When a Career Pivot Feels Like Starting Over
“You may encounter many defeats, but you must not be defeated.”
Dee was in her late 50's and, after decades as a teacher, had recently launched a consulting company.
On the one hand, retirement would have been nice - teaching was increasingly challenging in the years following COVID, and most days she felt burned out. But there was also part of her that didn't feel quite done.
Still, switching careers wasn’t proving to be any less taxing, and she was beginning to wonder if it was worth all the work at this point in her life. Her previous salary and retirement benefits were at least stable, and now she felt pulled in a million different directions.
Dee found herself wondering:
Did I make the right decision?
Am I doing more harm than good for my (eventual) retirement?
How do I make sense of my current financial situation?
For women in their 50s and beyond, a career pivot—or re-entering the workforce after a break—can feel both exciting and intimidating. If you’ve been in Dee’s shoes, you know it’s possible to chart a new course, but it takes intention and planning to make it work.
Step One: Reassess Your Financial Priorities
A career change often means adjustments to your income, benefits, and financial goals. Start by getting clear on what matters most:
Rebuild Your Emergency Fund. If your income has changed or you’re in a probationary period, aim to have 3–6 months of essential expenses set aside.
📖 Learn more about the importance of an emergency fund.Check Your Benefits. Review your new employer’s benefits package, including retirement plans, health insurance, and perks like professional development funds. Contribute enough to maximize any employer match on retirement accounts—it’s essentially free money. And if you're self-employed like Dee, reach out to a trusted financial professional who can guide you on how to set up retirement contributions that make the most sense to you.
📖 Explore tips for maximizing workplace benefits.Adjust Your Budget. Revisit your monthly spending. If your new salary is lower or takes time to stabilize, consider scaling back temporarily. Small changes, like reducing subscriptions or dining out less, can free up funds for your goals.
Step Two: Rethink Your Retirement Strategy
A career pivot doesn’t mean derailing your retirement plans—it means revising them:
Roll Over Old Accounts. Consolidate any 401(k)s or retirement accounts from previous employers into an IRA or your new employer’s plan. This simplifies tracking and managing your investments.
📖 Learn how to roll over your 401(k).Catch Up on Contributions. If you’re 50 or older, take advantage of catch-up contributions for 401(k)s or IRAs. These extra savings can help you close the gap if your pivot caused a temporary dip in retirement contributions.
📖 Read about catch-up contributions and their limits.
Explore New Options. Some career pivots open doors for side income or freelance work. Consider directing part of this income into your retirement savings to boost your future security.
This process can feel daunting, but putting it all on paper is empowering. It helps you see where you stand and identify what needs attention.
Step Three: Give Yourself Permission to Learn
Starting over can feel overwhelming, but it’s an opportunity to grow:
Focus on Financial Education. If your new career involves unfamiliar financial concepts (e.g., stock options, fluctuating income, or new tax brackets), take time to learn. Podcasts, books, or a consultation with a financial planner can make these topics less intimidating.
Lean Into Your Network. Connect with peers and mentors in your new industry. They can offer strategies, share opportunities, and help you thrive.
Celebrate Progress. Recognize even small wins—like hitting a savings milestone or mastering a new skill. Progress builds momentum and confidence.
Dee’s Step Forward
Together, Dee and I embraced the challenge step by step:
Created a SEP IRA and set up automatic contributions to her new retirement plan.
Opened a Health Savings Account (HSA) to prepare for future medical expenses.
Organized her cash flow and aligned her new salary with her long-term goals, to ensure she was still on track to retire at 65.
Most importantly, Dee gave herself grace. Instead of focusing on what she left behind and the chaos of the transition, she’s now embracing the possibilities ahead: a career that energizes her and a financial plan that supports her next chapter.
If You’re Starting Over, You’re Not Starting from Scratch
Pivoting careers in your 50s might feel risky, but it’s also an opportunity to redefine your life on your own terms.
💡 Your first step forward? Reassess where you are, where you want to go, and what’s standing in the way. Even if it feels overwhelming, clarity comes with action.
Let’s Build Your New Roadmap
If you’re starting over, re-entering the workforce, or changing careers, I’m here to help align your finances with your goals.
Click here to schedule a free consultation.
Or send me your biggest question about managing a career pivot. Together, we’ll create a plan that fits your new path.
You’re More Resilient Than You Think
Starting fresh takes courage and grit—it’s proof of your ability to adapt and grow.
And I know you can do it.
With Warmth & Strength,
~Jess
P.S. Know someone considering a career pivot? Share this newsletter with them—they might just need this encouragement today. 🙏
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