Meet John

I am John.

I am a CERTIFIED FINANCIAL PLANNER® professional (since 2019).  John earned his Registered Life Planner® designation in 2024.  

I enjoy working with people who care for others and their community – firefighters, therapists, doctors, nurses, and teachers. As you help others, you also must help yourself. That’s where I come in. I help you put all the financial pieces together into a cohesive strategy that matches you and your desired life.  Just as I encourage my clients to align their finances with their values, I seek to align Trail Financial Planning with my values – supporting families, relationships, community and the natural world.

Meet Liz

I am Liz. I am a CERTIFIED FINANCIAL PLANNER® professional (since 2022).  I enjoy helping women in transition, whether a job transition, divorce, or death in the family.  I love assisting people to navigate the financial world as a single person to bring awareness to their financial lives.  I also love assisting self employed health professionals.

I assist people in getting their financial lives under control and on track so that they can worry less and enjoy their lives more. I will help you figure out what is important, create a plan with you and guide you along the way. I was raised in Bellingham and love living here with my two kids, and our dog. I enjoy being active, getting out and enjoying our geography – skiing and hiking in the mountains and playing in the islands. I wouldn’t chose to live anywhere else!

We formed Trail FP in response to our experiences with the financial industry. Many financial services boil down to “my financial guy” (and they are almost always a guy), and some fancifully-named product like “Aggressive growth in emerging markets ETF.” Imagine if the medical industry worked this way: You have a sneezy, runny nose and persistent hacking cough. You ask your neighbor for advice. He tells you, “I’ve got this health guy, he’s great, he’s even a Huskies fan.” So you go see him. He advises you to buy a bottle of pills advertising, “condensed formula of Pinolenic Acid. It will boost your immune system and lower cholesterol!” He suggests you take one capsule per day, for the next year. The cost is $500 for a month’s supply, but, don’t worry, your insurance will pay! Then you and “the guy” high five over the latest Huskies win. It turns out that you just had a cold, and it just needed to run its course. Also it turns out the doc was receiving $50/month based on his recommendation.

Thankfully, the medical industry does NOT work this way. However, many financial businesses and “guys” still do. Products are difficult to understand. The way people get paid is not clear. Many “advisors” work on commission. When we (John and Liz) shopped around for financial advisors, we found an industry where profits were valued more than people. Even though there are good people working as advisors, the structure often discourages ethical behavior.

We wanted something different. We wanted to put people in front of profits. We come from people professions. John was a high school science teacher. Liz was (and is) a behavior and mental health counselor. We like helping people. We also like thinking and working with financial issues. So, in 2017, Liz and John partnered to start Trail Financial Planning, a fee-only financial planning firm. Fee-only means that we receive compensation only from our clients. We don’t receive any commissions from product recommendations. Our business structure is designed to put the light of day on conflicts of interest, and align your interests with our own. We embrace the fiduciary standard of care for our clients, where we must act in the best interest of our clients over our own interest.

We called our firm “Trail Financial Planning” because we both love trails – the adventure, the unknown, the connection they provide us to nature. A trail also serves as a metaphor. Your financial life is like a journey, like a long backpacking trip. To backpack, you need to have a map, know how to read it, pack right, be fit for the trail, make good decisions along the way, and enjoy the hell out of your surroundings. We help you do the same thing with your finances – set goals, make a plan, save efficiently, monitor your income/spending, and simplify your life so you can enjoy the hell out of it.

Our personal stories

In 2013, I was working in my classroom after school, grading papers, when a well dressed man walked in. He introduced himself and told me that I, as a school teacher, had the opportunity and right to invest in a “403b” retirement savings plan. I told him I was not interested. But he was a good salesman, so he persisted, and asked me why. I told him that I managed my own investments, and tried to turn back to grading my students’ papers. But he kept talking. I finally told him that I was a Registered Investment Advisor. Though this fact finally stopped his original pitch, he just smoothly changed gears. He suggested I should work for his company selling annuities to teachers.

Curious, I asked him for details. He told me that he had been working for the company for five years. By this time, he was making over $150,000/year. He told me how he was doing it, and what the business model was: he sold an annuity plan to teachers in which they agreed to contribute a set amount every month. Each monthly contribution would carry a sales commission – not just once, but every month for as long as the teacher participated. Each commission might not appear to be much (maybe $10 on a $200/month contribution), but if this guy sold a plan to 1,250 teachers, he’d be sitting on $150,000 in commission-based revenue.

I nearly puked on my pupils’ papers. Here I was, busting my butt to help my students think more deeply, critically, and to work hard. And here was this guy – pleasant, well dressed, charismatic, but in my mind, a wolf in sheep’s clothing. I thought about my teaching friends, with huge hearts, trying to make the world better by working with kids, getting attacked by this wolf.

Predatory financial practices like this work because most people know they need to save and invest, but don’t have time to research the details. People have big hearts, and without good information, they trust someone who seems “nice.” I am fortunate that, early in my career, before life became super busy with kids and a house to maintain, I found myself with time and space to really learn about personal finances and investing. I feel equipped to root out the wolves from the sheep.

I was living in South Africa, newly married, with a good job teaching math at an international school. My wife and I were able to save a lot, which was great because I had some big student loan bills to pay off. I became really interested in investing. I read Warren Buffett’s letters about buying and holding great businesses. I read books by The Motley Fool. I read about the idea of “paying yourself first.” I was fascinated by the idea of accumulating ownership stakes in great businesses (stocks). I decided to slow down the pay-off my loans, and instead focus on saving and investing our money.

Fifteen years later we were back in the Pacific Northwest, with two kids, living in wonderful Bellingham. I still woke up early on Saturdays to read through annual reports and check the financials on my investments before kids’ soccer games or a bike ride. I would talk about investing with friends and neighbors. One neighbor told me about his financial investments, which involved a “hot tip” from a co-worker on a commodity index. I suggested he might want to diversify and consider businesses. He said, “Hey Chesbrough, will you just invest my money?”

I looked into becoming an Investment Advisor, but,I was nervous about the industry. I knew that even the best-intentioned people can be corrupted by a bad system. Then I learned about being a “fee-only” Financial Advisor, and becoming a fiduciary (where the advisor must put clients’ financial interest in front of their own, kind of like how, as a teacher, I strive to put my students’ interest first). In 2012, I took the appropriate test and registered with the state, and opened a solo-practice called “John Chesbrough, Investment Advisor.” I soon realized how much more there was to attending to people’s financial world than just investments. In 2015, I started studying the Certified Financial Planning curriculum. I passed the test in November, 2016. In 2017, I partnered with Liz to change my advisory practice into a Financial Planning/Investment Management business, Trail Financial Planning.

I have been a mental health therapist in private practice since 2001. After seeking out financial planning help myself when I was first growing my family, I found planners interested only in investment management, and what money I had to invest. I wanted to do financial counseling and planning, to provide what I felt was being left out in the financial services world: a curiosity about people and how they relate to their finances. I decided to pursue a second career in financial planning.

My career quest took root when, a few years later, I met with a great financial planner who understood my family, and got us on the right track: he helped us set up retirement plans and learn what to save for first. He assisted us with other questions such as: “Should we buy that new car? And should we refinance our mortgage?” His help was invaluable at that time and I slept better at night…I had a plan and I was worrying less about the future! However, when I asked him for help with detailed budgeting strategies, or for help with behavioral changes that might help my husband and me get on the same financial page, he had nothing to offer. We paid him for his financial planning service and for the work he did in setting us in the right direction. It was clear: we paid him a fee and he provided us with some direction. And then… it became really unclear to me how much commission this individual was receiving when he invested our money in his suggested mutual funds.

I started to question how someone could objectively advise me to invest in something for my best interest if he received more commission and incentive for that investment than if he suggested something else. And hey, maybe this is why he was not interested in my budgeting questions; there wasn’t a lot of money to be made by diving into those questions. He couldn’t earn a commission for that work! And then my trust eroded. I could not get my mind around fully trusting this advisor’s investment recommendations when he was directly profiting from those suggestions. As a therapist, I avoid dual relationships (like being a salesperson and an advisor), as they introduce inherent conflicts of interest. However, it is a surprisingly common practice in the financial services world to receive commission on one’s recommendations.

It was then that I decided I wanted to provide the community something I was finding difficult to find myself, a planner who is truly interested in the complete financial picture: values and behaviors as well as finances and investing. I wanted to provide a fiduciary, fee-only practice, separating my compensation from the products and services I recommended. Thereby, I could provide advice in my clients’ best interest, and not be conflicted with my own. And that is what I have done.

I provide clear, comprehensive financial planning and advice to people who do not know where to begin organizing their financial lives, how to save or start building wealth, or how to keep it going once they have a clearer picture of their financial path. I help my clients explore who they are, what their values are, and whether or not their money behaviors are consistent with their values.  We work together to link values and behaviors to reach future goals.  I provide hope to people that they can become financially cohesive regardless of their past behavior and that they can have the opportunity to build wealth and feel confident in their financial situations and life choices.

I work primarily with new families and those wanting to dive a bit deeper into their financial psychology. Although I will not be your therapist, I cannot help but bring my years of listening, assessment, and problem solving experience as a therapist to your financial plan.  I get to know you, what your finances are, and how you relate to your finances so that you can feel more comfortable about where you are headed on your financial path.