Back to school: entering Solo Academy

5 min read
Matthew Pattinson

So you have launched your side hustle. You have put in the hours to turn your moonshot idea into the beginnings of a reality. Maybe your passion is even turning a profit.

Of course, the thing you need to do now is buckle down to keep your side hustle ticking along. Nobody would argue with you on that.

But there’s one other thing you mustn’t overlook at this early stage of its development, and that’s the power of learning.

With September comes back to school, and it’s not just for the kids. Now is the time to start expanding your knowledge base.


Sometimes it’s good to go back to basics. It may be a technology as old as the hills, but books - whether in paper or digital form - serve an enduring purpose: to introduce us to things we don’t know and to give us perspectives that we can bring to bear on our everyday life and work.

Reading books gives us direct access to some of the sharpest, most experienced minds on the planet, living and departed.

Think strategy books like The Art of War that teach business principles from a martial arts perspective or 20th century classics like Dale Carnegie’s How to Win Friends and Influence People.

If this is too old school, skew modern. Read Enterprise Nation Emma Jones’ ‘Working 5 to 9: How to Start a Successful Business in Your Spare Time’ or explore Chris Guillebeau’s ‘Side Hustle: From Idea to Income in 27 Days’. See what side-hustler-in-chief Nick Loper is musing on. Pick up a book on something you heard at the watercooler, on a podcast, or from an old college friend but never got round to reading. Why wouldn’t you want to know what the best minds think?

Sure, you will still want to read articles online. The internet is awash with resources to help you learn new skills and gain insights from the people you admire.

But tread carefully. The challenge with internet articles is the constant temptation to check email or Facebook, watch videos, or click a link and leave the page.

So make time for deeper reading. Carry a book when you’re out and about, and instead of reaching for your smartphone when the urge takes you, crack it open and pick up where you left off. You’ll be amazed at how much reading you can get done in those down moments.

If the physical act of reading is not for you, try podcasts or audiobooks. Let your ears do the reading instead of your eyes.

Turning your side hustle into a page turner

Support the development of your side hustle through reading. Of all the investments a solopreneur can make, books may yield the highest return on investment.

“The hallmark of the most successful people is that they read”, said US president Harry Truman. “Not all readers are leaders, but all leaders are readers”.


Books are a great resource, but books are written by people. If you really want to take your learning into the real world, talk to the people around you. As a side hustler looking to spread your wings, embrace the art of conversation.

Practice striking up conversations in public. Lean into things you don’t know. Be curious, ask questions, and listen. You don’t know what you might find out.

Go further. Dig out online resources and web communities that can help answer questions and guide you along the way.

And remember that simply talking about your business is often the best way of getting the word out: the original word-of-mouth marketing. The number of business opportunities that arose out of chance conversations is uncountable. Serendipity is everywhere if you are open to it.


Rewrite your side hustle through self education

So you’re reading and you’re talking. The next step along the side hustler’s journey is practice, testing out what you know.

You might think that the best way to practice is by doing: make a difficult phone call, learn a new online system, understand how to replace a piece of technology. It’s true that doing is practice, and practice is learning.

But there is one other thing that you should be doing to cement all your new knowledge, and that is to write.

Writing is the perfect litmus test for what you know. It helps straighten out ideas, identify gaps, and discover your voice.

If writing is hard, writing about new things is even harder. But doing difficult things with determination is generally the best possible way of making hard things easy over time.

Don’t make it difficult getting started. Write about things relevant to your fledgling enterprise. Write landing pages or marketing flyers that advance your business. Write blog posts that can go on your website.

But also write things that are just for you. Experiment with your thoughts and ideas. Identify gaps in your knowledge base, and go back and fill them in.

Welcome to Solo Academy

Congratulations, you’re in! You’ve been reading, speaking, and writing. You’ve been thinking, tinkering, testing, and probing. And you’ve been working hard to keep your side hustle moving forward at the same time.

And while what you learned in the first month will set the foundation for your future business, what you have accomplished in month two will begin to change the way you think and feel as a person. You are becoming a solopreneur.

It takes a village to fly solo. The more you stay open to learning, the more you will enjoy the support of a community hungry for success.

The trick is to keep motivated and to remain curious. Identify those areas of expertise relevant to your field of work and always be learning.