Tales of a Solopreneur: Plan Early for a New Year’s Success

by Richelle Lyn
published in Writing

I’ve discovered several advantages if I start to plan for the new year at the beginning of December: more time for my reflections and new ideas to marinate, I feel ahead of the game on January 1, and I’m more intentional with my time and focus in December. Rather than working double time to accomplish everything on my to-do list by December 31, I have better data to re-prioritize my task list and decide what’s worthy of a big year-end push; so, I can spend more time recharging during the holiday season.

This final installment of Tales of a Solopreneur explains how you can combine strategic planning for your business with your personal planning using my Reflect, Reboot & Re-prioritize (“RRR”) framework to set you up for long-term success and short-term fun.


Running a solopreneur business effectively requires an alignment between your mindset, skills, and determination. You can learn what you don’t know. You can develop your skills and double down on your strengths. But self-reflection is key to determining where you should be focusing your time, versus where you’re spinning your wheels or wasting your time. 

Spending one hour up front to reflect on the past year will help you more efficiently plan what steps you can take next year to move your small business forward without sacrificing your personal happiness and satisfaction.

The first step is to ask yourself the following questions about this year:

Completed Goals: Which goals did you complete, when, and how long did they take?

  • Did you finish them sooner or faster than planned? Were they time-sensitive, or something you loved to do or played into your strengths?
  • If you started them later or they took longer, why? Did other projects or self-doubt get in the way, or did you fail to plan right (i.e., underestimated how long things would take or failed to identify the action steps needed)?

Open Goals: Which goals did you start but not finish, and which goals were never started?

  • Why? What roadblocks did you run into?
  • Did timelines change, did the goals stop making sense, did you fail to plan right, did you get side-tracked with something else, or were your eyes bigger than your year and you just ran out of time?
  • Which goals do you want to do a final year-end push on, carryover to next year (“Carryover Goals”), back burner for a future year, or eliminate completely, and why?

Themes: Identify themes that keep popping up.

  • Did you complete the most important goals to move you and your business forward, or did you focus on the easiest goals because you were good at them, the other items were too scary, or you just wanted to check something off your list? 
  • Did you delay goals because you were undermined by your mindset?
  • How good were you at identifying smaller required tasks and estimating work time?
  • How good were you at staying focused?

Progress: What progress are you most proud of, and why? Do you feel like you could have done more, or did you have unrealistic expectations? 

Resistance: What was the toughest challenge, biggest surprise, and biggest disappointment you faced and why? 

Lessons: What did you learn about your business or yourself this year, and which was the hardest lesson you learned, and why?

3 Roadblock Busters: Make a list of three actions you can take to bust through your roadblocks. 

  • For example, do you need to start or stop something, to learn a specific skill, to hire an expert to complete a task that’s holding you up, to recalibrate your mindset, tips on developing an effective action plan, practice showing up and keeping a routine, or a reality check when setting expectations for yourself and others?

Your Wins: Celebrate where you are, what you’ve learned, and the progress you’ve made. Cue your happy dance!


The hard part is over. Now for the fun part. 

Cast Your Vision

I’ve discovered planning for my business and personal life together provides a more holistic life perspective and is a better gauge of what I can reasonably fit into a year. 

Spend 30 minutes brainstorming what you desire for you and your business. Be bold. Do not self-edit. Only you will see your answers. Start with these questions:

  • What’s your pie in the sky dream for you and your business?
  • Where do you want you and your business to be in 1, 3, and 5 years? 
  • What must you accomplish to achieve your vision? Is there a clear path forward, or do you need to design it? 
  • What’s your WHY (or why do you want what you want)? 

Claim Your Goals 

Now, review your vision answers, and identify the goals you want to complete by the end of next year for you and your business.

Your Business.

  • Top 3-5 new business goals that will move you closer to your vision.
  • Carryover Goals.
  • 3 Roadblock Busters.

You: Identify at least one goal from each category below to build balance into your upcoming year.

  • Passion project (e.g., start or focus on a hobby, sport, or nonprofit organization).
  • Physical and well-being (e.g., build and strengthen your health habits)
  • Social and relationships (e.g., build and strengthen your connections and community). 
  • Fun (e.g., add more joy, more often).


Finally, it’s time to re-prioritize your perspective and your task list and plan for next year’s goals. 

Adopt a Four Quarters Perspective

Focusing your energy and building your implementation plan on a quarterly basis provides you wiggle room to refresh and pivot throughout the year. 

  • Quarters Grid: Draw a four-box grid on a piece of paper and label the quadrants: Q1, Q2, Q3, and Q4. Assign your new goals in chronological order to the four quarters based on when you need/want to work on each of them. Limit each quarter to 1-2 big goals or 3-4 smaller goals, so you can maintain your focus and gain traction.
  • Bonus: Plot out your annual vacations and build them into your calendar and your four quarters now. It will give you something to look forward to, help you refresh periodically to avoid burnout, and help you be more realistic about what you can accomplish in a three-month period without sacrificing your time off.  

Plan Your First Quarter 

On a new piece of paper, prioritize each goal you assigned to Q1. Then, for each goal, ask: 

  • Milestones: Identify the 3-5 action steps (“milestones”) you must take to complete the goal. If you’re stuck, try working backwards from the last step you need to complete the goal until you get to where you are now.
  • Timing: Estimate how long each milestone will take to complete and then multiply it by 1.5 for a built-in buffer. 

On a separate piece of paper, write 1-12 down the left side and add the dates for each week in the quarter. 

  • Commitments: Note for each week the days you need to block out for previously scheduled work and personal commitments, such as school breaks, work travel, and scheduled vacations.
  • Weekly Targets: Assign your milestones in the order you plan to work on them across the 12 weeks, using your milestone time estimates and how many weekly hours you plan to devote to your goals. If you run out of weeks, decide which goal(s) to move to a future quarter.
  • Bonus: Build in days for you to brainstorm and strategize for your business, as well as days for you to decompress. Also, build in at least one buffer week to knock out tasks on lingering projects. 
  • Weekly Planning: Review your Weekly Targets for each new week and update them for your prior week’s progress. Consider what information, education, or resources you need to learn or acquire to keep moving forward on your milestones. Then identify which actions you will take that week. 

Refine Your Next Quarter

At the end of Q1, spend 30-60 minutes thinking about how your progress compares to your initial quarterly plan.

  • What did you complete? 
  • How close were your time estimates? 
  • What challenges did you face? 
  • What changed in your business that requires changes in your planning for next quarter?
  • Will incomplete milestones be carried over or eliminated? 
  • How do you feel? 
  • What are you excited about?

Repeat the ‘Plan Your First Quarter’ steps for the goals you initially identified for Q2 and add in any Carryover Goals you identified from Q1.

Repeat this ‘Re-prioritize’ step for Q3 and Q4.

Then restart the entire RRR process at the beginning of December for the next year.


I will be finishing my 2023 planning over the coming weeks. I can’t wait to see which business and personal goals I decide on and the fun activities ahead.

I hope you find the RRR framework helpful as you strategize for your business and decide where to focus your time and energy in 2023. And remember to celebrate your wins now and throughout the year. Keeping your eyes on your prizes is a great way to create your own long-term success and personal fulfillment.

genre identity crisis

Richelle Lyn is a compensation & benefits attorney and HR executive, who now spends her days focused on the writing life. Her favorite fiction reads involve leading ladies who push boundaries and conquer their fears while preferably digging for secrets, learning magic, and/or saving the World. She’s also a fan of non-fiction reads focused on personal growth and transformation. She loves her tea hot and her coffee iced. She calls South Florida home, but her favorite place to be is on a trip. You can check her out on Instagram.

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