Letter to Leaders & Swenson Insights

Reflect - And Act - On Your Milestones

May is a big month for me. It’s my birthday month (and May 4, 2022 was a VERY big birthday).


May is also our wedding anniversary month.

Birthdays and anniversaries – milestones – are cause for reflection.


But reflection is only valuable if we use it to shape our future.


For me, milestones are transformational moments. I thought I'd share a few significant milestones in my professional life. It's not the milestone; it's the lesson.


  • February 2003. I'd been working with small businesses for a couple of years. I learned it doesn't take a genius to own a business. It takes hard work (and luck). Senior management wasn't for me. (Corporations still have many layers of management). Every day some boss told me what to do, what to wear, and where to be. I quit my corporate job and started a business with zero clients.

Lesson – nothing is above you in life. You can do whatever you want – whenever you want to.


  • June 2008. After working with an accounting firm for a couple of years, they made me an offer. Bring my clients and work for them and their clients. I declined (I’m not sure I can ever work for anyone else again). They came back with another offer. They acquired a part of my business and we created a sister company. Rose, Snyder & Jacobs provided business acumen and financial foundation that I lacked. It was a no-brainer back then, and it still is today.

Lesson – be clear about your weaknesses and find people to fill those gaps. If you spend all your time working on your weaknesses, all you’ll have is a lot of strong weaknesses.

  • May 2009. In the midst of the Great Recession, my business was hemorrhaging money. I couldn’t find a way to generate revenue. Bankruptcy loomed. A small insurance brokerage had been after me to start a ‘hotline’ service for their clients. I kept saying no; I didn’t know how I could staff it. Then one day, I had a revelation. We did that deal. That deal – 13 years later – remains a major reason I’m still in business.

Lesson – don’t offer people what you think they need. Instead offer people what they’re asking you to do. (This applies to every leader I know)

  • 2010-2012. Transformational clients. Through luck, connections, networking – whatever – we acquired several clients that became transformational:

  • A small bank that led to more banking clients. Then a national reach. Up until then, every bank I pitched asked, “but what other banks do you have as clients?”

  • A friend of a friend referred me to a Jewish Temple & School where he was the Chair of the Board. A year later, I had more connections to more clients. The relationships created were more personal than professional. Today, at least 15% of our client base is traced to that one client. (who we're still working with).

Lessons: The world is a small place. Everyone knows everyone, so every contact you make is a gift. You never know what opportunities lie behind each person you meet. Treat everyone who works with you (or for you) with huge respect; what goes around often comes around.

  • March 2011. I made a transformational hire and didn’t know it at the time! Still struggling during the recession, I hired a 15-hour a week assistant (it was all I could afford). Twelve years later, Jamie Baker is our Director of Operations. She is as much a reason – in fact, more - for our success as anyone. The best hire I ever made (and I’ve hired thousands of people).

Lesson: Every hire you make has the potential of changing your business, your future, and your life. Hiring then is the most important thing a leader does.


Happy May. Sometimes the smallest decisions have the greatest impact.


But whatever you do – make decisions. It takes courage.


Sometimes it’s accidental, but if there’s one lesson I’ve learned, it’s that making decisions drives success.


Reflect on your milestones. Not for nostalgia, but for understanding the decisions you still need to make.