lower income may even open doors for tax-smart moves like Roth conversions.
• Protect Your Safety Net. Make sure your health, disability, and life insurance don’t lapse. Options like COBRA, ACA marketplace plans, or spousal coverage can help keep your protection in place while you’re away.
• Stay Flexible. A three-month pause may evolve into a longer reset or even a career change. Building flexibility into your plan means you can adjust without unnecessary stress.

Strategies to Make Your Sabbatical Work

Taking time away from work can feel exciting, and a little intimidating. The key is to approach your sabbatical with the same intention you would bring to any major career or financial decision.

These strategies can help you make the most of your time off while keeping your long-term security intact:

• Practice Living on Your Sabbatical Budget Early. Try out your pared-down spending plan for a few months before your break begins. This not only helps you spot any gaps but also eases the transition into a new rhythm of living.
• Diversify Your Cash Cushion. Instead of relying on one source of funds, consider blending cash savings, proceeds from assets (like RSUs or a property sale), and even some light consulting or contract work. Having multiple streams of support reduces pressure and extends your runway.
• Plan for Your Reentry. Sabbaticals are easier to embrace when you’re confident about what comes next. Think ahead about how you’ll reenter, whether it’s returning to tech, exploring entrepreneurship, or simply having the financial flexibility to choose your next move on your terms.
• Seek Professional Guidance. A financial planner can help you run the numbers, model different scenarios, and identify tax savings opportunities. This helps ensure your sabbatical is backed by strategy, not just hope.
• Reframe Productivity and Identity. Many high-achieving professionals struggle with the idea of “not producing” while on a break. Shifting your mindset from constant output to intentional rest, reflection, and personal growth is just as important as financial preparation. Viewing your sabbatical as an investment in your long-term well-being can help you step away with less guilt and more purpose.

Planning a Sabbatical: Real-Life Stories

Sometimes the clearest way to understand sabbatical planning is through real stories. As a financial planner, I’ve guided clients through the process of transitioning away from demanding tech roles and into new seasons of life.

Below are four examples of tech professionals who took very different approaches to their breaks, but all share a common thread: thoughtful financial planning gave them the freedom to step away with confidence.

Note: The names and certain details in these examples have been changed to protect privacy.

Case Study #1: Emma, From Tech Executive to Small Business Operations Strategist

Background: Emma spent over a decade in a high-paying tech leadership role with substantial RSU compensation. In early 2022, she faced significant health challenges that required a 12-week FMLA leave. Initially, she planned to return. But as her health needs became clearer, she decided to step away from tech entirely.

The Transition: By July 2022, Emma launched her own consulting practice. She made a deliberate choice to slow down, focus on her well-being, and build a business aligned with her values. To support this shift, Emma:

• Sold a property, realizing a substantial gain
• Sold remaining RSUs and other investments to create a multi-year cash cushion
• Significantly reduced spending to match her new priorities

Today: Emma continues to live off the proceeds from her real estate sale and investments while building her consulting practice at a sustainable pace. Her focus has shifted from maximizing income to maximizing health and personal fulfillment, all made possible by early, thoughtful financial planning before her sabbatical.

Case Study #2: Claire, From Tech Leader to Balanced Sole Proprietor

Background: Claire had an impressive career in big tech, holding senior roles with strong base pay and RSU packages. But after years of nonstop work, she began exploring sabbaticals as a way to pause and reassess.

The Transition: In 2021 and again in 2022, Claire took 12-week paid leaves from two different tech employers. While her base salary continued during those leaves, no RSUs vested, resulting in a temporary drop in total income. In 2023, she accepted a C-suite role outside of big tech but quickly realized it wasn’t the right long-term fit. She left after one year and took another full year off to recharge.

Today: Since 2024, Claire has been running her own business as an independent leadership development consultant. She earns at the same level as her peak tech years but now works just 30 hours a week. Her sabbatical planning allowed her to transition smoothly between employment, time off, and entrepreneurship without financial strain.

Case Study #3: James, Four-Year Break to Find the Right Role

Background: James left his high-income role in big tech in 2021 with the goal of taking an extended break to reset and explore new opportunities. He had a clear picture of his spending needs and adjusted his budget before leaving, ensuring he could comfortably live with reduced income.

The Transition: Over the next four years, James did occasional contract work for tech companies, bringing in supplemental income without committing to a full-time role. His careful planning, including a reduced budget and cash reserves, gave him the freedom to wait for the right opportunity rather than rushing back.

Today: James is now in a new role in his field, outside of big tech, with a company that’s a better cultural and lifestyle fit. He credits his financial preparation for giving him the space to step away for multiple years without sacrificing long-term security.

Case Study #4: Ben, From Layoff to Freedom to Choose

Background: Ben left his role in big tech for a smaller employer, seeking a better fit and more manageable pace. But less than two years later, he was unexpectedly laid off. With two small children at home, he had to make a quick decision about his next move.

The Transition: Ben decided to follow his passion, becoming a freelance writer specializing in health and lifestyle. Within 18 months, his income was back to the same level he had earned in tech. While he experienced success as a freelancer, the demands of self-employment alongside raising young kids were intense. During this time, his wife’s career continued to advance, with steady pay increases. When we reevaluated their financial goals and spending plan, it became clear that Ben didn’t need to work unless he wanted to.

Today: Ben pressed pause on his freelance career in 2025 and is taking time to reassess what he wants to do next, with the confidence that his family’s financial plan supports his choices.

Planning a Sabbatical with Confidence

Taking a sabbatical isn’t just an extended vacation. Rather, it’s a chance to step back, reset, and create the space to design the life you truly want to live. For busy professionals in high-pressure industries like tech, an intentional pause can be the difference between running on fumes and coming back renewed.

The stories above share a common thread: sabbaticals are most successful when they’re supported by thoughtful financial planning. With a clear strategy for cash flow, taxes, insurance, and reentry, you can step away knowing your long-term security is intact.

At Simplicity Wealth Management, we’ve guided many high-achieving tech professionals through this process, helping them build a financial cushion, clarify their goals, and shape their time away with purpose. If planning a sabbatical is on your horizon, let’s talk about how you can step back with confidence and return on your own terms. Book a complimentary Simplicity Session today to start the conversation.