Welcome back to my sabbatical planning guide! If you’re joining me for the first time, I recommend starting with Part 1 where I covered the foundational elements: defining your goals, setting your timeline, calculating your budget, building your financial cushion, and creating your savings strategy.
In this part, I’ll share the practical considerations that often get overlooked in sabbatical planning. These are lessons I learned the hard way through my three sabbaticals (2014, 2019, 2025).
Quick Recap: Where We Left Off
By now, you should have:
- Clear sabbatical goals and a realistic timeline
- A detailed budget with your target savings amount
- A savings strategy and timeline for reaching your goal
Now we’re getting into the part where we turn the plan into reality and navigate some potential practical issues that come with sabbaticals.
Once you’re clear on when and what you’re doing for your sabbatical, we need to address some more practical issues. These might seem mundane, but ignoring them can create serious stress during what should be your rejuvenation time.
Healthcare Coverage
If your health insurance is tied to employment, research alternative options well in advance – ideally at least six months before your sabbatical starts.
Key considerations:
- What are your options if you lose employer-sponsored insurance?
- How much will alternative coverage cost? (Factor this into your budget!)
- If traveling or living abroad, what does your coverage include internationally?
- Do you need separate travel insurance?
- Are there waiting periods for new coverage to take effect?
What this looks like in practice: Switzerland is an anomaly compared to many Western European countries where healthcare is private. It’s usually not tied to your employer, but in my case I worked for the UN where I had special medical insurance under the UN system. I knew I would lose access to the insurance plan, but I also knew you could extend it up to three months after your contract ended during a transition period. I had to arrange this a few months in advance before my last day, so be sure to get on it as early as possible. During those three months, I was able to switch to a private Swiss healthcare program. I know things can be trickier in the US, so make sure you research this way in advance.
Professional Relationships
One of the biggest mistakes people make is disappearing completely during their sabbatical. Your professional network is valuable, and maintaining it doesn’t mean you’re not truly taking a break.
Strategies for staying connected without working:
- Let key contacts know you’re taking a sabbatical and when you’ll be available again
- Attend occasional industry events or conferences that genuinely interest you
- Have informal coffee meetings with former colleagues or mentors (on your terms)
- Stay active on LinkedIn, even if you’re just sharing interesting articles
- Join professional groups or associations related to your field or interests
What this looks like in practice: During my current sabbatical, I’ve been regularly meeting up with former colleagues. It’s not because I’m actively looking for a job or networking strategically – I genuinely enjoy their company. It’s also really nice because we can actually talk about things that matter, like family, friends, and relationships. Previously, we would only talk about work and our projects.
I also started attending networking events, again not necessarily for job opportunities but on topics that genuinely interest me. Just last week I attended an event featuring a wallpaper artist, and I’ve also recently attended an event on biodiversity startups. Turns out that even though I left my job in biodiversity, I’m genuinely still interested in what’s going on!
Skill Maintenance
Depending on your field and how long you’ll be away, consider how you’ll keep relevant skills sharp. This isn’t about working during your sabbatical – it’s about staying engaged with what you love about your field.
Ideas for different goals:
- Take online courses in areas that interest you and that you want to learn (not what you “should” learn)
- Do small volunteer projects that align with your sabbatical goals
- Maintain certifications if they have expiration dates
- Read industry publications or books that genuinely fascinate you
- Experiment with new tools or approaches without deadline pressure
Important caveat: Only do this if it genuinely interests you and supports your sabbatical goals. If your goal is complete recovery from burnout, give yourself permission to step away entirely from anything work-related.
What this looks like in practice: I’m taking a course on how to use Figma. Why? Web design has always been intriguing to me, not necessarily from a web developer or programming sense, but in how information is organized within a webpage and how certain aesthetics and colors attract me to certain websites. I’ve also always been interested in studying color schemes and user experiences. This has absolutely nothing to do with my job, but it’s something I genuinely always wanted to learn.
Step 7: Additional Practical Tips from Experience
These are the insights I wish someone had shared with me before my first sabbatical – the things you don’t realize until you’re actually living it.
Don’t Burn Bridges
If you’re leaving your company, don’t just say “Hasta la vista!” Make sure you have a proper handover process. Say your goodbyes properly and write a meaningful email to colleagues and partners at the end. Do this even if you didn’t have the best experience or relationships at the company. When you send it out, copy your personal email so people can reach you after you’ve left. Add colleagues to your LinkedIn network. If possible, have lunch or coffee with your closest colleagues before leaving and tell them how much you appreciated them. Leave the company in good hands and in a professional way.
Why this matters: I’ve done this after each sabbatical, and I still maintain relationships with many former colleagues. Several have become close friends. Others have recommended me for opportunities years later. You never know when these relationships will matter personally or professionally.
The goodbye email tip: When you send your farewell email, BCC your personal email address so you have everyone’s contact information even after losing access to your work account.
Document Your Sabbatical Experience
You don’t need to make your writing public like I am, but I’ve always found that writing about my sabbatical experiences helps immensely with reflection and serves as inspiration even after returning to work. Even taking daily photos during your sabbatical will serve as keepsakes for this special period in your life.
Ways to document:
- Keep a private journal or diary
- Take daily or weekly photos
- Create a photo book after your sabbatical
- Write reflective pieces about what you’re learning
- Record voice notes about experiences while they’re fresh
- Start a private blog just for yourself
Why it’s valuable:
- Helps process your experiences and emotions
- Provides inspiration when you return to work
- Reminds you why the sabbatical was worth it during tough moments
- Creates a record of your personal growth
- Gives you concrete examples for future job interviews about what you learned
My experience: I’ve kept journals during all my sabbaticals, and I still return to them when I need perspective or inspiration. They remind me of breakthroughs I had, challenges I overcame, and why investing in myself was the right decision.
Transitioning Into Sabbatical Isn't As Easy As You Think
This might be the most important thing I can tell you: the transition into sabbatical life is psychologically challenging in ways you don’t expect.
You might think, “What do you mean? I’m not working anymore, I can do whatever I want, wake up whenever I want – life is going to be amazing!” But you’ll be surprised how deeply conditioned our lives are to work rhythms.
What this actually looks like:
For the first three months, I was completely lost because while I could schedule my day however I wanted, I still had my daily rhythm ingrained as if I was working. My husband would tell me every day, “You’re not working anymore, why do you still go to your home office at 9am sharp to check your email?” This might not be the case if you completely change your setting or travel, but trust me, adjusting to life without work can be mind-boggling at first. Take it slowly.
Common transition challenges:
- Feeling guilty about not being productive in traditional ways
- Struggling to fill time meaningfully without external structure
- Missing the identity and purpose that work provided
- Feeling anxious about not earning money
- Difficulty explaining to others what you do all day
- Unexpected loneliness or isolation
How to navigate the transition:
- Give yourself permission to have an adjustment period (plan for 2-3 months)
- Start with loose structure rather than complete freedom
- Be patient with yourself and the process
- Expect some difficult emotions – they’re normal
- Consider working with a therapist or coach during the transition
- Connect with others who’ve taken sabbaticals
My experience: I was very lucky to be working with a therapist to heal from burnout and also a career coach who helped me navigate the transition. I’m not saying you should get a therapist and coach (they are not cheap, but if you can afford one, I highly recommend them), but do understand that these emotions can arise. One piece of advice that both gave me was to give myself permission to have this adjustment period and acknowledge that I deserved it. I’m also journaling a lot, which has helped me process the emotions.
Connect With Other Like-Minded People
After a while, it feels strange living in a capitalist world where everyone has jobs and is hustling for money while you’re stepping back. It can be hard to relate to other people’s work problems, and vice versa.
Why community matters:
I felt guilt when people asked what I’d been up to and I’d tell them about my latest art project or planning my next trip. Meanwhile, they were stressed about deadlines and difficult bosses. The disconnect was real.
How to find your people:
- Join online communities for people on sabbatical or career breaks
- Look for local meetup groups focused on sabbaticals or life transitions
- Connect with others in Facebook groups or Reddit communities
- Attend events or workshops that align with your sabbatical goals
- Be open about your sabbatical – you’ll be surprised how many people are curious or have done similar things
My situation: I was lucky that my husband was also in career transition, so we had each other. But I also made efforts to connect with others on similar journeys. These relationships provided different perspectives and helped me feel less alone in the experience.
Common Sabbatical Challenges and Solutions
Let me address the specific challenges that nearly everyone faces during a sabbatical. Knowing these ahead of time helps you prepare mentally and practically.
Challenge: Fear of Career Damage
The concern: “Will having a gap on my resume hurt my career? Will employers see me as less committed or capable?”
The reality: After three sabbaticals, I can confidently say that being on sabbatical has never been viewed negatively in my professional development or job searching. Rather, it was always met with curiosity and interest.
How to frame it positively:
- Be confident and clear about why you took the sabbatical
- Highlight specific skills or experiences gained during your time away
- Show how the sabbatical made you a better professional
- Demonstrate continued engagement with your field (if applicable)
- Frame it as intentional professional development, not random time off
Challenge: Sabbatical Guilt or Anxiety
The concern: Feeling guilty about not working, not contributing to society, or “wasting time” when you should be productive.
The reality: This is perhaps the most common challenge, and I experienced it intensely. There were days when I felt like I wasn’t doing enough, wasn’t being productive enough, wasn’t justifying my decision to take time away.
How to reframe it:
My career coach helped me understand that my sabbatical was something I earned and worked hard for. I deserved it. This wasn’t a luxury or indulgence – it was an investment I made in myself through years of saving and planning.
Remember: Investing in your well-being and growth ultimately benefits everyone in your life, including future employers and colleagues. You can’t pour from an empty cup. Taking time to refill your cup makes you better at everything you do afterward.
Practical strategies:
- Work with a therapist or coach who can help you process these feelings
- Journal about your guilt and examine where it comes from
- Remind yourself regularly of your “why” – your sabbatical goals
- Celebrate small accomplishments during your sabbatical
- Practice self-compassion and patience
Challenge: Not Being Good With Money or Planning
The concern: “I’m terrible with finances. I can’t manage budgets. I don’t know how to plan something this complex.”
The solution: You don’t need to navigate the sabbatical path alone, and being honest about your weaknesses is actually a strength.
Resources to consider:
- Career coaches: Can help clarify your goals and guide you through sabbatical planning. I have a career coach who helped me immensely with goal-setting and accountability.
- Financial planners: Can help create a realistic savings plan and manage your finances. Worth the investment if money management isn’t your strength.
- Accountability partners: Friends or family who can help keep you on track with savings goals.
- Apps and tools: Expense tracking apps, budgeting software, and automated savings tools can make financial management much easier.
Remember: Asking for help isn’t a weakness. It’s a smart strategy that increases your chances of sabbatical success.
Is Taking a Sabbatical Right for You?
Before we conclude, let’s have an honest conversation about whether a sabbatical is actually the right choice for your situation. Sabbaticals aren’t for everyone, and they’re not always necessary to achieve your goals.
Consider carefully if:
Career advancement is your immediate priority
Sometimes staying engaged and visible in your field is more effective for reaching your next professional milestone. If you’re up for a promotion, working on a career-defining project, or in a critical growth phase of your career, timing matters. A sabbatical will be there later when the timing is better.
You have severe financial anxiety
Let’s be honest: going on sabbatical means watching your savings decrease month by month, unless you have significant side income covering all expenses. This is mentally challenging even for people who are good with money.
I consider myself financially savvy, but I still get occasional middle-of-the-night anxiety about running out of funds. One night I’ll wake up in a panic thinking, “What if I can’t find work after this? What if my savings run out?”
Ask yourself honestly: Can you handle the psychological stress of seeing your bank account shrink while not earning a regular paycheck? If the answer is no, that doesn’t mean you can never take a sabbatical. It might mean you need to save more, create additional safety nets, or work with a therapist on financial anxiety before taking the leap.
You want to quit without a clear plan
If your primary motivation is “I hate my job and want out,” a sabbatical might not be the solution. This often indicates severe burnout, which requires dedicated treatment and recovery strategies.
I’ve seen people quit impulsively due to burnout, only to spend their entire “sabbatical” period just trying to recover enough to function again, rather than pursuing meaningful goals. They burn through savings while in crisis mode, then face job searching while still exhausted.
Better approach: If you’re experiencing burnout, consider taking medical leave first to address the root issues. Get proper support – therapy, medical treatment, whatever you need. Then, once you’re in a healthier mental state, plan your sabbatical with clear goals and intentions.
Burnout is real and serious. Treat it as a medical condition first, then decide if a sabbatical is still what you want.
You might be ready for a sabbatical if:
- You have clear goals for what you want to achieve
- You’ve saved enough to cover your expenses plus significant buffer
- You can handle the uncertainty and financial stress psychologically
- You have some form of safety net or backup plan
- You’re in a good enough mental state to benefit from the experience
- The timing works with your career trajectory and personal life
- You’re prepared for the challenges and have support systems in place
Conclusion: Making Your Sabbatical Dreams Reality
Planning and executing a sabbatical requires significant preparation, financial discipline, and courage. But for those who are ready, the rewards can be truly life-changing.
Key lessons from my three sabbaticals:
There’s no single “right” way to take a sabbatical. Some people move back in with family, others travel to lower-cost countries, and some maintain their current lifestyle while taking time off locally. The best sabbatical is the one that aligns with your goals, values, and circumstances.
The planning is just as important as the sabbatical itself. The discipline you develop while saving, the clarity you gain while defining your goals, and the self-knowledge you acquire while preparing all contribute to the sabbatical’s success.
The transition is harder than expected, but that’s normal. Give yourself grace during the adjustment period. The psychological challenges don’t mean you made the wrong decision – they’re part of the process.
Community matters. Whether it’s family, friends, online communities, or people you meet during your sabbatical, connection helps you navigate both the challenges and the joys.
Final Thoughts:
Taking a sabbatical is one of the best investments I’ve ever made in myself. Each of my three sabbaticals has shaped who I am, what I value, and how I approach both work and life. The experiences, lessons, and personal growth have been invaluable.
If you’re considering a sabbatical, start with small steps today. Clarify your goals, begin tracking expenses, and start saving consistently. Even if it takes several years to save enough, having a clear plan will keep you motivated and help turn your sabbatical dreams into reality.
Remember: You’re not running away from something. You’re running toward something – toward growth, exploration, recovery, connection, or whatever goals matter most to you. That’s something to be proud of.
I’d love to hear from you: Are you planning your own sabbatical? Currently on one? Considering whether it’s right for you? Share your thoughts, questions, or experiences in the comments below.