Success in business often comes with a steady focus on the road ahead, but taking time to reflect and celebrate wins is just as important. In Entrepreneurial Trinity, Brian and Mary Joe share how creating moments to pause and recognize achievements contributed to team morale and personal motivation.
Celebrating the Highs
“Mistakes can feel like lows in the flow of business. Since it was important for us to create a positive work environment, we tried to remember to celebrate the wins whenever possible. In hindsight, I likely could’ve been much better. Like many entrepreneurs, my eyes were often focused down the road, so I didn’t take as much time as I probably should’ve to celebrate.
We had a Christmas party every year, our annual retreat, dinner to celebrate our anniversary, and occasional happy hours. These events are a great way to get together in a setting outside the normal work environment, and they were also a very organic way to see the growth in the company and the team.
Our first Christmas ‘party’ was just Donna and me saddled up to a bar watching football. Although it was somewhat impromptu and very economical, it gave us a chance to look back over the year, laugh at some of the tough times, and talk about the recent momentum. It really gave us tremendous energy for the new year ahead. As the years went on, the Christmas party continued to have a casual feel but grew into more organized events in classier establishments. It was always fun seeing the increased size of the group over the years through the eyes of our team’s significant others, as was watching the progression of the relationships as younger team members would bring their boyfriend/girlfriend one year, only to arrive just a few short years later with that same person as their spouse.
In day-to-day work, I would sometimes lose sight of that, but these parties were always great for highlighting the personal growth of the team.
For our first anniversary dinner, we went to our favorite local steakhouse. It was a table for four: me, Mary Jo, Donna, and her husband, Vinny. It was a great night, but the company was far from a thriving business, so it was a tempered mood, at least for me anyway. By the time we were celebrating our third anniversary, we needed to use a private room at that same steakhouse. For the fourth anniversary, we couldn’t fit in that room, so we needed to use their larger private room. By the fifth anniversary, we had outgrown the intimate steakhouse altogether and needed to look for a new venue, one of the many consequences of growth.”
Celebrating milestones, big or small, fosters camaraderie and provides moments to reflect on how far you’ve come. Whether it’s a casual holiday gathering or a more formal event, these celebrations are not just about the company’s growth—they’re about recognizing the personal and professional achievements of the team that made it possible.
Find inspiration in more stories of business growth and leadership in Entrepreneurial Trinity.