A Life Too Good: The Struggle is Real for Will Kaplan, Other Financial Planners to Grasp Success

3 min read
February 22, 2017


After helping to get his family out the door, Will Kaplan starts each day with “coffee, calendar and email,” in that order. It’s no surprise that each day is prioritized like his life – family first.  The elusive work-life balance is what draws many to the field of financial planning in the first place, and motivates many like Kaplan to start their own firms.

Like others who have caught their stride in the industry, the life he created for himself sometimes seems too good to be true for Kaplan.

Even when “doing all of the jobs, all of the time” as an entrepreneur, Kaplan struggles to grasp that the payoff is really possible and well-deserved. “Starting a business…is a hard job,” he said, “It takes determination and a willingness to confront the fear of failure. I constantly struggle with imposter syndrome and a fear of failure.”

Kaplan is, in fact, the real deal. His accomplishments in business recently earned him the distinction of Member of the Month from XY Planning Network, the leading organization of fee-only financial planners who serve Generation X and Generation Y clients. The peer-nominated honor means Kaplan is not just legit, but also a recognized leader within the network.

“It’s more than the fact that Will is very knowledgeable,” said Maddy Roche, a director with XYPN. “He was nominated by other financial planners because they identified Will as someone who consistently goes above and beyond to connect with and help his peers.”

Kaplan is humble about his esteem within the network. “XYPN has provided something that is hard to find: the shared experience of others,” he said. “Being able to see how other people tackle the same problems means I don’t have to make all the mistakes myself, which is the definition of wisdom.”

Truth be told, Kaplan has accumulated a wealth of wisdom after a handful of years in the business. His Portland, Oregon-based firm, Halcyon Financial Planning, proudly serves the next generation of up-and-coming professionals, as well as those approaching retirement. He’s inspired by helping his clients affect change in their lives and achieve their own goals. Working with Gen X and Gen Y clients is ideal for Kaplan because he believes the best financial move is getting started early. “Time is everyone’s most valuable resource,” he said.

In addition to time, solid financial planning is key to setting oneself up for success. “Good financial advice…is more than your accounts, your tax returns, and your monthly budget,” says Kaplan. “Financial planning is the process of transforming your resources, regardless of what they are, into your accomplishments.”

Growing up in Houston, Texas, he took an interest in finance as a high school student. His father would cap off each week watching Wall Street Week during their family dinner on Friday nights.  Kaplan paid attention too and eventually picked up some early shares of Intel stock for himself.  “It went up,” he said, “I thought I was a genius.”

Quiet as kept, Will’s stroke of genius proved to be a case of perfect timing, as he happened to jump into the market at a time when any tech stock would’ve shown the appreciation of his Intel shares. Upon realizing that financial acumen was about much more than getting lucky, Will sought to learn the nuances of personal finance that could only come through the acquisition of hours (10,000 to be exact) of doing the work of a financial advisor.

He made his way to Chicago via college in Ohio and started his career in finance with a very small fee-only firm before ultimately settling his family in Portland. It was the time spent at this firm where he really began to learn the business.

Nowadays, Will is a fixture in the XYPN community sharing the knowledge he’s gained over the years with new and experienced advisors, alike. Not one to take credit, Kaplan attributes the community aspect woven into the culture of XYPN with why he remains such an active presence among his peers.

“There’s no doubt I’m a better advisor because of the relationships that I’ve built through XYPN.” He continues, “Without XYPN, new advisors would have very little direction in starting their firms. So, if sharing my personal experience helps fellow advisors avoid mistakes and speed up the learning curve, I consider it the least I could do to show appreciation for those that offered me a helping hand at the beginning of my career.”