The Enduring Productivity Hacks from 30+ Years of Self-Employment

9 key things that keep me sane and organized

Productivity hacks make the life I want to lead possible. They keep my stuff, my to-do’s, and my brain okay and in check.

Here are the ones that have stayed with me over time, supporting more than 30 years of self-employment and small business ownership. They each arrived in their moment, proved themselves, and continue to provide a gentle whirr of needed structure to all the things I want to work on and get done.

1. 43 Folders 43 Folders has stayed with me the longest. It’s an organization tool that requires 43 file folders, 12 of which are labeled with the months of the year, the others are numbered 1 through 31 representing days of the month. Each folder is where you store the non-digital things you may need for a particular day or month.

Yeah, some of us more than others still live on or with paper, hard-copy real-world artifacts that need to go somewhere, but even the mostly digital may have things like school forms, birthday cards, paper lists, back-of-the-envelope notes that need to go somewhere and not get lost.

What does this look like in action? At the end of the workday, I remove any contents of the numbered folder for the following day so I don’t forget what needs handling tomorrow. At the end of every month, I remove the contents of the next month’s folder and move items to the specific days of the month I’ll need to deal with those thing.

As examples: I have a flyer from Schwab that I keep in the “30” folder to remind me to do an end-of-the-month check on my accounts there. I keep a list of holiday present ideas on scraps of paper in the November folder so that as December looms into view I won’t forget that I already have some gift possibilities in the hopper.

The beauty of 43 Folders once you get into the groove is that your brain trusts that things are covered; it’s an excellent system for living with the ease that you won’t forget things. It simplifies life so much, in fact, that we’re an 86-folder family. I use the system for my work and personal projects and set up another one for our family that holds things like greeting cards purchased for coming occasions, bills to pay, camping reservations, events tickets, etc.

2. Getting Things Done Almost as old as my use of 43 Folders is everything I learned from David Allen’s book Getting Things Done*. While I no longer remember all I specifically picked up from GTD, I do know much of that book has been internalized and incorporated into my life and I’m better for it.

Here are four things I do know originated there:

  • Have a system for capturing all your ideas, all your projects, all your tasks, all your everything. Get it out of your head so it doesn’t overwhelm and distract you. 43 Folders helps with this. So does a task management application of your choice.

  • Have a system for reviewing your goals, your projects, your “someday-maybe” ideas, etc. to make sure you’re on track and that what you’re doing actually still matters.

  • Use the same systems for all areas of your life — having separate calendars and to-do lists adds a layer of unneeded complication. (I excuse my second 43 Folders from this rule because it is a system shared with others.)

  • If it takes two minutes or less, do it now. Don’t put if off or file it. There are three places I deliberately and most often put this one into practice: sorting the daily mail, social media postings, and organizing emails to reduce overwhelm. If an idea for social media pops into my head, I post it. If my email box is cluttered, I take the two minutes to delete junk and re-schedule emails (see #3 and #7 on this list).

3. Email Scheduling Before Gmail instituted their free version, I used Boomerang, but the idea’s the same. First thing in the morning and throughout the day, I reschedule emails so they stay out of my inbox until the time of day I work on that thing or the thing most closely related to it. I treat it as a digital 43 Folders too — rescheduling emails until next month or the day far in the future when I intend to deal with that thing.

4. ToDoist (or the right task managing program for you) I’ve used Outlook and Remember the Milk, but ToDoist is my current task management application of choice. Regardless of program, the most important thing is that you use it and how you use it so that it works for how you like to work and how you need to empty your brain for optimal flow.

Adding all my recurring tasks and appointments to the nth degree, for instance, was life-changing for me. Another thing I love and highly recommend for productivity that software makes easy (vs. a physical planner or paper list) is the ability to renegotiate with myself. That is, rescheduling tasks I didn’t get to or didn’t want to do on a given day.

5. Making Myself Right, Right Now That leads to a favorite concept of mine and a beautiful antidote to toxic productivity — making oneself right, right now. If something is not right, right now, especially in the nagging way of domineering productivity, I try to practice lowering the bar.

Yes, that’s lowering my standards until I feel that I and my actions and my feelings and my situation are okay, enough, “perfect” in their own way for the moment. I enjoy the resting and breathing easy that brings until I’m able to renegotiate my day and my tasks according to my normal standards and desired outcomes.

There is one stupid human trick I do in this area as a permanent practice. I always have an empty day in front of me (except for hard meetings and unexpected urgent to-do’s) and work from tomorrow’s task list. Whatever’s not done on tomorrow’s list at the end of the day gets rescheduled for other times in the week or coming weeks. That leaves tomorrow’s slate clean for me to work on the day after tomorrow’s list at my leisure.

6. Fault Tolerance When I used to moan about my business to the engineer-guy that is now my husband, he liked to say, “Wow! You’ve figured out perfectly how to run your business. Now it doesn’t work unless it runs perfectly.” Ouch!

Over the years I learned from him about engineering realism. Designing for failure. Life, projects, constructions, businesses, human beings ourselves — none of us, none of our contraptions (physical or abstract), none of it ever goes according to plan. You account for the absolute certainty of mistakes and failure through fault tolerance, by building in redundancies, cushions, fail-safes.

I knew that a business person was supposed to create systems, but I initially had created perfect systems that required perfection. Now I create the sort of cushion I need as part of the system. Where I need redundancy I have that, e.g., cloud backups of my most important files as well as local backups; paper and digital reminders of my most important things not to forget (one in a folder, one in the task program, and sometimes a third on a sticky note). #5 above shows how I build time and time buffers into my system. It still happens that I haven’t allotted enough time to get things done and that accounts for the reality of fickle or lazy moods here and there, but now I don’t feel bad about it. I renegotiate the deadline and add in the surplus needed.

7. The School Day Model (or the right scheduling template or concept for you) When I was a publisher, I often juggled up to 30 book projects at a time — some under consideration or in the works, some newly released and needing special marketing and sales TLC, and 20-some backlist titles that needed routine strokes to keep going. That life also involved managing employees, authors, freelancers, vendors, and a couple hundred customers, plus taxes, accounting, contracts, and a zillion other details I’m glad are now in my past.

Recently, thanks to books like Emilie Wapnick’s How to Be Everything*, Barbara Sher’s Refuse to Choose! Use All of Your Interests, Passions, and Hobbies to Create the Life and Career of Your Dreams*, and a bit of commonsense math, I realized that I don’t have to focus on only one thing. If I used to do everything from the paragraph above at once, I can certainly juggle the eight different things that are currently tugging at me at the same time. Sher’s Refuse to Choose gave me a name for the rough scheduling model I’ve been using: The School Day Model. Didn’t need the name but it sure is validating!

Right now I’m juggling one master’s degree class at a time, a return to freelance writing, project management/editorial work, coaching, adding mediation/ombudswork to my client offerings, an ecommerce business borne of the pandemic, closing down my publishing businesses, trying to set a couple community-oriented projects in motion, and figuring out how to participate in UBI advocacy.

Wait, is that 10 things, not 8? I also have a spouse, an 11-year-old, friends, and senior parents and in-laws. Hobbies, too. I think I have a couple hobbies.

The point is: I have a scheduling concept that works for me. I chip away at multiple things for a little bit of time each day and that suits me. My time slots are portioned out based on priorities, income requirements, best times for working, etc. They are not literally 45 minutes at a time before the bell rings, but it’s similar in practice: Work for the allotted time on the most important things in that category (or what the day’s energy permits), then move on. I’m restless on any given day — I want to indulge all my interests — but disciplined for the long haul. I know I have the patience and persistence to keep going as long as it takes as long as I don’t have to “compromise” daily by choosing.

Find your scheduling ideal or template and see if it doesn’t make everything better, easier.

8. Steve Chandler’s Morning Brainstorm One of Steve Chandler’s books on sales gave me a great tool for periods of stuck-ness or panic. Basically, it’s brainstorming 20 things every morning before the rest of the day starts. I think Steve’s was oriented towards sales ideas: Come up with 20 new ideas every day, then start with the most promising… I’ve used this for sales, but I’ve since adapted the practice to cover any area where I’m feeling stuck or where things aren’t working.

You don’t have to do it in the morning, but the routine can set quite a tone for the day. You’re reminded that there are always options. You’re reminded of the power of your own creativity. You’re reminded that picking the option/s with the most potential is, duh, an easier way to do things. Then, when you get into this habit, you learn that you can do hard things. The hard things that matter and produce the best results.

Then, one day, you realize that none of it is all that hard.

9. Hiring a Coach Finally, there’s nothing like hiring a coach to help you meet your goals, stay true to the things that matter to you, and stretch you on to new and bigger things. It can be so easy when you’re self-employed to get bogged down in your own busy-ness that you start missing the forest for the trees. A sign that you’ve found the right coach for you is that you don’t question whether or not the cost is worth it — it’s beyond apparent.

Not all coaches will comply, but I think it’s reasonable to ask for a free sample session (even 20–30 minutes rather than the usually 40–60) from a handful of coaches you’ve pre-selected on other criteria to get a sense of best personal fit for you.


A quick review

  • 43 Folders: A way to keep track of all the things on paper for exactly when you need it.

  • Getting Things Done: Read the book, sign up for the newsletter, internalize the lessons from the guy who changed the productivity game.

  • Email scheduling: Manage email by removing them from your awareness until the best time for you to handle them.

  • Task management app: Find the one you like best and play with it until you understand how to use its features to best organize life and work on your own terms.

  • Make yourself right, right now: Give yourself a break and learn this critical mantra and stupid human trick. Lower the bar so that you’re successful in this instant, give yourself a pat on the back, and build from there.

  • Fault tolerance: Engineers are flush with useful concepts that acknowledge the reality of mistakes, obstacles, and failures that we can adopt to join reality. Add redundancies and cushions to create robust systems that support you and not your idiotic expectations.

  • A scheduling template: Find a broad framework on which you can hang your ideas about how to use your time, spend your day.

  • Brainstorm your way out of stuck-ness and panic: Every morning, brainstorm at least 20 solutions to your biggest woe of the moment, then pursue the best idea on the list. You will soon know that there are always options and that you can count on your own creativity and grit.

  • Hire a coach: There is no better remedy for escaping the myopia and busy-ness that’s going nowhere. Assuming you’re doing the work, if it’s not blatantly obvious that your coach is worth the cost, you have the wrong coach.

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