My Unimpressive Yet Very Effective Approach to Time Management as a Solopreneur

I hesitated even writing this post because the phrase “time management” is so profoundly colorless and boring I want to slap myself just to feel something again.

That said, recent conversations have led me to believe that, despite all of the breath wasted on time management and workflow, freelancers and consultants still have a Goldilocks problem. The proposed methodologies (another yawn-inducing word) are either too hot or too cold, never just right.

My hunch is that recent inflation, political turmoil, violent conflicts, and market choppiness due to AI have made it harder for freelancers, consultants, and agency founders to focus. We have these extra concerns on top of run-of-the-mill ones, such as bills, health, and client antics.

I’ve had my struggles with anxiety, especially about money, and I’m easily distracted when I’m not hyper-focused—both tell-tale signs of ADHD I’m told.

So, though I won’t say my approach is just right for everyone, I’m confident in saying that it has worked well for me for years now. Beyond helping me bring structure to my days, it keeps my optimism in good trim.

How we work affects both how we feel while we work and how we feel at the end of any given day. Those feelings bleed into the rest of our lives. Even if I finished a bunch of stuff, an incontrovertible fact, I can still feel like the work day wasn’t well spent and fruitful. Feelings can change the stories we tell ourselves from true to false. Feelings can distort reality.

Working the way I’m going to show you thus has two benefits:

1. I feel satisfied at the end of more work days, and

2. That qualitative result happens because I focus on what I can control, not on what I can’t—inputs, not outputs.

This focus doesn’t come easily to me, and neither does the practiced serenity that says, “What I accomplished will have to be enough.”

I arrived at the system you’ll find below after seventeen years of wrangling undiagnosed ADHD, making a respectable six-figure freelance income most years, and spending six or more weeks out of office on average.

You should know that this system, if it even qualifies as that, is less like a majestic ship of the line built ground up from a detailed design and more like a blockade runner assembled from salvaged parts.

The parts consist of banged-up, secondhand ideas, guidelines, and practices I tried after accidentally cutting myself with much shinier tools.

Prepare to be unimpressed and yet encouraged as you see how the parts of the system work together to create clarity, serenity, and felt momentum.

Table of Contents

1. Assign only 80% of your capacity.

2. Plan the full week on Sunday afternoons.

3. Match tasks to energy.

4. Plan blocks and breaks—and be realistic about it.

5. Theme your days.

6. Make more rules.

7. Schedule thinking time.

Closing Thoughts on Productivity Versus Fruitfulness

1. Assign only 80% of your capacity.

My friend Brett once asked me, “What would it look like to only book yourself at 80% of your capacity? Would that leave you with more margin to respond with grace to things that come up?”

Yes, it would. And it has.

I applied Brett’s 80% rule of thumb in a straightforward way: I put fewer tasks in my to-do list each day than I believed I could finish. I deliberately left the turkey understuffed.

Nothing in life is more predictable than curveballs, and the last 20% I hadn’t assigned to a specific task left me with margin when life happened—for example, a call from the kids’ school because one of them is sick or a planned-for tasks taking me ninety-three minutes instead of the forty-five I had estimated.

Even though I’ve been freelancing a long time, I still miscalculate, and the 80% rule gives me a more honest, realistic, and flexible way to think about and respond to the organic, evolving nature of my relationships, projects, and needs.

The last 20% is my agreement and alignment with reality: I usually underestimate how long certain things take and overestimate what I can fit into a day.

2. Plan the full week on Sunday afternoons.

Every week brings a fresh sack of cats, that is, a yowling, scratching, unpredictable mess of problems, needs, and deadlines.

If I open the bag on a Monday morning, right as I’m supposed to get to work, chaos ensues. It won’t all fit into one day. What should come first?

The easiest fix I’ve found is opening the bag before I feel any pressure and to use questions to decide what ought to go where and when: What is already in my calendar? Do I have any real deadlines? What are my unfinished client projects? Where will I make room for my own marketing commitments? Spoiler: Every morning. What about my writing practice? Also every morning.

Once I begin to see which time slots are already taken, I can see which ones are left for tasks that have no strict timeline: What’s on tap for the Freelance Cake Community? Which projects will create a logjam and stress next week if I don’t hack through several big pieces of work this week?

Unlike cats, each of my projects has dependencies. This task is waiting on that decision, and that decision is paused until the client answers three questions, which they seem to have forgotten in the crush of commerce. I need to send a reminder on Monday.

Yes, such dependencies create a go, and stop, and crawl forward version of progress, and because I’ve been doing this for a while, I can anticipate the delays and do what is within my power to prevent them.

It takes extra effort to help clients get out out of their own way and thereby provide a better experience for them, but that’s part of what they’re paying me for—and another reason to charge premium prices.

I safeguard my own satisfaction by seeing the connections and chokepoints and looking for ways to turn inertia into momentum across the week. Proactive project management can look as simple as a Slack message.

Projects are always trying to stall, and planning the week in its entirety allows me to be more strategic in how I allocate my time and nudge cats (aka, clients): call the one who went dark (to get the needed approval), draft the podcast questions using a voice memo while I’m in the pickup line at my kids’ school, schedule Wednesday’s follow-up email on Monday.

You can accomplish more each day without feeling rushed if you plan your weeks.

3. Match tasks to energy.

My best creative hours happen in the morning. Hot black coffee. The blissful absence of my children, at least when school is in. The whole day in front of me. You know the feeling.

Certain tasks deserve my most lucid thinking, my undivided attention, my imagination frolicking in possibilities like a cosmic dolphin. Strategy comes to mind. The type of work that really should be generative and expansive. The reality checks and common sense can come later.

Writing first drafts of essays, stories, and a client’s copy also comes to mind. My better ideas appear with the morning dew like mushrooms.

Can I reply to emails in the morning? Well, sure.

But those morning replies tend to be longer and more robust than they need to be as the beautiful creative impulse finds an outlet. Email is a waste of that quality of attention and energy, and worse, my inbox gives my mind the very thing it doesn’t need—distractions.

I can lose an entire morning to writing excellent, award-winning emails that people give the same cursory read as average ones and to chasing neon squirrels across vast expanses of internet. They disappear up a tree, and I wake up wondering how I got here.

Some types of work don’t deserve my richest attention. Afternoon emails would have been sufficient.

So my best work and most valuable contribution to my own business, to the Freelance Cake Community, and to my clients’ projects comes when I strategically punt operational and administrative tasks to after lunch.

Or, if I make time for any of these piddling tasks, I’m treating them as pebbles, Stephen Covey style, and sandwiching them between rocks. Five minutes devoted to answering text messages is a helpful reset when I do it between two important ninety-minute blocks of hyper-focused effort.

Either you match your richest attention with the blocks of work most deserving of it, or you end up with afternoons like I’ve experienced where you’re rushing to write something new or hit upon a perfect concept and it’s as easy as squeezing blood from a stone.

4. Plan blocks and breaks—and be mindful of the story you tell yourself.

What I mean by a “block” is a focused effort lasting sixty to ninety minutes. Breaks last five to fifteen minutes and consist of a walk, bio break, coffee refill, calls, texts, messages, or other form of greasing the business gears.

The block-break-block-break cadence imparts a pace and sense of momentum, and the weekly planning and energy matching make it easy to see what I need to accomplish and where certain blocks should fall.

For example, I know immediately that typing up a handwritten draft deserves a Tuesday afternoon slot, not a Monday morning one.

Picture your calendar. Each day is a square, and four or five rectangular Jenga pieces will fit inside. Each week your five squares can accommodate a maximum of twenty-five Jenga pieces, or blocks. You can fit two or three of them into each morning, matching the energy and attention appropriately. You can fit two or three blocks into each afternoon.

This is how I think about a week of blocks and breaks while remembering that I will have meetings or appointments on some days and will therefore have room for fewer blocks.

Also, despite my best efforts to plan, some days won’t go according to plan. I may have to make a mid-afternoon judgment call about which block I will push to a different day. I find myself asking the same question a lot: “What is most important right now?”

The blocks and breaks framework has that built-in flexibility and durability, and it sounds so simple that it can’t possibly work. Yet, it has for me for years. If I don’t want to work longer hours or on the weekends, then I have twenty to twenty-five blocks to work with. If I open the bag of cats on Sunday afternoons, I can see what is important while I’m removed from the work and clear headed.

I can match pieces of work to the type of attention and energy they need and go into the week with a firm grasp of what I must accomplish, when, and why. I don’t waste time lollygagging or casting about for priorities.

I also worry about whether I’m working on the right thing, or if I’m forgetting about something more important. Why?

I’ve learned that my Sunday afternoon discernment is better than my Wednesday-at-9:17am discernment. I know I can trust the plan I made. I can keep shushing my squirrel mind and tell it to focus on the very next block.

My misjudgments don’t wreck the plan because, as I already mentioned, I only schedule 80% of my capacity. A week can contain closer to thirty blocks, but I only plan for twenty-five.

If you think about it, true fruitfulness comes down to working on the right things at the right time. No one has thirty blocks of equally important work and not enough slots for them. No one.

The story we tell ourselves about there not being enough hours in the day is really a statement: “I overcommit because I forget what is most important.”

There is always enough time for what’s most important, and you will meet your most important commitments if you break them apart into twenty pieces of work and put those pieces in a sensible order.

Will everything get done? No, and doing everything was never the point. We don’t do our best work by doing everything. We do our best work by gauging importance with increasing accuracy. Fruitfulness over productivity. Pruning over complexity. Growth by subtraction.

5. Theme your days.

My current themes are as follows:

1. Monday - Deep Work
2. Tuesday - Blocks and Calls
3. Wednesdays - Deep Work
4. Thursday - Relationships and Calls
5. Friday - Relationships and Friday Zero.

Most days include four or five blocks of work, but depending on the day and its theme, I batch certain types of work. For example, I schedule coaching sessions back to back on Tuesday and Thursday afternoons. Catching up over coffee or lunch, in person or virtual, happens on Thursdays and Fridays. Most morning blocks I spend either on writing or strategy work or the odd block that’s difficult to schedule due to time zone differences.

On Wednesdays I schedule nothing except twice-monthly meetings with my mastermind group. I eat lunch at the same time, which leaves Wednesday blissfully clear. I can work without interruption or context switching and catch up as needed.

On Fridays I have a practice I call “Friday Zero.” I tie up loose ends in my planner, reassign unfinished tasks to new days, process all emails and get to Inbox Zero so that I can sail into the weekend, knowing that I have swabbed the business deck.

Theming has another benefit worth mentioning: saying no more often. I simply have fewer openings for meetings, which means I turn down more of them, which means I have fewer of them—all while moving projects and collaborations forward with a message.

“Hey, Richard, I don’t have availability on Friday afternoon [because I don’t take any meetings after 1:00pm, but you don’t need to know that] so how about this… Ask your questions here in this thread. I’ll answer them promptly. If we run into some problem that only talking in real-time can solve, then we’ll get something in the calendar next week. What are your questions?”

That unanswerable question or insurmountable obstacle never appears, and aren’t I glad that themes, especially Deep Work and Friday Zero, shrank my availability!

I like the work more than I like to meet to talk about the work. Maybe that makes me unusual.

6. Make more rules.

Rules (and deadlines) get a bad rap. I might not always like them, but I respect them as tools that simplify time and workflow management.

Here are several examples:

• Don’t check email until 11:00am. Do I even need to elaborate?
• Don’t schedule meetings before 11:00am. Aside from exceptions I make for coaching clients in European time zones, I reserve weekday mornings, 8:00am to 11:00am, for writing and my Morning Marketing Habit.
• Don’t send emails on the weekend. Notice I wrote “send,” not “reply to.” If Friday Zero doesn’t go as planned, I may spend an hour on a Saturday morning tidying up my inbox. I schedule replies to go out after 11:00am the following Monday so that I don’t give clients the impression that I have availability and want their replies on weekends.
• Don’t schedule meetings after 5:00pm. Again, I can think of rare exceptions, such as lining up a call with friends in Australia, but as a rule, my last meeting ends by 5:00pm. The rule leaves me with half an hour for my daily wind-up ritual.
• Don’t schedule lunch or coffee meetings except on Thursdays and Fridays. My Thursday theme includes relationships, and seeing friends during the week is one perk of the freedom and flexibility that freelancing affords. Too many coffees and lunches, however, and I find that the pleasant conversation and drive time has an adverse effect on my weekly plan. By not scheduling conversations that may run long Monday through Wednesday, I find a balance between friendship and life outside of work and the need to maintain my focus and generate income for my family.

7. Schedule thinking time.

I have written at length elsewhere about how entrepreneurs, business executives, and leaders of all types across two millennia have stressed the importance of thinking time.

Distractions and details guarantee that our days are consumed with fire fighting not solitude, and we give our best ideas and insights no opportunity to catch us. Everyone from Marcus Aurelius to Sara Blakely has found that intentional interludes of focused thought don’t happen on their own. We have to find time to think. We have to schedule thinking.

How telling it is that people without electricity, mobile devices, media, social platforms, television, the internet, email, or messaging apps have found it difficult to do this.

That puts us moderns at a disadvantage, or perhaps it’s more helpful to say that people who go to the trouble to schedule thinking time have always had a significant advantage over people who don’t.

The more time I spend thinking, the better my judgment is. Better judgment is better business.

Better judgment leads to better discernment, and I’ve found that taking a step back from my business often gives me the perspective I needed to notice an easier way to do something.

We turn time and workflow management into a feat of strength and balance and end up exhausting ourselves when a few moments of asking, “Is there an easier way?” can turn up ideas and options with surprising regularity.

Some doors don’t seem to exist until you walk back from the wall twenty feet.

Harvey S. Firestone, founder of Firestone Rubber and Tire Company, had two favorite questions for evaluating his company’s operations: “Is it necessary?” And “Can it be simplified?”

Scheduled thinking time and a key ring of good questions brings the unlock that we all want.

Closing Thoughts on Productivity Versus Fruitfulness

Most of our problems with time and workflow management have a root in our beliefs about productivity. The words we use are important, and I don’t believe that we are producers or that we have as our primary aim in work production or productivity.

We work for income and for pleasure. That work creates real things, whether turnips grown or gutters cleaned or IT systems maintained or words like these organized on a page.

Plenty of worthwhile work doesn’t fit into some great enterprise or capitalistic clockwork mechanism. Plenty of work isn’t productive in the sense that the results are measurable or immediately beneficial. Thinking about therapy, parenting, or coaching.

Think about thinking, for goodness sake. Is thinking productive? What KPIs and OKRs does it support? Thinking defines record keeping, yet clarity, confidence, ideas, insights, and decisiveness are precisely what many freelancers and consultants need more of.

My point is, the most important work is, by its very nature, slow, accretive, and difficult to quantify.

I have often missed this importance as I crushed through a long list of to-dos only to end the day feeling dissatisfied. I stayed busy, and yet I failed to make meaningful progress on the one or two most important things. I was productive, but I wasn’t fruitful.

Productivity puts the focus on efficiency and quantity. Fruitfulness puts the focus on efficacy and quality.

I’ll say, too, that the idea of fruitfulness brushes against identity. We’re creatures, not machines. We’re beings, not doings. Our value to our families, communities, and societies exceeds our output. We are not our work, though we can use our work to give a gift to the world, one that only we can give.

No matter what corporate doctrine may say, satisfying work and good use of our time has less to do with what can be measured and more to do with what can’t—curiosity, joyful exploration, mastery, and a deep connection to other people.

What could be more drab and sad than relentless productivity, a body turned into a battery or a machine? That sounds like hell to me.

When you’re ready, here are ways I can help you:

1. ‍Freelance Cake Community. Build the business you really want with people who really get it
2. 1:1 Business Coaching. Gain clarity, confidence, and momentum in your freelance or consulting business.
3. Free Money. A pricing and money mindset guide for freelance creatives. If you’re unsure about your freelance pricing, this is the book for you.
4. Morning Marketing Habit. This course will help you build an “always be marketing” practice, become less dependent on referrals, and proactively build the business you want with the clients you want. My own morning marketing habit has enabled me to consistently make 6 figures as a freelancer.
5. Smart, Strategic Pricing Bundle. For setting freelance prices you’re really confident in - priced meant to be so laughably low that you think there must be some mistake.