Issue #5, Volume 1
January 6, 2021
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As a kid growing up, I do not remember New Year’s Eves fondly.
Starting when I was in middle school, my mother insisted on a form of torture she called “writing resolutions.” During the afternoon of December 31, she would sit us all down around the dining room table with paper and pens and insist that we write down a specific number of resolutions.
It struck me then as an empty exercise, a waste of time, and a recipe for failure.
It still does.
I don’t believe resolutions work. I believe in planning. And there’s a big difference.
Planning requires 3 essential steps.
Step One: Review
Of course, the first step in planning is to look back and assess what’s worked, what hasn’t, and where you can improve. That’s true whether you’re talking about business, personal relationships, a website, or an exercise program.
Your tools for looking back will depend, of course, on what you’re evaluating. Common business tools include spreadsheets, financial statements, and the like. If exercise is important to you, maybe you keep a daily log showing whether you worked out that day, and what you did — how far you ran, biked, or swam, how much weight you lifted, or whether your team practiced or played and how it went.
For personal life, and just for general head clearing, journals make great planning tools. I don’t use anything fancy – just whatever plain notebook catches my fancy. But if you’re journaling to accomplish something specific, there are tons of subject-specific journals that provide prompts, outlines, and extras to keep you focused.
You’ll find gratitude journals, mindfulness journals, journals for wives/mothers/husbands/fathers, religious and spiritual practices, there are journals created as accompaniments to best-selling books.
Then there are the bullet journals. . . they have their rabid fans, but to me they seem like a lot of work. Here’s a good explanation of what they are (and aren’t), and if you want to see how carried away some people get with them, just check out the Instagram feed for #bulletjournaljunkies.
There are even books that tell you how to journal. One I like is Journal Your Goals: Prompts, Motivation, and Advice to Help You Achieve Your Dreams. (Full disclosure: the author cohosted The Anywhereist Podcast with me, and I’ve known her for years.)
Keeping a journal is a good way to give yourself something to look back on at the end of the year so you can figure out what you did well, and where you can do better. You need this information in order to plan for the future.
Step Two: Evaluate
Once you’ve reviewed your spreadsheets/logs/journals and whatever other tools are relevant for your business and your life, you’re ready to evaluate.
What did you do well? What could you do better? Did you stay true to your values, or did you deviate?
Step Three: Make a Plan
Chris Guillebeau created an easy-to-follow planning tool for reviewing, evaluating, and planning ahead, one that he follows each year. In How to Conduct Your Own Annual Review, he even provides his template for download. A couple years back, he wrote about how to conduct this annual review, even when you’re feeling sad. Given all the upheaval of 2020, you may want to read this before you dive in.
Business coach Chris Brogan has a different approach. Every year he chooses three words that best represent his values and goals for the year coming up. He keeps them in front of himself when he’s planning, and makes sure that his plans conform to those ideals.
Fizzle has created a useful tool, in the form of an end-of-year review process tailored to online businesses and solopreneurs.
Bonus: Be ready to adjust your plans.
These are uncertain times. There’s no “normal” right now for most of us, so flexibility and adaptability are more important than ever.
A Harvard Business Review article defined 4 levels of uncertainty:
- A clear future
- Alternate futures
- A range of futures
- Ambiguity
In his article Planning in Times of Uncertainty, Gautam Lohia noted that “not all uncertainty is the same,” and referred to those four levels.
“Most businesses today,” he noted, “are facing. . . a Level 2 environment of uncertainty,” known as the “alternative futures stage.”
“To tackle a Level 2 uncertainty we must follow a 3 step approach: examine, plan, and act.”
This requires you to review, and then to explore alternative scenarios for the future. Most of us have been doing this during the past 6-8 months, though maybe not intentionally. I know I’ve had to adjust in some unexpected ways, from cancelling a WordPress class I had planned to teach last fall, to restarting and reworking this newsletter as work-from-home and work-from-anywhere involve millions more people.
Some of my Favorite Planning Tools
Where do you write down and track your plans?
You could use a simple document or spreadsheet. Maybe a note-taking app like:
If you want to go beyond notetaking, a project management app might be just the thing. I’m a big Trello fan, so that’s what I use. If you’re part of a larger team, you might use Teamwork or Basecamp.
The important thing is the process, not the tool you use to keep track of it (although it’s easier if you’ve found a tool that you’re happy with).
7 Planning Steps Bridget Jones Can Teach Anywhereists

“Earth to Bridget Sodding Jones!” yells Bridget’s boss.
In the opening sequence of Bridget Jones’s Diary, lucky Bridget has been chosen to try skydiving — on camera — to see if it’s great fun or a terrifying risk. After being forced out of the plane, forgetting to pull the ripcord (prompting the above exclamation from boss) and finally drifting along, chute open, Bridget starts daydreaming about her boyfriend.
To come to earth with a bump — literally — facedown in a large pigpen.
Daydreaming while skydiving is not a fun combination!
If you don’t want to come to your senses, as Bridget did, in a large vat of metaphoric excrement, you need to do some planning.
Here are seven lessons Bridget can teach you about planning to create your best Anywhereist work and life.
Read: 7 Planning Steps Bridget Jones Can Teach Anywhereists
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