No class taught this.
Kirsten and I just wrapped up another U.S. Chamber of Commerce Small Business Council Spring Meeting in Chicago at the Google HQ with over 40 business owners from all over the country – Washington to Florida and a bunch of states in between.
Two days of real conversations on business best practices, CEO real talk on the environment..tariffs, staffing shortages, burnout, border-state lodging impacts, and how AI can help us buy back time and work smarter.
But the biggest takeaway? Behind every business are families fed, vacations earned, and teams depending on leaders who keep showing up and leveling up. Having the hard conversations. Is the payroll system working? What benefits do you offer to ensure employee retention? How do you manage virtual work? What’s the best ROI calculator for service based businesses? How do we prevent burnout in a service based business?
For ten years, Kirsten and I have hit payroll every other week. Some seasons comfortable. Some seasons tight. We’ve never missed one. We offered profit sharing, healthcare, 401(k) match, work place flexibility, and kept every employee through COVID when there were mass layoffs. Our small company of 15 people held on.
Pressure is a privilege. The late night texts asking about cash on hand. The final push to sell tables before a gala that fund critical needs for law enforcement. The carefully crafted email to open a new prospect for funding needed to handle more cases. The member of Congress meeting that needs to happen before a crucial vote so our client’s voice is heard. The oped that needs to run to raise awareness on a complicated issue. The discipline we have to do it all despite the headwinds.
But it still feels like pressure and it’s rarely fun. Meeting other entrepreneurs in the same boat, fighting the same headwinds, knowing we’re not alone in this? Now that’s fun.
So grateful to the U.S. Chamber of Commerce for a seat at the table, Mekky Media for hosting us, and Couch Clarity for sharing your story.
Hard climb. Beautiful climb. Totally worth it.
– Kristen Sheehan, Founder and Partner
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