Taking a Career Break with Confidence: How to Prepare for What’s Next

As the holidays approach, life naturally slows down, offering a rare moment for reflection. Maybe you’ve been feeling a pull to step back, reassess, and reset. For many professionals, this season becomes the perfect time to ask:

• Am I ready for a change?
  
• Am I burned out and craving a break before my next adventure?
  
• Am I dealing with a workplace that no longer feels right for me?
  

If any of that sounds familiar, you’re not alone. However, before you rush to hand in your resignation letter, it’s worth taking a few thoughtful steps to ensure your transition feels empowering, not stressful.

Here’s a practical and reassuring roadmap to prepare for your next chapter.

1. Reflect on Your “Why”

Before making any big move, take a moment to dig into what’s really driving you. Are you looking for peace after burnout? Searching for a new challenge? Wanting to reclaim balance and joy?

Understanding your “why” will empower you to make intentional decisions about how long to take off, what you want to explore next, and how to explain your journey to family, peers, or future employers.

2. Build a Financial Runway

Freedom feels best when a solid foundation supports it.

Map out your expenses for the next 12–18 months and plan for a period without regular income. Include recurring bills, discretionary spending, and unexpected costs.

If you work with a financial advisor, this is a great time to discuss tax projections, cash flow, and withdrawal strategies. (Roth conversions can be powerful, but covering your monthly bills comfortably comes first.)

A clear financial plan gives you peace of mind but also the freedom to focus on renewal, rather than worry.

3. Plan for Health Insurance

Health coverage can be one of the trickiest parts of a career break, so tackle this before you resign.

• COBRA is convenient but often pricey - $400–$700/month for individuals and $2,000–$3,000+ for families.
  
• ACA Marketplace plans are worth exploring; subsidy eligibility depends on your expected adjusted gross income.
• Concierge Doctor memberships can be coordinated with plans to reduce premiums while protecting against the unexpected.
• Faith-Based “Medishare” plans are an opportunity for some as well

Make a list of your doctors and prescriptions, then talk with a health insurance advisor to ensure you’re covered without overpaying.

4. Protect Your Benefits & Agreements

Before you part ways, check in with HR about what benefits you can keep. Many professionals overlook things like:

• Group life or disability insurance portability
  
• Vesting schedules can help you make informed decisions about the timing of your career break.
  
• Stock options or deferred compensation
  
• Non-compete or non-solicit clauses
  

Get copies of all relevant agreements now—it’s much easier to clarify terms before you leave than after, ensuring you are well-prepared and secure.

5. Understand Resignation Benefits

A well-planned exit can sometimes unlock unexpected support. If your departure stems from a toxic or hostile environment, you may be eligible for severance pay, continuation of health benefits, or even employer-subsidized COBRA premiums. These benefits can significantly ease your transition and provide a safety net as you embark on your career break.

An employment advisor can help you understand your rights and options. Many offer free initial consultations, and this guidance can make a big difference in how you frame your exit.

6. Finalize and Execute Your Exit Plan

Once you’re ready, draft your resignation thoughtfully. Prepare a professional notice, outline your transition plan, and make sure your projects can be handed off smoothly.

Two weeks’ notice is standard, but offering more—when possible—shows integrity and ensures you leave on excellent terms. A graceful exit preserves relationships and strengthens your professional reputation.

7. Reconnect and Reassess Regularly

Your career break isn’t just time off—it’s time for something. Use it intentionally. Check in with yourself every few months:

• Are you resting and recharging?
  
• Are you discovering what excites you next?
  
• Are you staying connected to your network and mentors?
  

This period can be one of the most transformative times in your professional life—if you approach it with curiosity and care.

The Bottom Line

Taking a career break can feel daunting, but with the proper preparation, it becomes an act of courage and clarity—not chaos.

You’ve worked hard to get where you are. Now, it’s about giving yourself permission to pause, reflect, and rebuild the next chapter on your own terms.

If this resonates with you, consider what would make this break meaningful. And if you’d like a personalized assessment of your financial readiness or guidance on how to structure your exit, contact your Farther advisor or reach out for a consultation.