7 Essential Steps I Take Every December to Prepare My Business for the Upcoming Year

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The Annual Ritual: A Small Business Owner’s Guide to Reflection and Planning

As we step into December, the air thickens with anticipation for the upcoming year. This month isn’t just about holiday cheer for many small business owners; it’s also a critical time for reflection and strategic planning. After running a small business for over two decades, I’ve developed a routine that helps keep my priorities straight, holds me accountable, and fosters connections with my team and clients. Here’s a glimpse into my annual ritual that guides me through the transition to the new year.

Employee Bonuses

As the year draws to a close, I make it a priority to express my gratitude to my team. Each employee and contractor who plays a vital role in my business receives an evaluation and a discretionary cash bonus. This isn’t your run-of-the-mill bonus; it’s a reflection of our collective effort and a gesture of appreciation. I ensure that these bonuses are never less than what they were the previous year unless financial circumstances dictate otherwise—a scenario I’m fortunate to have avoided.

Delivering these bonuses is a personal affair. I slip each bonus into a holiday card, complete with a hand-written note, and send them out traditionally through the mail for that extra touch of sincerity. For remote employees, I still maintain the personal touch by sending their bonuses electronically alongside the physical card. This thoughtful act not only uplifts morale but also strengthens the bonds we share in our virtually connected team.

Employee Evaluations

Rituals extend beyond bonuses. Since my business is entirely virtual with team members spread out globally, traditional holiday parties are off the table. Instead, I conduct informal evaluations to check in with each employee. This provides a platform for constructive feedback, ensuring everyone knows where they stand as they transition into the new year.

During these evaluations, we set specific goals for the upcoming year—be it chargeable hours, client service ratings, or educational achievements. Clarity in expectations helps my team benchmark their performance and fosters a motivating atmosphere that embraces growth.

Gifts

The end of November marks the beginning of my gift-planning phase. I take time to compile a list of individuals—clients, suppliers, partners, and media contacts—who have supported my business throughout the year. Each person receives a token of my appreciation, typically chocolates or a gift basket, all within a budget of about $35 per person. It’s a manageable expense for around 50 recipients, but the joy it brings me, and the gratitude I receive in return, make it worthwhile.

This tradition not only allows me to express thanks but also reinforces the importance of maintaining relationships with those integral to my business journey. Each acknowledgment is a reminder of the collaborative effort that fuels my entrepreneurial venture.

Forecasting

Instead of a strict budget, I prefer to create a business forecast, staying grounded in reality while also remaining aspirational. I craft an online spreadsheet to guide my financial outlook for the year. During this time, I evaluate compensation and adjust other crucial costs, honing in on quantifiable business goals like client project completions and new revenue targets.

This process equips me with a clear vision for what’s achievable in the coming year. Transparency in my financial expectations minimizes surprises and enhances my ability to strategically navigate through the opportunities—and challenges—that lie ahead.

New Year’s Resolutions

Although often viewed as cliché, New Year’s resolutions can be profoundly empowering. I take the opportunity to set personal and professional aspirations for the upcoming year. For instance, one goal is to make quarterly visits to meet my remote employees in person, reinforcing our connections despite geographical distances.

I also plan to delve deeper into AI technologies, exploring how they can be integrated into our existing operations to enhance efficiency and gain an edge. By embracing uncomfortable projects that push my limits, I seek out challenges that promote growth and keep my entrepreneurial spirit engaged.

Personal Goals

Equally important to my professional aspirations are my personal goals. Each year, I weave in objectives surrounding health, leisure, and family bonding. Whether it’s maintaining a balanced weight, pursuing hobbies, or traveling to new places, these aspirations act as pillars that support my overall well-being.

I’ve enjoyed exploring foreign lands with my wife, working remotely in unique locales, which adds a thrill to our routine. These goals keep the fun alive while also ensuring that downtime is considered alongside the hustle of entrepreneurship.

Documenting Progress

The heart of my annual planning process lies in accountability. I take the crucial step of documenting my goals and plans, adding reminders to my calendar app to “check in” on my progress at the end of each quarter. This system provides not only a reminder but also a structured opportunity for reflection.

As the year unfolds, I look forward to these check-ins. Seeing where I’ve succeeded and where I’ve fallen short encourages me to reassess and recalibrate my strategies. Storing these reflections gives me valuable insight into my growth journey over the years and adds a layer of perspective to the challenges I’ve faced.


This is a living blueprint that continually evolves, shaping how I reflect on the past while preparing for the future. If you’re a fellow business owner, consider adopting a similar approach; it cultivates clarity and focus, paving your way to a more fulfilling, organized year ahead.

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