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Key Takeaways A long-standing annual ritual helps a small business owner reflect on the past year, clarify priorities and prepare thoughtfully for what’s ahead.
Through deliberate planning, personal accountability and meaningful connections, the process brings perspective, stability, and renewed focus without relying on rigid systems.
I’ve been running a small business for more than two decades. Over that time, I’ve developed some routines. One routine happens each year at this time. During December, I’m looking ahead and thinking of the next year. I make my plans. I make a few resolutions. I check in with those important. The actual details change each year, but the process is the same.
Here’s what I do every year, at the end of each year.
Employee bonuses
Before the year is over, I try to make sure that all of my employees and contractors who impact my business have been evaluated, connected and receive my appreciation. I send cash bonuses to each of them. It’s a discretionary bonus that I come up with every year based on profits and I’m careful to make sure that the bonus is never less than it was the previous year, unless profits are so bad that I couldn’t afford to make the payment (which thankfully hasn’t ever happened). Even in 2025, I’m doing these bonuses by manual check, which I slip into a holiday card that includes a personal note and is deliberately delivered old school in the mail. For a few remote employees, I do the bonuses electronically, but still send the card.
Related: If You Haven’t Already Done These 7 Things to Prepare Your Business for the Holiday Season, You’re Putting Your Business Behind the 8-Ball
Employee evaluations
Because my business is entirely virtual and many of my people are located throughout the world, I’ve stopped doing holiday parties. However, I make it a point to check in before the year is over with all employees with an informal evaluation just to make sure they’re getting good (and constructive) feedback and they know where they stand going into the next year. I take this time also to establish a few goals for the upcoming calendar year (i.e., chargeability, revenue generation, client service ratings, education certificates, etc.) with each person so they are clear how they’ll be evaluated in the coming year and can benchmark themselves.
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