John Chesbrough, CFP® Trail Financial Planning LLC

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About John Chesbrough, CFP®

My path to financial planning has been sinuous, varied, adventuresome. The way I work with people and their financial lives can be understood through my journey Trailo today. Thus, I will start my story at the beginning.

I grew up in Corvallis, Oregon – elementary school, kid soccer, high school, first kiss, Bachelor of Science in Civil Engineering – the whole bit. I was fortunate to have two loving parents. My mom was the financial stability in the family – she worked at a steady job with the university, helping scientists with their writing. She is now known as the “Grammar Grandma” in our family. She taught me to love words, but also gave me a chronic case of the worries. My dad was more of a maverick, boldly lunging from one line business venture to another. He valued people and life experiences over career. He taught me to love the world and its inhabitants, but also stuck me with a “grass is greener” mentality.

After finishing university in 1994, I longed to expand my world. I bounced around Oregon, then moved to Montana to work as a wilderness therapist. I spent week-long shifts as a guide/therapist with groups of juvenile delinquents who were working through the consequences of their actions. We explored the wilds of nature and the wilds of the human spirit. There, I met a girl who captured my heart – Amy. Amy was a free spirit, but also highly practical. She was, and is, very careful with her money; she embraces frugality. She continues to teach me to love a life we are living rather than long for a life we are not.

I enjoyed working with teens but yearned for more academic work, so I went back to school to become a high school teacher. I earned a Masters of Science in Physics and a teaching certificate. After graduation, but before starting a family, Amy and I wanted to explore. We found jobs working as educators at an international school in South Africa. We got married, and four days later moved to Johannesburg. We lived there for two years, where we were blessed to forge deep friendships with people around the world. We also were earning our first real paychecks and found ourselves with extra money. I realized that despite earning heavily math-based degrees, I did not understand the math of money whatsoever. I needed a new education. So I began a path of self-study, reading every book and website I could about investing and personal finance.

Our daughter, Mia, was born in South Africa, and we wanted to move back to the US, to be closer to family. We decided on Bellingham, WA. It is a quiet, livable city, with easy access to the trails of North Cascades and Chuckanut’s. Perfect. I found a job teaching high school science and math, but in my off hours, I continued to learn and experiment with financial matters. Our son, Porter, was born two years later. With two young kids, money grew tight. But, we managed to buy a house and still save some of our earnings for the future.

I started trying to get friends to participate more directly in their own financial lives. We started an investing club called “Stocks and Suds.” I’d bring spreadsheets, they would bring beer. Mostly, we just enjoyed the suds. A few friends started asking if I’d manage their money for them. So, in 2012 I started a solo investment advisory business. I focused on helping people set up little “hobby” investment accounts, like Roth IRAs, in addition to their work-based retirement plans. Within a few years though, people started asking me to help them with more of their financial lives. I became aware that there was much more to finance than just investments.

One of my wife’s therapist colleagues, Liz, started talking to me about my business. Liz was also interested in helping people with their financial lives. We discussed going into business together, with a broader focus on financial planning rather than just investments. I could see a transition coming up, so I took a half-year off from teaching. My family spent four months traveling through Southeast Asia. Our trip was a microcosm for sound financial planning – set a goal, create a budget, save for it (we’d been saving for several years), then adventure! We learned to blog together, to rejoice together, to gag together, and to exist together in tight quarters. Our trip was called “Cheeseburgers in Asia.” Our blog can still be found with a simple Google search. When I returned from our travels, Liz and I began building the business in earnest. We launched “Trail Financial Planning” in June 2017.

Our business is doing well. I can feel the windswept adventure of starting a business from scratch. But my knees are scratched and banged up from the missteps I’ve made. My dad would be proud of the journey. I get to work with people, to help them alleviate fears and worries. My mom approves. I help people care for their pennies. My wife is satisfied. Most of all, I am content. I get to work with people in an ongoing act of stewardship – while we care for their finances, we are really caring for their futures, their loved ones, their dreams, and their missions.

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Disclosure

The annual XYPN membership fee paid by this firm is in consideration of a variety of services and benefits provided by XYPN to its advisor members - including the ability to be listed in this Directory. For a complete description of current XYPN member benefits, please refer to the Membership Benefits section of this website. For current membership pricing, please refer to the Pricing section.

XYPN, due to the compensation it receives from advisors in the form of the annual membership fee, has an incentive to list only these such advisors in the Directory. This creates a material conflict of interest.

Ideal Clients

  • Cash Flow/Budgeting
  • College Planning
  • Gen X
  • Investment Planning & Management

Ways Advisor Charges

  • Hourly
  • Assets Under Management

Fee Options

  • Hourly Fee: $150+/hr
  • AUM: 1.0%

SEC Records

Disclosure

The annual XYPN membership fee paid by this firm is in consideration of a variety of services and benefits provided by XYPN to its advisor members - including the ability to be listed in this Directory. For a complete description of current XYPN member benefits, please refer to the Membership Benefits section of this website. For current membership pricing, please refer to the Pricing section.

XYPN, due to the compensation it receives from advisors in the form of the annual membership fee, has an incentive to list only these such advisors in the Directory. This creates a material conflict of interest.

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