Welcome to the Amplify Your Journey March Spotlight!

I continue to be in awe of the powerhouse leaders I have the privilege of featuring—executives shaping organizations, business owners forging their own paths, and those rare individuals who navigate both worlds while also showing up for the people who matter most.

This month’s executive and business owner powerhouse, Dan Wood, is one of those exceptional leaders who seamlessly balances the weight of both roles: a dedicated attorney and a business owner. With sharp legal expertise, a strong entrepreneurial spirit, and a steadfast commitment to his clients and his family, he exemplifies the perseverance and adaptability it takes to succeed in both arenas.

The ability to lead, build, and care for others all at once is no small feat. While not everyone has the same flexibility or support to do so, Dan's story is a testament to the importance of using that privilege with purpose—leading with authenticity, showing up with intention, and making an impact that extends beyond his work.

Dan's work is not just about business—it’s about service, integrity, and making a difference. Leading with humility and resilience, he proves that success isn’t measured solely by the size of an organization, but by the dedication and heart behind it.

Join me in learning about and celebrating Dan in the drive, passion, and purpose behind the incredible contributions he makes to his community every day.

Background — Tell us a little about your entrepreneurial journey.

What inspired you to own your own business? 

I have been a lawyer for thirty years. Twenty-one of those years have been as an entrepreneur and small business owner. I’ve come a long way from the Boston Globe paper boy who delivered papers to about fifty houses in my Boston neighborhood everyday before school. But as I look back on that now, I realize that those years as a hard-working, independent paper boy were the foundation for what I am today.

For the first nine years of my legal career I worked for a large firm, which had its benefits, but it wasn’t long before I realized I needed more. Or more accurately, I realized that I needed to improve the quality of my life. My wife and I were raising three young children at home, all under the age of five. It did not take me long to realize that these three kids, and my role as their father, were the priorities of my life. I was working long hours and commuting hours a day to and from my job. But these were hours that I knew I wanted to shift toward my family, rather than sitting in traffic just trying to get to work.

This realization, combined with the realization that my vision of how my legal skills should be utilized, led me to decide to leave my career as a “big firm” attorney and “hang my shingle” in a town near my home, where I could control the direction and mission of my practice and also spend more quality time with my family.

Balancing Act — What’s your secret to managing the demands of running a business while balancing caregiving (or how you’ve done so in the past)?

To me, one of the greatest life skills that any successful entrepreneur needs is the ability to maintain a healthy work/life balance. This starts with prioritizing what matters to you most and always staying flexible. Because my family has always been my priority, I made sure that if any of my kids had a school play or an awards ceremony, I would input their event right into my work calendar and work around it. If that meant that I had to schedule client meetings later that evening because I left work to watch one of their school plays, then that’s what I did. If I had to work on a Saturday to prepare for a trial because I left work early on a Friday to coach one of my kids’ baseball games, then that’s what I did. The key is staying flexible with your time and realizing that the work will always be there but your kid’s 4th grade play will only happen once.

Entrepreneurial Challenges — What unique challenges have you faced as a business owner, and how did you overcome them?

When my business partner and I first opened our practice, our biggest challenge was establishing a presence in the community and generating new business. At first, we accomplished this through the usual strategies: paper and online advertising, website marketing, and local sponsorships. However, if there’s anything I’ve learned about marketing over the last 20 plus years, it’s that the most valuable marketing is accomplished through the quality of your services and the “word of mouth” advertising that satisfied clients/customers provide.

The most difficult entrepreneurial challenge of my career, however, was the Covid-19 pandemic. At that time, the majority of my firm’s practice involved litigation, court hearings, and trials. My livelihood and business, which I had worked so hard to build over the years, was being threatened by mandated court closings. But rather than wallowing in self-pity, I realized that this was an opportunity, a pause, for self-reflection. I used this precious time to analyze my business, figure out what aspects of my business needed improvement, and implement those changes to ensure that the business would operate even better in the years ahead. That period of self-reflection also made me realize that it was time to pivot. It was time to adapt; time to be flexible. It was time to expand on the practice areas that were only a small percentage of our business before the pandemic, but had the potential for growth during the pandemic: real estate and Wills & Trusts. These practice areas not only thrived during the pandemic and saved my business, they also became cornerstones of my business in the years that followed.

Milestones — What milestone or proudest achievement have you celebrated in your business?

 Strengths and Successes — As an influential business owner, what are things you excel at? How about as a caregiver?

I think one of my greatest strengths, not only as a lawyer, but also as a person, is my sincerity – my ability to be honest and open with people and really listen to what they have to say. In order to help people, you have to genuinely care about them or about the issue or problem that you are trying to resolve. This quality is not only important as an attorney, but also as a role model to my kids. 

Another one of my strengths is my ability to take complex problems, issues, or scenarios and simplify them to their core to make them more understandable and/or manageable. I utilize this skill when presenting a complex case to a jury at trial or when clients ask me to explain how various trusts work. Some lawyers make the mistake of using legalese or fancy vocabulary to try to impress the jury or the client. I want them to understand me and trust me.

Which of the AMPLIFY pillars speak to you?

Accountability
Mindset
Plan and Parenting
Leadership
Innovation and Integrity
Future Goals, Flexibility, Moving Forward, Family
YOU (self-care) and your "Y" (Why)

Mindset – As difficult as it may be somedays, I always try to stay positive and not let setbacks change my outlook. One of the most important skills that I have learned over the years is recognizing that there is only so much that we can control at work and in our lives. And there is no point wasting time or energy worrying or stressing about things that are beyond our control. This doesn’t mean that we don’t try our best or hope for the best. This just means that we need to identify those things that we can’t control and recognize that everything doesn’t always work out the way we hoped, and that is just part of life. Don’t dwell on it or let it get you down. Instead, see if there’s anything to learn from it and keep moving forward knowing you did your best.

Parenting – Everyone loves their kids. Everyone wants to provide their kids with the best of everything. But some professionals make the mistake of thinking that making the most money and providing their kids with the best, most expensive material things are the best way to show them their love for them. This couldn’t be further from the truth.  The most valuable commodity in life is TIME. If you give your kids, your spouse, or your friends your time, then you have given them the most valuable asset you have.

Growth Areas — What’s one area you’d like to improve or a goal you’re focusing on for personal or professional development?

I’m in my mid-fifties now, but that doesn’t mean I’m still not learning or growing. I try to improve every day. In order to do that, I try to take some time every week for self-reflection. What can I do better? How can I be better? How can I improve my life? One of my goals this year is to try to be more selective in the people (the clients) that I choose to help and the problems I choose to take on. One of my weaknesses has always been having the mindset that I can, and should, help everyone with everything, regardless of its toll on me. That has sometimes come at the cost of unnecessary stress or feeling unappreciated. The fact is that not everyone is a good person, worthy of our time and our hard work. I plan to follow my instincts more when choosing my clients. There’s nothing more rewarding than helping a good person who appreciates your help.

Fun Facts — Tell us some fun or surprising facts about yourself that you’re willing to share with others.

Resources and Inspiration — Are there books, quotes, podcasts, or people who have inspired you or made a difference in your life?

I have a framed graduation card in my office at work that has been with me since I graduated law school: 

“Success” 

by Ralph Waldo Emerson 

“To laugh often and much; to win the respect of intelligent people and the affection of children; to earn the appreciation of honest critics and endure the betrayal of false friends; to appreciate beauty; to find the best in others; to leave the world a bit better, whether by a healthy child, a garden patch or a redeemed social condition; to know even one life has breathed easier because you have lived. This is to have succeeded.”

My advice to anyone considering entrepreneurship—be BOLD! Have confidence in yourself, in your ideas, in your product or service, and give it a try. I remember how nervous I was to leave the big law firm and start a small firm. I had a wife and three small children to support and I was afraid to fail. But then I realized that I had to bet on myself or I might regret it for the rest of my life. I knew that I would do whatever it took to succeed. That decision was one of the best decisions I have ever made in my life.

To contact Dan: 

Email: dwood@woodgresham.com 

Phone: (508) 503-1137

Click here or visit www.woodgresham.com

To send Dan a message on LinkedIn click here.

For more information on Amplify Your Journey executive coaching or to schedule your free goal identification and compatibility call, visit www.amplifyjourney.com/links or click here.

Stay tuned for next month's powerhouse spotlight!

For past spotlights and newsletters click here.

Thanks for reading,

Amy