Can you share a little about your background and how you got involved in financial planning?

I started my career with an accounting degree from the University of Massachusetts – Amherst and joined a small CPA firm in Westborough, Massachusetts. Working in a big corporate setting like the “Big Six” accounting firms didn’t appeal to me. From the start, I was drawn to work with small businesses where you get to see everything about a business and work directly with the business owner(s).

After a few years of auditing small businesses and preparing business and personal income tax returns, I left public accounting to work for one of the firm’s clients in the nonprofit sector. After three years, in 1998, I moved on to start my own business preparing taxes and consulting for small businesses.

Once I started working with small business owner clients more closely, it became clear that many of them needed advice about how to structure small business retirement plans.  Most small business clients did not have the necessary expertise to design and implement company retirement plans and, quite honestly, neither did I at the time. Also around this time I was approached by an acquaintance who was a commissioned broker.  He suggested that I consider selling financial products.  Although I didn’t yet have a full understanding of why, selling financial products did not feel right to me.

In the end, I felt I needed to both deepen and broaden my technical expertise to better serve my clients.  I decided to pursue a master’s in financial planning degree at Bentley University, where my eyes were opened to fee-only financial planning, the Certified Financial Planner® designation, and Dimensional Fund Advisor (DFA) mutual funds. The experience changed everything for me.

What led you to launch Milestone Financial Planning?

There was a clear need. Clients wanted trustworthy advice across retirement, tax, and estate planning, and I didn’t know where to send them. I had the tax background, and financial planning felt like a natural extension of the work I was doing. Helping people make better financial decisions across all areas is what drove me to launch my own financial planning and investment management firm in 2003.

What do you think makes Milestone’s approach to financial planning distinctive in a crowded industry?

Milestone’s approach to tax planning is one very clear differentiator which sets us apart from most other financial planning firms.  Income taxes are the largest expense most people will incur during their lifetimes.  Our team has deep tax experience that we bring to every aspect of the financial plan.

Another distinguishing feature is our diversity of ages and backgrounds. Many small firms consist of just one or two advisors and may not provide adequate succession planning. We’re not a large firm, but we still benefit from a multigenerational team, creating a better client experience.

It’s also important to highlight that Milestone is a fiduciary firm and completely fee-only.  That transparency builds trust.

Is there a habit, mindset, or practice outside of work that influences how you lead the company?

My motto is: “Always be learning.” I read everything I can, listen to podcasts, and study people who’ve built successful firms. That culture of curiosity is part of Milestone now. Our advisors constantly share insights and challenge each other to grow. Also, everything we do ties back to our mission of helping people, as that is the foundation of our existence as a firm. That clarity of purpose helps guide decisions big and small.

What is your greatest strength?

I’d say my work ethic and integrity, but it depends on whom you ask. My spouse says it’s how much I care and give to others. At Milestone, our mission is centered around helping people, so I’d like to think those qualities show up in the way we work with clients and support each other as a team.

Is there a particular turning point or milestone in the firm’s history that you’re most proud of?

Merging with Jean Fullerton’s firm, WJM Financial, in 2016 after our friend and colleague Bill Moeckel passed away was a huge moment. It was a painful and difficult time due to the circumstances, but we made it happen in just a few short months so we were able to support Bill’s clients. That experience taught me the value of compromise, partnership, and how different personalities can strengthen a business.

But I have to say I am most proud of our team today. We’ve worked hard to find the right people, mentor them, and build a positive, mission-driven culture. Working with this great group of talented people is incredibly rewarding.

What advice do you have for people seeking financial advice for the first time who might feel nervous or hesitant?

It’s a massive decision. You’re trusting someone with your life savings and to partner in financial decision-making. That’s a big deal. People say, “Just find someone you connect with,” but that shouldn’t be the only thing you consider.

Look for competence across the board, in investments, retirement, estate, and tax planning. Ask if they’ll help implement the advice, follow up with you, and coordinate with your attorney, CPA, or insurance agent. Implementation is where things often fall apart.

Also ask about succession planning. Many small firms don’t have a plan that is fully fleshed out or battle tested. We’ve implemented our succession plan three times, and we actively mentor the next generation. Continuity matters.

How has your approach to financial planning evolved as both the industry and your clients have changed?

Over time, I’ve learned that while the details of a financial plan matter, what really drives retirement success is more foundational, like how much you save, how frugally you live, how you manage risk, and having the right amount invested in stocks. Proper estate planning is also essential.

I’ve seen how unexpected life events can throw even the best-laid plans off course. That’s why I now focus just as much on risk mitigation, making sure that in addition to managing investments and their lifetime tax expense, clients have proper insurance and estate planning in place to drive their plan forward.

What do you hope clients take away from working with Milestone?

Peace of mind. We want clients to feel confident and secure about their future, not constantly worried about money. Different people experience different stresses around money; we work to ease the anxiety through education, planning, and empathy.

We’re here to walk with clients through all the milestones of life. After guiding many dozens of families to successful retirements over the years, we’ve seen that it’s not about beating the market, it’s about building a life with purpose.

What do you enjoy doing outside of work?

Honestly, I’m one of those weird people who loves reading about tax and financial planning in my free time and while at work. I find numbers calming.

Outside of that, I am focused on my faith, spending time with my family and helping others.

Jennifer Climo is the founder and CEO of Milestone Financial Planning, LLC.

At Milestone, we believe financial planning should be personal, thorough, and built to last. If you need help taking control of your financial future, please don’t hesitate to contact our team.