Box Cutter Co.

How A Simple Thinking Practice Keeps My One-Person Business From Spiralling

A 10-minute routine for when you’re the whole company (and your brain wants out)

Author’s illustration created on iPad using Procreate

A one-person business always has an invisible constraint. There’s no buffer. There’s no team to absorb an off day. No one to “cover you” when your thinking gets cloudy or messy.

When you’re the whole company, your mind is part of the business infrastructure. (If it’s a creative business… it is the critical infrastructure.)

That’s why one of the biggest threats to a one-person business isn’t competition. It’s the business operator. It’s the internal thrash and crash. I notice this most when I’m balancing multiple lanes, including:

• My consulting work (Ghostwriting, designing educational content, building micro-credential courses, fundraising, organizational development work, etc.)
• My own creative work, including D. Loewen Strategy Co. and Box Cutter Co., and
• Humanity Academy, the educational social enterprise Co-founded with my wife Lisa. (links at end of story)

Different outputs, with similar bottlenecks: if I get reactive, the work turns into more thrash. Or, resistance shows up and tries to turn my day into avoidance. If I don’t manage my thinking well, my thinking and overthinking manage me.

If my thinking is reactive, the business gets reactive. If I’m scattered, the business gets scattered. If I’m avoiding, the business stalls.

“Thinking about thinking” sounds academic until you treat it like a key operating skill. A practice you can train, and a system you can repeat.

Here are four thinking tools I use to keep a one-person business steady, especially when the digital world speeds up.

Four Simple Thinking Tools For Your Business

1) Keep a “Thinking Journal”

This is not a diary. It’s a debugging tool. Five minutes a day. Three simple prompts.

• What happened today that mattered?
• How did I respond, and what story was I telling myself?
• What will I do differently tomorrow?

Over a few weeks, you will start seeing patterns:

• what triggers avoidance
• what makes you sharper
• what kind of work drains you
• what decisions you keep postponing

This sort of awareness becomes leverage in your business.

2) Schedule and use downtime like it’s part of the job

Most people treat quiet time as a reward. In my one-person creative business, it’s also a critical part of operations.

There’s a lot of talk these days about mindfulness. I prefer a simple definition: paying attention to what’s happening right now — on purpose.

I was recently reading “The Practice of Not Thinking: A Guide to Mindful Living” by Buddhist monk Ryunosuke Koike.

Author’s screenshot of the book

And he proposes a dead-simple way to be mindful: “If you find that you’re thinking unneeded thoughts, you should focus on feeling instead.” Meaning, focus on your senses and what’s happening with them. Bring awareness to them.

For me, I often do this through movement. My version of mindfulness in my work is a daily walk. Today, where I live in western Canada, it was a snowshoe in a fresh dusting of snow. 👇

Author’s image

I’m not looking to “get better” at walking. I don’t have a daily step count or weekly mileage goal. I generally walk the same stretch of rural gravel road. I track my walks in the fitness app Strava — but more out of curiosity and motivation to stay active.

Last year, I walked over 1500 km (almost 950 miles).

Often when I’m walking and not actively thinking, fresh ideas and solutions to challenges arise. Frequently and without fail. Walking allows your mind surface what it’s been hiding under “productivity” or “being busy.”

Give it a try. Before you set out, ask one question and stay with it:

• Why am I thinking this way about this challenge?
• What’s the simplest next move I keep dodging?
• What am I avoiding admitting?

Doing this trains your attention and awareness. That’s a deeply valuable business skill. I use my phone to dictate quick notes into the Notion app.

3) Use the “5 Whys” when you feel stuck

When you hit a little friction, don’t jump to tactics to fix it. Go deeper, to find the causes. To do this, ask “Why?” at least five times. Each answer becomes the next question.

You’ll usually uncover something like:

• fear of being seen
• fear of being obvious
• perfectionism dressed up as standards
• a vague goal you don’t actually believe in

Once you name the real cause, you can act like an adult about it and start making the changes.

Author’s illustration

4) Run “What? — So What? — Now What?”

This is the fastest debrief I know. We use it for our business talks regularly. It can also be powerful in looking at the latest idea you have. This simple yet effective exercise helps you delve deeper into your thoughts, decisions, and actions.

Three steps:

1. What? — This identifies (and recognizes) a specific action, event, or decision. It’s about being aware of what has happened or what you’ve done. Stick to the facts.
2. So What? — This is the reflection stage. Consider the implications, effects, and importance of the event or action. It’s about understanding the impact of the ‘What?’ on you, your business, and others. Don’t be afraid to name some emotions in this.
3. Now What? — This is the forward-looking component. Based on the ‘What?’ and ‘So What?’, you now plan and decide what to do next, how to respond, or what actions to take.

This exercise can be a game-changer. It’s a systematic way to dissect experiences, reflect on them, and then use those reflections to inform future actions.

It’s critical to remember that “data” is always 100% based on the Past. Data-informed decision-making is important; however, it can never predict the future. The future is always uncertain.

The “What? So What? Now What?” exercise is a great tool to equip one-person businesses (and even large organizations) with navigational tools for the uncertainties of the future

You can also use it after challenging circumstances, like:

• a messy client interaction
• a week where you didn’t ship
• a produce launch that flopped
• a decision you’re second-guessing

It helps turn emotions into options, choices, and direction.

Author’s illustration

A Simple Weekly Ritual

Pick one slot each week (Sunday evening or Monday morning).

1. Review your Thinker’s Journal highlights
2. Identify one pattern you want to change this week
3. Choose one “Now what” action you’ll execute within the next two days

Your one-person business probably doesn’t need more hustle. It most likely needs steadier, clearer thinking. Because when you’re the whole company, you’re always building two things at once:

(1) the business, and (2) the mind that runs it.

This story is based on Day 5 of a Free 5-Day Email Course I created called: **The Solopreneur Thinker: 5 Days to Master “Thinking about Thinking”** Sign up is simple. No spam, no trash.

Interested in more Free 5-day courses? Lisa Loewen, MAIS, RCC, and I have created several at Humanity Academy. We also have a publication here on Medium.