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Finance Expertise & Travel Passion Meet

Middleton & Company is not your typical financial planning firm. 

We of course know our numbers, and we love them! But there is something else we are super passionate about…traveling! 

Traveling has always been part of our life… and we’ve made it a point to make it part of our career, too! 

We were good at checking all the boxes to be considered “successful” with good GPAs in college, working at big companies and climbing up the ladder. As passionate for our work as we are, we quickly started losing that spark, creativity, and motivation for day to day work. 

We knew we needed to make space for extended breaks in our life… and we want to help you do that, as well! We’ve realized we are far from the only ones with both the career and travel itch!  We love our career, we are good at our job, and we have big dreams and goals for it. And we’re not afraid of it. But we also know there is a lot more to life than our jobs. We know we need to take extended breaks to go explore the world and keep getting to know ourselves better, too! 

We make your sabbatical dream a reality! 

sabbatical travel break

We’re not talking about just any kind of traveling. Of course, going on a weekend trip or week-long vacation is fun and feels reeeeeeally good. We’re talking about taking a LONG break – a year or two sabbatical break! 

Here’s the catch. Going on long breaks requires a certain organization and financial security and planning! 

So we made sabbatical planning part of our mission! By mixing what we are good at: financial planning with what we are passionate about: traveling and exploring the world, we’ve created something quite special and exciting! 


We are on a mission to make sabbatical breaks not only possible
but also an important, intentional, and rich part of your career through smart financial planning! 

Who are we?

George Middleton

Our firm started with one person: George Middleton.

While working as a CFO of another company, he started out with an interest in managing his own investment portfolio, which turned into sitting for (and passing!) three different certification exams to gain his Chartered Financial Analyst (CFA®) designation so that he could do the same for others.

He loved (and still does) nerding out on the actual portfolio construction and investment selection, and narrowed his scope of work to mostly that, particularly focused on retirement accounts.

He brings 30 years of expertise to the table! 

Taylor and Kailie, daughters of George, joined him in 2017 and added on the financial planning arm of the firm. This launched our family business known today as Middleton & Company. Although portfolio construction is still one of our areas of expertise, we consider it to be a tool to implement the plans, rather than being the sole service we offer.

Taylor Anderson began her career in consulting and project management roles at large companies, so she knows what it’s like to make decisions on benefits, to advocate for herself in annual reviews, and to navigate corporate work environments.
Her passion for personal financial planning started when she and her husband decided to take a break from their traditional career paths in Seattle to join the Peace Corps. She served for 2 years in Kyrgyzstan before joining Middleton & Company.
She loves working with clients who are ambitious in both their careers and their hobbies, and is most excited when she gets to hear about her clients’ travel plans. Her favorite challenge is to help her clients build flexibility into their financial plans so they’re able to enjoy the twists and turns of life as they come.

You can count on her to bring creativity to the world of finance. She love making financial concepts visual and understandable for her clients. 

Taylor Anderson Middleton
Kailie Abascal

After college, Kailie Abascal did her fair share of international travels.

She moved to Oaxaca, Mexico for 3 years, teaching English at Berlitz. She then married her Cuban husband, who she met while studying abroad in Cuba during college.

They moved back to the US together so Kailie could start graduate school at NYU. After her masters’ degree in Latin American Studies, she worked at the Council of the Americas in New York… and hated it! From living in the city to feeling underpaid and underappreciated, she knew this wasn’t her forever job.

She now loves helping clients think creatively about their financial plans. 

Finance + Travel

Yes, traveling and finances have always been a big part of our family.

We got exposed to the finance world through our dad and that’s been a really important factor for us. We grew up in a space where we felt comfortable talking about and handling money. We had Roth IRA accounts as soon as we got our first jobs. 

And we caught the travel bug early on, too! From our first international family trip (other than Canada) to London during middle school, to hosting multiple international exchange students, to Rotary Youth Exchanges in high school, we were exposed often to various cultures and languages.

It only makes sense that we are still making space for travel in our lives with the support of financial planning… and we help you do that, too!


We are proud to be a family business with 30 years of investment management experience
and the freshness of next-generation financial planning.

These experiences made us who we are today and put us in a position to help you get your finance and travel desires met, too! 

Finances don’t have to be hard or annoying. On the contrary, we want to help you better understand your finances to help you achieve your biggest and wildest dreams, such as quitting your current job to live your own eat-pray-love story. 

We’re here to:

  • Provide financial advice to help you manage your money so it works towards your dreams.
  • Help you define & achieve the clear goals you are working towards instead of continuing the status quo.
  • Help you find meaning in your life’s work, and validate that extended breaks are an intentional part of a career.
  • Help you find adventure and renewed energy in your life through sabbaticals.

✈ If you’ve always thought there must be more, but felt like the outsider with these crazy dreams , well, let us tell you – You’re not the only one! And you can have it all!

traveling sabbatical year

Let’s step away from the beaten path, shall we? We will help you think creatively to pave your own journey, wherever that leads you!

Join our community of aligned and joyful professionals who take breaks! Schedule a call now and share those dreams of yours you’ve been hiding away! 

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This blog post is provided for educational, general information, and illustration purposes only. Opinions expressed herein are solely those of Middleton & Company, unless otherwise specifically cited. Material presented is believed to be from reliable sources and no representations are made by our firm as to another parties’ informational accuracy or completeness.
Nothing contained in the material constitutes financial or tax advice, a recommendation for purchase or sale of any security, or investment advisory services. We encourage you to consult a financial planner, accountant, and/or legal counsel for advice specific to your situation. Reproduction of this material is prohibited without written permission from Middleton & Company, and all rights are reserved.