Charting the Course: A Solopreneur Strategy for Life’s Many Hats

Juggling Business, Creativity, and Personal Life with a Practical Plan

Ever felt like a juggler with one too many balls in the air? Welcome to my world of solopreneurship, where planning isn’t just a business necessity; it’s a life raft in the ocean of chaos.

In the previous article, I discussed the problems of managing multiple life streams. The main lesson from the last twelve months was to resist the almost irresistible temptation to over-extend.

Disclosure. I use an AI assistant when writing. The assistant may suggest outlines, topics, or subtleties I had not thought of. The actual writing is all human me.

The image features a balancing scale with elements symbolising business, creativity, and family life. This visual encapsulates the essence of managing different facets of life as a solopreneur.
A Solopreneur Strategy for Lifes Many Hats Generated by DALL E 3

See more articles, posts, and discussions about business, project management, Generative AI and Creative Writing on Medium here. If you have not already, subscribe to Medium. Or follow me here on Substack.

The Journey So Far

This past week, I’ve been busy trying to be realistic with my planning, but I quickly found at least one over-optimistic decision, which has already been revised. This got me thinking about planning as a subject; a quick search returned dozens of one-liner quotes. This is my personal favourite for the context of this week’s newsletter.

Dwight D. Eisenhower: “Plans are nothing; planning is everything.”

The quotes were from various sources, including statesmen, philosophers, musicians, and authors, highlighting the universal understanding that while planning is crucial, the ability to adapt to change is equally important.

It is this willingness to adapt that is critical to successful planning.

Aligning Dreams with Reality

My overarching goals for the year ahead perhaps require some clarification. While they may sound simple when written down in a short list, implementing them all effectively may prove more challenging to predict.

  • Grounding Ambitions in Reality: Never over-extend and be constantly willing to adapt.
  • Cherish Personal and Family Time: A stable and happy personal life is vital for success.
  • Cultivate Creativity: Set aside fixed time blocks for my writing ambitions.
  • Sustainable Business Growth: Here, we have the most temptation to over-extend.

Here is my first attempt at a week of planning:

An Over-optimistic First Planning Attempt
An Over optimistic First Planning Attempt

The red time blocks are for contracted work, the yellow for creativity, and the blue for my business. All other times can also be considered one large time block; this is my personal and family time.

I’m writing this on a Friday morning but not as this planning suggests, starting at 6 AM. The mental energy expended for the four days of contract work meant, quite simply, that I needed a good rest and a reset before I would be ready to dive into either the creative or the business streams.

External dependencies will always impact any planning; we must be willing to adapt the planning to reflect new or unanticipated situations immediately. This is the revised plan:

The Revised Planning, hopefully more realistic
The Revised Planning hopefully more realistic

As you can see, I’ve already adapted the planning to reflect real life and practicalities. I could have forced myself to get up at 5 AM and push through the creative time block. But it would have been a masochistic waste of time.

I’ll illustrate how these goals intertwine personal aspirations with business growth. It all starts with a plan and self-discipline. And adaptability.

Business Management

No extra planning is needed for the contractual work scheduled every Monday to Thursday. Of course, within this work, detailed planning is required and executed with the help of ionBiz, Microsoft Outlook and Microsoft Teams.

For my business ambitions, marketing is the biggest problem. I’ve no experience at all with marketing; I’ve always been in a fixed-contract salaried position until very recently.

The Everyday Solopreneur: Navigating the Marketing Maze

I use Notion for all business-related activities, including creating and managing marketing strategies once I figure out which strategies I need. For the finances, I have a sub-license for Exact, which is all I need.

No doubt, as the business expands, I’ll have to reconsider whether the tools and apps I currently use are sufficient or need to be replaced or upgraded.

The Creative Engine

The creative time blocks total just six hours a week, not so much, but it’s a start. The intention is for these six hours to be devoted to long-form writing projects.

I’ve just realised I’ve forgotten to plan the time required for the newsletter. I have gotten faster with producing it, but it still takes three to four hours weekly. The problem, if you can call it that, is that I never plan exactly what the newsletter will be about. I prefer to wing it and see what pops into my mind at the time.

Half the time is spent researching or thinking things through; the actual writing would probably take only an hour and a half.

So now I have a problem, which I think I may have solved today with the help of Ikea. I bought a simple laptop stand that I can use in the evenings, so I don’t have to disappear into the home office and can spend time with the family instead.

We’ll see how this goes in the coming week. I’ll start scribbling the newsletter each evening. If I’m too tired, I won’t do anything, but if I have the energy and motivation, I should be able to get quite far before Friday swings around again.

Fortunately, inspiration is no longer an issue; I always find something to write about. It just means that the subject matter for the newsletters tends to wander around slightly or slightly a lot.

Such is life.

The Toolkit

I mentioned briefly the tools and apps that help me streamline these life streams in last week’s newsletter. This week, we’ll detail these and others not mentioned so far.



The only downside of this app is that it’s only available for Apple devices. The screenshots of my weekly plans were taken from Fantastical. An excellent review on Medium by Simon Theakston is worth a read.

How I use Fantastical on a daily basis across Mac, iPhone and iPad



Notion is my ERP app of choice. I’ve sub-dashboards for Creativity and Business/Marketing from my main dashboard. These contain two related databases, one for managing Projects and the second for Task details linked to the projects. I’ve also set up separate databases for other Projects and Tasks unrelated to the sub-dashboards.

The learning curve can be steep; for a great resource to start quickly with Notion, visit the YouTube channel for Thomas Franks Explains.



Another app that’s only available on Apple devices. I use it for anything and every short-form writing task you can think of, including:

  • This Weekly Newsletter
  • Marketing pitches.
  • Contract tendering.

If it’s short-form, Ulysses is the place to be.



Available for most platforms: both Apple Devices and Windows, although I prefer to work exclusively using my Mac. The slight differences in keyboard shortcuts, for example, irritate me.

All long-form writing happens in Scrivener, that is, over two or three thousand words.

Generative AI

I mostly use ChatGPT 4 for everything associated with all four life streams. At the time of writing, it’s the only tool that I use regularly. Occasionally, I’ll use Midjourney, but not as often as I used to since DALL-E 3 was bundled with my ChatGPT subscription.

Share personal tips on how to make the most of these tools.

Preparing for the Unexpected

This morning’s experience with the impractical creativity time block is just the first of many changes that’ll be made. I’ve just realised that I’ve configured these time blocks to repeat every week until June 30; this would be too optimistic if I weren’t prepared to change and update as needed.

Fantastical, my calendar app of choice makes it easy to change only the current or future time blocks in a single edit. So, I’ll keep them repeating until the end of June, for now.

Say the situation with the contract work changes or an additional short-term contract requires the commitment of every Friday for a month or two, for example. I have to be brutally honest with myself and decide where to make the cuts for the contract duration.

Only the creative or business time block will be revised in this scenario. Personal time should be left unaffected as much as possible. Very occasionally, there may be some impact here, but reducing this to an absolute minimum is important.

Another critical point is to make changes immediately; don’t delay. Make a note or set a reminder. However you do it, keep your planning flexible and always up to date.

A Living Plan, Not a Static Blueprint

I’ll not bore you with an update every week, but I will report back in a month or two. I’m curious how this year is going to pan out. I’m more curious about the coming few months.

Now, I have to get on with it and either make the planning work or adapt it into one that does. No excuses; when you plan something, you must follow through. If that means getting up at 5 AM, go to bed early.

Peter F. Drucker: “Unless commitment is made, there are only promises and hopes, but no plans.

George Bernard Shaw: “Progress is impossible without change, and those who cannot change their minds cannot change anything.”

If you want to have even a chance of succeeding, always be prepared to adapt and refine your strategies continuously.

Final Thoughts

I’m interested in hearing from you, the reader. Add a comment and share your own experiences and plans. Please let us know if you have tips or tricks that help.

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I apologise to my readers for some of the spellings you may feel are incorrect. I was born and brought up in the United Kingdom, and this is the spelling I am comfortable with (Grammarly is happy with it anyway).