By Bryan Trugman, CFP®
The corner office. The strategic decisions. The weight of leadership. There are so many pivotal moments in an executive’s career, but few are as critical to your financial stability as changing jobs. You’re evaluating new opportunities, negotiating complex agreements, and planning the next phase of your career.
But are you also giving your personal finances the strategic attention they deserve? Let’s make sure you’re on the right track.
This article provides a blueprint for an executive’s job transition, including samples of essential financial questions and suggestions to address at each stage.
The Exit Strategy: Decoding Your Departure Package
Before you pack up your office belongings, meticulously scrutinize your departure package. It’s a vital step in understanding how your job transition affects your finances.
- Severance agreement: Do a deep dive of your severance agreement. Understand the timetable, the payout structure, but more importantly, know what rights you may be giving up. These are legal documents, and signing one could limit your future options. Kenneth Katz, an employment attorney with KatzMelinger, explains, “When you sign a severance agreement, you are giving up your right to sue and could be walking away with less than what’s fair. It is critical to protect your rights and your worth; get legal advice before signing any severance agreements.”
- Equity compensation: Equity compensation is typically a sizable portion of the wealth of many executives, so it’s important to understand the vesting schedules of your stock options, RSUs, or other equity grants. What happens to unvested shares? What are the vested option exercise deadlines? Ignoring these details can lead to unexpected tax responsibilities or significant amounts of money being left on the table.
- Retirement accounts: Seriously consider your pension, 401(k), and other retirement programs. What are your options? Should you take a payout (which could have significant tax ramifications and penalties), roll your funds into an IRA or your new employer’s plan, or leave them in the current plan (if allowed)? The tax-smart option here is usually a direct rollover, which keeps your tax-advantaged growth intact.
- Healthcare and COBRA: Losing health insurance provided by your work can be a significant worry, and often requires an urgent attitude. Take the necessary steps to navigate your options. Understand the duration and cost of COBRA coverage. Explore alternative choices like your spouse’s plan or the healthcare marketplace. Don’t let a gap in coverage lead to unanticipated medical expenses.
- Additional perks: Don’t forget about things like deferred compensation programs, disability insurance, and life insurance. What options do you have for portability or continuation? Understanding these details can provide a comprehensive financial shield during and after your transition.
Laying the Foundation: Financial First Steps in Your New Role
As you transition into your new role, establishing a solid financial foundation is necessary for long-term confidence and growth. Here’s how to build a strong monetary base that’s aligned with your new position:
- Comprehensive compensation: Your new salary is only one piece of the pie. You need to have a thorough conversation about signing bonuses, equity grants (and when they vest), and other perks. Understand the performance metrics tied to bonuses and the long-term value of equity. Essentially, negotiate with a holistic view of your compensation (and a confident attitude!).
- New benefits: Thoroughly examine your new employer’s life insurance, disability insurance, retirement plans (pay particular attention to company matching and vesting schedules), health insurance alternatives, and other benefits. Take note of enrollment dates and make decisions based on your family’s needs and financial objectives. Maximize your new employer’s retirement match; it’s basically free money invested in your future.
- Revised budget: A new job usually means changes in income and expenses. Use this opportunity to go over and improve your budget. Take into account any changes to your lifestyle, your new salary, and any potential shifts in the cost of commuting. Prioritize savings and verify your spending is in line with your financial goals.
- Refreshed financial plan: A major life event like a job change, especially at the executive level, requires a reassessment of your entire financial plan. Reevaluate your investment strategy, retirement timeline, estate planning documents (will, trusts, power of attorney), and insurance coverage. Confirm that your plan still matches your current circumstances and your long-term aspirations.
The Bottom Line
At the senior level, navigating a job transition calls for both professional skill and smart financial management. You can pursue a smooth transfer, safeguard your wealth, and confidently march toward your next professional triumph by taking proactive measures to address these crucial financial steps.
The key takeaway?
Don’t let this pivotal moment pass without giving your financial future the strategic attention it deserves.
If you’re looking for a partner for your financial journey, someone who understands how to help people enjoy financial success, you’ve come to the right place.
At Attitude Financial Advisors, we believe your financial success begins with a winning attitude. Your attitude and behavior toward finances has EVERYTHING to do with your prosperity. Our job as your trusted financial advisor is to help you understand your existing behaviors and align them with what you want to accomplish using our unique financial planning process.
Reach out to me for guidance via email at btrugman@attitudefinancial.com or give me a call at (516) 762-7603 to set up a free consultation.
About Bryan
Bryan Trugman is managing partner, co-founder, and a CERTIFIED FINANCIAL PLANNER® practitioner at Attitude Financial Advisors. With more than 17 years of experience, Bryan specializes in addressing the financial needs of new parents as they seek to realign their finances, assisting divorced individuals as they navigate an unforeseen fork in the road, and strategizing with those seeking to accrue a dependable retirement nest egg. Bryan is known for being a good listener and building strong relationships with his clients so he can help them develop a customized financial plan based on what’s important to them. He is passionate about helping his clients experience financial confidence so they can worry less and play more. Bryan has a bachelor’s degree in industrial and systems engineering with a minor in mathematics from State University of New York at Binghamton. He has served on the board of the Financial Planning Association and continues to be actively involved in the national organization. He is also a member of the Plainview-Old Bethpage Chamber of Commerce and has served as its vice president and as a board member. When he’s not working, you can find Bryan on the ballroom dance floor or engaged in a fast-paced game of doubles on the tennis court. To learn more about Bryan, connect with him on LinkedIn. Or, watch his latest webinar on: How Much Is Enough? A Surprisingly Simple Way to Calculate Your Retirement Savings Needs.

