We’re Taylor Anderson, CFP® & Kailie Abascal, CFP®, co-founders of Middleton & Company. We are moms, hard workers, dreamers, and financial planners.
We believe in non-traditional career paths and some spontaneity, but also in financial security. We specialize in helping mid-career professionals take sabbaticals or career breaks… the smart way! We combine financial expertise with peace of mind to help you make it happen.
Today, we’re diving into a big and exciting topic: the family sabbatical.
Both of us have taken sabbaticals before having kids (solo in Mexico for Kailie, Taylor with her husband in Kyrgyzstan). Those experiences led to career changes, lifestyle shifts, and lifelong memories. Now, as parents of two, we’ve traveled with our families of four and are planning another sabbatical with our kids, while helping clients do the same.
We want to show you what it can look like, based on real client experiences, to inspire you and remind you:
✨ It is possible to hit pause while your kids are young, explore the world, immerse them in new cultures, and create lifelong memories…while investing in your future and returning rejuvenated, with clarity and purpose for your career.
Today, we’re sharing Katie & James’ story.
(Note: This is a hypothetical scenario, inspired by multiple client experiences to honor privacy.)
If your situation isn’t exactly the same, don’t worry! Sabbatical planning is not a one-size-fits-all solution. It’s deeply personal, designed around your family’s goals, needs, and finances to make the most of your unique situation.
Meet Katie & James
Katie (38) is a recruiter.
James (40) is a software engineer.
They live in Seattle with their two kids (ages 5 and 7).
⛰️Both are outdoor enthusiasts who love hiking, camping, and exploring national parks but rarely have time for extended trips. They’re driven and passionate about their careers but crave a slower pace for a while, wanting to introduce their kids to different cultures and spend quality time together away from the daily grind.
Their Goals:
✅ Take a 6-month family sabbatical to travel and be together
✅ Experience slow travel in Europe and South America
✅ Ensure financial security while away and a smooth return to work
✅ Continue saving for retirement and college funds
Their Fears & Challenges
When they started dreaming about a sabbatical, they worried:
⚠️ “Will we find jobs when we return?” They were nervous about what it would be like to re-enter the job market.
⚠️ “Can we really afford this?” They feared they might be jeopardizing long-term financial stability.
⚠️ “What about our retirement?” They didn’t want to delay their retirement plans.
⚠️ “Can someone just plan this for us?” They already had a busy life and a never-ending to-do list. They kept postponing researching logistics for such a big adventure and they just wished it could all just magically be done.
⚠️ “Will it be too hard for the kids?” They felt like taking them out of school was a big step.
⚠️ “What don’t we know?” They felt stuck in the fear of the unknown. They worried they were missing something.
They had dreamed about taking a sabbatical for years, but it remained just that…a dream! Until they saw a friend return from their own career break, with so many pictures and memories to share and a fresh perspective they had gained. They decided it was time to explore if it could be possible for their family too, otherwise they would end up regretting not doing it!
And that’s where we came in. To help explore what was possible!
If you share similar doubts, check out this blog: Sabbatical Planning: Your 5 Essential Questions Answered By Financial Planners
Katie & James’ Financial Situation Before the Sabbatical
Annual Household Income: $520,000
Assets:
💰 $775,000 in retirement accounts (401(k)s & IRAs)
💰 $1,500,000 in liquid savings & investments
💰 $500,000 in RSUs
🏡 Home in Seattle with $650,000 in equity
Our Approach: Turning Dreams Into Reality
We’re so passionate about helping families like Katie and James take their dream sabbatical because we’ve seen firsthand the incredible difference that support and financial planning can make. With the right guidance, structure, and accountability, “someday” turns into a confident, well-supported plan and lifetime memories!
Our 6-Phase Sabbatical Planning Program:
We’ve developed a 6-phase process to guide families through planning a sabbatical with clarity and confidence. In Katie and James’s case, we worked through all six phases together, but it always depends on your unique situation. Every sabbatical journey is different, and we tailor the process to fit your needs, goals, and life stage.
1️⃣ Sabbatical Readiness – Full financial assessment to evaluate what’s possible
2️⃣ Ideas & Limits – Space to talk, dream, and align plans with your situation
3️⃣ Research & Development – Travel planning guidance and resources
4️⃣ Execution – Personalized investment management and tax strategies
5️⃣ Homeward Bound – Planning your smooth return to life and work
6️⃣ Ongoing Planning – Year-round advice before, during, and after your sabbatical
Our process is structured yet conversational, making it an enjoyable step-by-step experience incorporating:
✅ Financial planning ✅ Travel and lifestyle design ✅ Guided self-reflection
Katie & James’ Sabbatical in Action
Katie & James took a 6-month sabbatical with their kids, turning their dream into a memorable lifetime experience.
🌍 Where they went: Portugal, Spain, and Costa Rica, living slowly and intentionally in each place
🏄 What they did: Visited local markets, hiked coastal trails, surfed, and watched their kids learn new languages and make friends
👨👩👧👦 Who they met: Other families on sabbatical, building lifelong connections
🔄 What they discovered: A new sense of freedom, having more flexibility into their days, even post-sabbatical
💳 How it worked: They had money when they needed it, while we managed retirement contributions, rebalanced investments, and leveraged tax strategies in their lower-income year. When it was time to return, they had a financial buffer planned in advance, giving them space to ease back into work and daily life without pressure.
💼 Their careers: James returned to a flexible new role, and Katie pursued a creative project she had been dreaming of
🎨 Their lifestyle: They built rituals like family cooking, journaling, and evening walks
📅 Their future: Before unpacking, they blocked off a placeholder for their next sabbatical in two years
Why Do Some Families Take Sabbaticals While Others Stop Themselves?
✨ Commitment ✨
Life will always have responsibilities, but when you commit to your sabbatical, the magic happens, and your dream begins to take shape.
We’re here to guide you every step of the way:
✅ Cheering you on
✅ Keeping you accountable
✅ Bringing financial and sabbatical expertise for a smooth, confident journey
✅ Connecting you with a like-minded community
You might not realize it, but many families are already taking sabbaticals, and each one looks different, adapted to their unique needs and situation.
You don’t have to figure this out alone.
Sometimes, it just takes one conversation to clear the doubts: Can I really do this?
Don’t count yourself out before exploring what’s possible. We offer a free 30-minute call to chat about your options.
✨ Let’s talk and see what a sabbatical could look like for you.
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Kailie Abascal
Kailie is a Certified Financial Planner (CFP®) with a passion for helping clients navigate their financial strategies with creativity and confidence. Having lived in Cuba and Mexico, she brings a global perspective to her work, combining her diverse experiences with a deep understanding of financial goals. Kailie is dedicated to helping clients plan for sabbaticals and career breaks, ensuring these life changes are enriching without compromising long-term financial security.