3 Steps to a Successful Career Transition

Amy Shepard of Sensible Money discuss the three steps to a successful career transition.
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By Amy Shepard, CFP

A few years ago, I realized that the job I had loved for many years was no longer as fulfilling. Something was missing and I knew it was time for a change. After looking back on my roughly nine-month journey to find something new, I discovered that my transition could be outlined in three distinct steps.

A Quick Background

In 2013, I began a career in the field of personal finance. It was sort of by accident. After seven years of changing my mind in terms of “what I wanted to be when I grew up” (and many different college majors as a result), I finally earned my Bachelor’s degree in Accounting.

As I ventured out to see what the entry-level accounting world had to offer, I wasn’t finding any positions that really spoke to me. Amidst my search, I found a posting for a company called LearnVest - a fintech startup with a powerful mission, passionate employees, and a ton of opportunity to learn and grow. I took a chance that ended up changing my life forever - both professionally in terms of my career path but also personally in more ways than I can count.

The long story short is that I loved what I did every day. I got to do meaningful work by helping people with their money while also leading teams to do the same. I was challenged to learn new things. I was given opportunities to grow. I met so many smart and wonderful people.

But in mid-2018, things changed. As a result of an acquisition, LearnVest was shut down and I was no longer working with clients. While I was still doing work that I enjoyed, particularly in the leadership realm, the lack of direct client work was really something I missed. So, I set out to find something new.

Step 1 - The Lottery Question

As I began my search, the first thing I asked myself was:

If I won the lottery and money was no object, what would I want to do for "work"?

For me, the answer was easy - I'd want to help people with their money. Maybe from a mountain cabin, or a beach, or wherever I wanted, but I would want to do that without a doubt. If I didn’t have to worry about income, thanks to my lottery winnings, I’d start my own financial planning business. I’d get to work with clients but also embrace ongoing challenges as a business owner. That would be my American Dream.

Now that I had the dream envisioned, how would I implement it? Having my own financial planning business would likely mean a few years (at least!) of little to no income as I got things up and running. With where I was at in my life (having two young kids and my husband staying home with them), this wasn’t a risk I was ready to take on. Additionally, things like compliance, marketing, technology, and many more aspects of building my own business would have to be addressed. All of these are things that I wanted to learn more about.

So how could I do both - work with clients and learn about building and running a business?

Step 2 - Two Steps Forward

Going through an acquisition and subsequent integration at my last firm undoubtedly meant change. Part of working through change meant we occasionally had executive leaders visiting our department to talk about how things were going. During one of those visits, someone asked a question about career growth and the response from my executive leader was something that really stuck with me. He said something along the lines of:

Don’t think about where you want to go next. Instead, think about where you want to be two steps from now. If you can figure that out, then you’ll know what the next step should be to help you get there.”

After thinking long and hard, I decided that in two steps I would want to be in a position where I could work with clients but also manage a business via a partnership or succession planning path. That would give me all of the things I was looking for in terms of my American Dream, but it would allow me to do it in a way that wasn’t as risky as starting my own business.

Now that I knew where I wanted to be in two steps, I could focus on my next step - finding a firm with the long-term potential I was looking for.

Step 3 - Values

So now I know what my American Dream is. I also know what tradeoffs I’m willing to make and the broad two-step path to getting there. It’s time to start looking!

I initially started my search by networking and talking to as many people as possible who were in the financial services industry. I am grateful that so many wonderful people were willing to help! The job leads were plentiful and I met and talked to anyone who was willing to spend some time with me.

Because I had unintentionally gone through the first two steps, I knew what I was looking for: I wanted to find an opportunity to work with clients again but also an opportunity that provided the ability to grow into a significant leadership role down the line. Having this all mapped out made the interviewing process a lot easier. I was honest about what I wanted and what I didn’t want when talking to potential employers. I didn’t waste my time (or anyone else's time) by proceeding through the interview process if the firm didn’t seem like the right long-term fit.

I soon realized that there were a lot of really great options out there! I started analyzing each opportunity by making a mental list of pros and cons. With so much information floating around in my head, it began to feel overwhelming! How could I help myself to methodically sort through all the options and truly find the right fit?

Well, I followed some of my own advice. Several years ago, while working on coursework for the Behavioral Financial Advisor™ (BFA™) designation, I learned about values-based planning. I had incorporated that type of planning in the work I did with clients - I would encourage my clients to identify their individual values so they could use them as a guiding light when making financial (and non-financial) decisions. I used this process in my own financial life, too. I decided to apply the same approach to my job search.

The values I came up with for my newly defined path were:

  • Passion for holistic financial planning
  • Lots of learning potential
  • Ability to build lasting relationships with clients (rather than a call center approach or one-time product sales)
  • Long-term growth potential (partnership/succession planning)
  • Flexible hours (not simply punching a clock)
  • Location

Writing down these values and comparing them to all of the options I was considering was a tremendous help. It was especially beneficial when I was faced with two really great offers. Before comparing each opportunity to my values, I was agonizing over the decision - it was incredibly stressful! I was so lucky to have two amazing offers but I was also very stressed because I didn’t want to make the wrong decision. Ultimately, I don’t think either one would have been the “wrong” decision, but I still needed an informed way to decide. My values were a key component to helping me arrive at a decision, especially since both firms offered many of the things I was looking for. As a working mom with a young family, the deciding factors were flexible hours and location.


When I set out on my career transition journey, the only thing I really knew was that I wanted to find something more fulfilling. I had no game plan, no defined path to follow. But as I look back on what transpired over the nine months of searching, I realized that there were three clear steps that helped guide me to my decision.

If you are feeling like a change is needed... ask yourself what you’d do if you won the lottery, outline the next two steps, and define your values - hopefully, that will help you find your way.