These 4 books will help you make better decisions.

Solopreneurs wear many hats. I have been a Solopreneur, on and off, for ten years. I find the ability to decide what I want to spend my time very liberating. At times, however, it can also be very intimidating.

Most companies can distribute decisions through a larger team. When your team is one person, all decisions, good and bad, go through you.

How to spend your time, what you should be working on, whether or not you should be working today; it’s all on you, boss.

By studying these 4 books, I’ve made my business more profitable, practical, and effective. If you apply the principles found in each of them, I’m confident they can help you to also better navigate the forever changing tides of solopreneurship.

Company of One by Paul Jarvis

Why is staying small the next big thing in business?

Paul Jarvis demonstrates in Company of One that running your own business does not have to lead to infinite growth. In fact, he challenges, trying to grow your business beyond ‘enough’ can be detrimental to your overall goals and happiness.

There’s a lot of things that I wasn’t able to articulate about my own business, or my own career, until I read this book. Paul has been around this world for a long time — I think of him as one of the ‘elders’ of the Internet. Having his perspective on what it means to be a Solopreneur is helpful because he provides a valuable framework for how to view your relationship to your audience, to your customers, and to your time.

People who work in traditional businesses have concerns that we don’t have to deal with — overhead, and staff, and management, and hierarchies.

Solopreneurs have none of that, which can be an undeniable advantage. But it also means you don’t have any pushback. If you have something that you’re interested in and that you want to pursue, then you could really screw yourself up.

Chasing the wrong thing is a unique challenge of solopreneurs.

I like how Paul describes opportunities as ‘obligations wearing an appealing mask.’ That’s a really great word of caution for a Company of One, because when we are presented with opportunities, there is not a team of people to provide communal pushback, and to challenge your ideas.

It’s all up to us.

We either make it work, or we don’t.

That daunting challenge is made more bearable by the fact that I can read somebody else’s story, and perspective, and analysis about what this all means, to run your own small business that you’re not trying to scale.

I really like how he talks about his relationship with his audience. He says, if you don’t think about the personality of your business, your audience will assign one to you.

You have the agency (and the responsibility) for declaring your own brand and personality. For example, Paul has this great perspective on rats. He has this great essay on his website about rats, demonstrating how he uses his personality to filter the kinds of people he wants to do business with.

Company of One is a fantastic read, and I really like the companion podcast, where he hosts interviews with many of the case studies from his book. Paul has given a unique and clear perspective on the new gig economy that is proliferating the number of Solopreneurs working for themselves.

Start Finishing by Charlie Gilkey

As a productivity nerd, there are not a lot of people who can teach me things that I don’t already know about productivity and time management, but Charlie Gilkey is one of them.

His practical methods in Start Finishing helped me to re-think my relationship to my time and has given me tools to analyze my projects in new and productive ways. I find his way of unpacking the different layers of a project and prioritizing your calendar, to be very helpful.

After studying this book, I began to examine my time in terms of Focus Blocks and Recovery Blocks. I can’t work much more than 2–3 hours at a time before I burn out. Previous to reading this book, I would just take a short break and get back to focusing — but what has been helpful for me (especially considering my recent debilitating relapse with an autoimmune disorder) is to schedule Recovery Blocks in the middle of my day.

This has helped me preserve the limited endurance that I now have, and it’s helped me get more out of myself. I am a lot more intentional about how I schedule and spend my time, and I often make better choices because of the frameworks he provides.

Beyond the GTD-style tools of productivity, what really makes Charlie’s book special is the ongoing recognition of the different points of failure that can prevent you from finishing what you start.

Charlie doesn’t give you rah-rah platitudes for overcoming challenges; he gives you practical methods to acknowledge these drag points, and to use them to inquire whether or not this is a project worth finishing.

The margins are wide enough for taking good notes, and the design has all the best elements of a practical textbook. From start to finish, this book is a delightful read.

Deep Work by Cal Newport

I have always been a multitasker, and proud of it — until after reading this book. I am surprised to have changed my opinion, but Cal Newport makes a compelling case for unitasking in Deep Work.

I’ve always known about switching cost (the friction of moving from one mindset to another) and how it can decrease your output. When I look at my productivity capacity, though, I’ve always been proud of what I can accomplish while multitasking.

But now I realize, I never fully gave unitasking a proper try.

Cal is an academic, so he doesn’t just posit a theory; he uses case studies and data science to back up his claims. The stories he tells are compelling, and the research behind his ideas is very sound.

The underlying premise is: spending time in Deep Work will allow you to go farther in your chosen field of expertise than Shallow Work.

I see this demonstrated time and time again with my writing. While I am a prolific writer (see my crowded Collected Works page for more) I am not a fantastic writer.

I know that I can produce and publish so much online because I am a good multitasker, and the various mediums of publication (here on Medium, over on LinkedIn, my personal blog, my newsletter) all require a series of technical machinations that I am adept at performing.

Not only can I publish a lot of material, I can also make it look good, in a relatively short period of time.

But this adeptness at the Internet does not translate into particularly high-quality writing. The development of elegant and thorough ideas is done in a state of Deep Work, and not Shallow Work.

After reading this book, I scheduled time in my calendar for writing. Instead of snatching some time when the mood and opportunity presented itself, I became more intentional about entering (and staying in) a state of depth during my writing time.

Especially if you’re a creative entrepreneur, I highly recommend this book. I was surprised at how much it changed my fundamental perception of my work, and my relationship to it.

The Thought Leaders Practice by Matt Church, Peter Cook, and Scott Stein

This is the best business book I read in 2019, and it might be the best book on business I’ve ever read (only time will tell).

The Thought Leaders Practice was written by three Australian business coaches / thought leaders / speakers / trainers — they do it all. Matt ChurchPeter Cook and Scott Stein, help clever people be commercially smart.

The clients that I work with are clever people who aren’t commercially smart yet. (I happen to be one of them.) Although I do a lot of speaking and writing and coaching, I have not been acting nearly as smart as the people who go through their program, Thought Leaders Business School.

They’ve got this great Intellectual Property Snapshot, which is a worksheet where you get a full spectrum on your idea. Working with this process helped me flesh out my own ideas, and identify the weak spots.

For each idea I present to my audience, I can now develop left- and right-brain thinking, I can create Context, Content, and Concept, and I can immediately see if there’s one aspect I am missing. And then, I can deliver it to markets that are willing to pay for it.

I think the biggest thing that has impacted me as a result of reading this book is using the Cluster Strategy to climb the Revenue Ladder.

The Cluster Strategy is a combination of your Message, your Market, and your Method, and those are all interchangeable.

The Revenue Ladder is a series of income levels assigned to colorful belts, like in martial arts.

They say launch a Cluster, a combination of Message and Market and Method, and do this every 90 days. Half of them will succeed and half of them will fail.

If you do this, reliably and regularly, using their templates and models for bringing your ideas to market, and for asking the market what they want to buy.

By doing this, you want to get each Cluster up to $10,000 per month. And if half of them succeed and half fail, then within three years, you’ll have what they call a Black Belt Practice.

With a Black Belt Practice, you’ll be making $60,000 a month, or $720,000, a year. Most people who go through their program who have achieved that level of success are working 50–200 days a year, with one to two support staff. That’s it.

That’s the kind of success that Solopreneurs dream of attaining.

There are a lot of steps I had been skipping, in trying to take this idea to market, and the Thought Leaders Foundation Program helped me identify those skipped steps, and bring my offers to the market in a way that they were most likely to buy.

If you are a Solopreneur who has learned something from one of the 4 book recommendations I’ve given you so far, then trust me when I tell you that this program can transform your life.

Did I miss a good book for Solopreneurs?

Leave a comment if there is a book that has helped you become a better Solopreneur, and if I haven’t read it yet, I’ll make a Book Review on my Youtube channel for it.