In March this year, The Song Foundry Inc., the business behind the site, turned five. And to celebrate five years of running a real grownup company, I’d planned an article about some of the things I’d learned in that time.

But then (spoiler alert) the world went a bit crazy. Other things seemed more important and this article got put to one side. 

Still, nine months later, and just before 2020 ends, it felt like an article worth sharing. So if you’re thinking about building a business around what you create, here are nine real-life lessons I learned as a creative entrepreneur that ought to help you out too. 


Lesson #1: It’s a Long Game

Chairman Mao might not have been right about everything, but he was really onto something with all those five-year plans.

Building a business is a long game. That’s true whether your business is selling ring binders, legal advice or songs. 

As a creative entrepreneur, it takes time to build a catalog of work to share. It takes time for people to get to know you and what you do. It takes time for you to figure out exactly who your business is for, what you can do for them and how you can get what you’ve created in front of them.

Author Ta-Nehisi Coates wasn’t lying when he said “If you can stick out the first ten years, you’ll be OK”. He was talking about being an author, but he could have meant it for any creative field.

The good news is that, as an artist, while a creative career usually takes years and years to build, a patiently-built career is more likely to last. And if making art for a living is the thing you want to do with your life, it’s going to be tough, but it will be worth it. You’ve just got to give it time. Lots of time.

Every year for the past five years The Song Foundry has grown. I’ve gone from 150 site visitors a month to over 25,000 site visitors a month. I’ve gone from making fifty or sixty dollars in book royalties each month to making thousands of dollars each month. And I’ve gone from a nice email or weird YouTube comment every few months to enough of those to keep me happy that I’m doing something right. 

Nine Lessons as a Creative Entrepreneur - Wall Quotation
Most entrepreneurs underestimate both the time it takes to get established and how exciting things can get once you are. Read that again.

And as I build a bigger and bigger body of work, I give more people more ways to find me, and those people start to explore the other things I’ve made, and those people start to talk about me to other people, and then those other people become more easily impressed by what I do because if people are talking about what I do it must be good, right? And that’s how 99% of creative careers grow – step by step, not overnight success. Don’t let anyone tell you otherwise.


Lesson #2: Don’t Wait: Do

One of the biggest lessons I learnt running a business – and especially as a solo entrepreneur – is that if you don’t make it happen, it probably won’t.

The good news is that the Internet has changed everything for creative entrepreneurs. The only way to succeed isn’t just to wait around until the right gatekeeper opens the right door (or gate, I guess) to success. No. Instead, you get to make yourself a success – on whatever terms you want. Being an artist is so Twentieth Century. In the age of the Internet, being a creative entrepreneur – creating your own opportunities and platform to showcase what you do – is how it works.

And as you find out, it’s almost always better to do the ‘wrong’ thing than do nothing. That’s how you discover what the ‘right’ thing is.

So even though you’re unsure, even though you probably feel like you have no idea what you’re doing, the best thing you can do is start. Because if you don’t personally make it happen, chances are it won’t.


Lesson #3: Businesses Are About Relationships

Sure, on the surface every business is about a specific product or service. You do or make a thing that you put out into the world, and that’s your business.

But it’s only a business because there are people out there who want that thing. It’s only a business because you, as a human being, created something that other human beings want to be a part of.

In other words, businesses aren’t really about things – they’re about people.

I’ve sat through enough dodgy marketing webinars and read enough questionable marketing books that focus on quick tricks designed to get people to part with their money. But to me that’s backwards – the goal of a good creative business is to make people genuinely want what you’re selling, or want to support what you’re making, or want to stay in touch with you to see what you do next.

Building businesses is about building relationships. It’s not just what you do, but who you do it for. It’s not just the product, but the community you build around it – and how you make their life better than it would be if you weren’t in it.

A lot of people go into any business assuming it’s about making the best product or service possible. But don’t underestimate your role as a connector – someone who brings people together. Those people are the real heroes.


Lesson #4: Every Business Is Different – So You’ll Only Discover How to Build Yours by Trying Things

You might know the Silicon Valley mantra ‘Fail fast, fail early’. It’s a nifty way of saying every new business idea has a teething period where lots of things will go wrong before you can learn how to do them right. That’s Lesson #2 – why doing the ‘wrong’ thing is always better than doing nothing. And it’s true to pretty much every business, in California or otherwise.

You’ll learn a lot from studying the businesses and careers of people you admire. You’ll grow a lot from imitating your heroes. But you’ll almost never succeed by copying them exactly.

You aren’t those people. Your business idea is not their business idea. Your circumstances, your audience, your platform is not their platform. And you have to figure everything out your way on your terms. And the only way to do that is to try a bunch of shit and see what works.

By all means read every book about Warren Buffett or Steve Jobs or Oprah Winfrey that you like. But those books will only give you blueprints for success, not a formula. You have to get your hands dirty and learn first-hand what works – and doesn’t – for you. (Again, see Lesson #2.)

There’s another famous saying that history doesn’t repeat itself, but it does rhyme. And that’s true in business too.

Nine Lessons as a Creative Entrepreneur - Computer Code
Running a creative business doesn’t come with instructions. You have to write your own.

Lesson #5: Luck Is Always a Factor

One of the dangers of school and college – especially for people who flourish in school and college – is that you pick up this neat idea that hard work equals success. And if you only work harder, you’ll see better results.

It’s a nice idea. But the real world doesn’t always work like that.

Don’t get me wrong – success almost never comes without hard work.

But the opposite isn’t always true – hard work, at least in the real world, doesn’t guarantee success.

I’ve pored my heart, and plenty of hours, into content for this site that barely got any attention. Meanwhile, the most popular post on the site – by far – took me a two-hour train ride to write. And that’s how it works in general.

You can only control what you make. You can’t really control how it’s received. That’s more down to trends and tastes and algorithms and right-place-right time luck than anything else.

Remember earlier this year when Billie Eilish hilariously apologized for her success at the Grammy’s because she thought she didn’t deserve it more than anyone else? I love Billie Eilish, but damn, she’s got a point. She’s great, but so are plenty of other people who don’t see anything like that level of recognition.

The trouble, of course, is that it’s human nature to assume that when we’re successful, it’s down to hard work, while when we’re not, it’s just (bad) luck. The truth is – at least in any creative field – luck is always a factor.

Sure, it’s up to you to create your own luck. And sure, there’s an art to capitalizing on your lucky breaks. But there’s no way to control luck completely – that’s kind of the definition of how luck works.

Sometimes all you can do is create your best work, try to get it in front of as many people as you can, and realize that everything beyond that is out of your control.


Lesson #6: Being an Entrepreneur Brings Some Freedom, But Not as Much as Most People Think

I have a pretty awesome life. Through some combination of luck and choice, I’ve not worked anything even close to a 9-to-5 since 2010. And now, I’m not sure I could ever work that kind of ‘normal’ job again.

I have a lot of freedom to travel, for work and fun. In 2017 I took three weeks off to go visit ten different European countries. In 2018 I spent over a month in Costa Rica. And in January this year I booked a last-minute trip to Lisbon to spend ten days working on my new book.

That’s an insane level of freedom. But it comes at a price.

In the eternal words of that song from Team America, freedom isn’t free.

Nine Lessons as a Creative Entrepreneur - Standing on a beach at sunset

Balancing running a creative business and my career as a theatre songwriter is a lot of responsibility. There’s no HR department, no payroll, no marketing department. There’s just me. I have to juggle all of that.

And as much as people imagine being an entrepreneur brings the ultimate level of freedom – planted in a lot of people’s minds by the ‘lifestyle design’ movement, including books like Tim Ferriss’s The Four-Hour Workweek – that’s not how it works in reality.

OK, I don’t have a boss to report to. But it doesn’t mean I get to swan around doing whatever I want, whenever I want. I have a community to build things for – see Lesson #3. When I work with other people, I have things to do for them so they can do their jobs. I have paperwork I have to do to keep the IRS and New York State happy. I have to work to deadlines – even if I choose them – to make sure everything gets done on time.

And on top of that, I have to balance all of the needs of the business – creative and financial (more on that in Lesson #7) – all while being responsible for the overall vision and direction of where I think the company should go.

That’s true for any business: being your own boss comes with some freedom, but also a different set of responsibilities and restrictions than you get working for someone else, in one place, with regular hours.

And is it worth it? For me, yes. But it’s no walk in the park and definitely not for everyone.

Building any kind of business is a commitment (see Lesson #1) that means sacrificing some things in order to get other things. That’s the unsexy truth that that free dropping webinar that keeps popping up in your Facebook ads won’t tell you, but it’s how it works. Listen to the marionettes: freedom isn’t free.


Lesson #7: Balancing Art and Commerce Is Tedious

You don’t need to be Bernie Sanders to agree with this, but late capitalism sucks. A tiny handful of people has far too much money and power. Opportunity should be spread out better. Nobody in an advanced economy should have to work multiple jobs just to stay alive.

And that’s the reality of being alive right now. In some ways, it’s the best time there’s ever been for doing something creative with your life. But it’s also a difficult time to make a living from what you create.

All the misconceptions about what it’s like to be a ‘struggling artist’ aside, making a living doing something creative is tough. Making a living doing something most people is important is tough. (Yes, school teachers and social workers should be paid more than investment bankers.)

Surviving as a creative entrepreneur in a capitalist society is tough and often tedious. I have plenty of flashy credits to my name – I’m a bestselling author, I co-wrote a significant regional stage show, I signed a promising film deal before I turned 30 – and even with all those things it’s not been that long since I was getting by on $500 some months.

To be clear, I do not care about money. I’m not doing this to make money. I’m just trying to create the things that matter – at least, to me – while making enough to live a comfortable life. And, as I’ve learned, sometimes the thing you’ve done that sounds flashy isn’t the thing that helps you make a living, and vice versa.

I guess that’s just Lesson #5 reworded – life isn’t fair. And sometimes all you can do is accept it and learn to do your best within it.

Nine Lessons as a Creative Entrepreneur | International Banknotes | The Song Foundry
Putting a load of international banknotes together like this might look creative and artistic. But for most artists, dealing with the financial side of running a creative business is boring but important.

Surviving as an artist means balancing creating the things that are important with doing the things that will earn you a living. Sometimes they’re the same thing, but usually they’re not.

And while surviving in itself is a good thing – that probably goes without saying – it’s also a good thing creatively too: it means you get to go on and create the next thing, and the thing after that.

It’s hard for most artists to have a healthy relationship with money. For all your passion, drive and creativity, the thing that makes sense financially is often the thing that wins out in the end. For your creative business to keep existing, it has to make sense financially. For all the true value of a creative project, you can’t spend your life only making things for free or making things at a financial loss. It’s not sustainable. (Congrats, capitalism. I hope you’re happy.)

But on the plus side, there are always ways to balance doing the things that make your soul sing with the things that keep your bills paid. And part of the fun of being a creative entrepreneur is finding them.

OK. Maybe it’s not as fun as it sounds, but it’s part of the game all the same. You learn to embrace that.


Lesson #8: As an Entrepreneur, You’re Always Growing. That Can Be Tough. But It’s Necessary.

One of the most stimulating parts of being a creative entrepreneur is that you’re never standing still. You’re always growing. Your business is always becoming something slightly different. You’re always facing some new challenge or new opportunity.

Yes, that’s creatively stimulating, and sometimes thrilling. But it’s also tough.

Just over five years ago I was working hard to get my business established and facing the reality of the responsibilities that come with that. I slept a lot that month. Just the thought of taking that big step was pretty overwhelming. All the ‘Am I ready for this?’ or even ‘Am I up to this?’ was a lot to process. I had to give myself the time and space to let that happen.

And, honestly, that feeling of not being able to touch the bottom has come back with every major new milestone in my career.

Now, of course, things are much easier. I understand the day-to-day of what I do much better. I’m much quicker at it. It doesn’t psych me out the way it did one time. At least, until I decide to take some other big, bold step forward and that growth process happens over again.

And that’s how the life cycle of any business works. It’s another reason businesses take time (Lesson #1). And because the only way to run yours is to figure it out first-hand (Lesson #4), you have to accept that difficult growth is part of what you signed up for as a creative entrepreneur.

Still, the best lessons are often the toughest lessons. You can’t grow if you’re comfortable all the time. And if you wanted to be comfortable all the time, you probably don’t want to be an entrepreneur in the first place.


Lesson #9: You Will Figure It Out

If one of the biggest questions that kept me away when I started out was ‘Am I up to this?’, I now know the answer: ‘no’.

Or, more specifically, ‘no, not yet’.

Because that’s the truth about running a creative business – nobody really knows what they’re doing when they start out. And even later on in the business’s lifespan, a lot of people you think are nailing it are just winging it convincingly.

I don’t say that to criticize anyone, or undermine my own skills or success, it’s just the truth – if your business is doing something you have to figure out first-hand (Lesson #4) and you’re always going to be challenged by new things (Lesson #8), you’re not going to have the perfect answer, every time. You’re just going to use your best judgment (Lesson #2) and, if necessary, try to be a bit better next time.

Nine Lessons as a Creative Entrepreneur - Star Wars Stormtrooper punching a lightbulb
This guy might work for an evil, authoritarian empire, but he believes in you, champ.

But that’s part of the thrill of doing something creative. That’s why entrepreneurs love being entrepreneurs – they like the not knowing. They like solving problems they’ve never done before. They like doing things they’ve never exactly done before.

And sure, it makes sense to start a business in an area you already have some experience. But anyone who thinks they’ve got it all figured out is either bullshitting you, bullshitting themselves or – most likely – bullshitting everyone around them.

Instead, smart creative entrepreneurs learn that they will figure it out. They’ll find out what they need to know. They’ll ask someone. They’ll hire someone. They’ll make mistakes but trust they’ll figure it out in the end.

And 95% of the time, that’s the only secret – if you can call it a secret – to success in business and art: perseverance. It’s just keeping going.

All of the clichés are true. Success is a messy, squiggly line not a straight, simple one. A lot of people who give up didn’t realize how close they were to success when they do. Failure is the only route to success.

It’s not a question of if you have what it takes. It’s a question of whether you’re willing to hang on long enough to learn to have what it takes. And that’s the litmus test of whether a business idea is worth sticking with or not – are you still excited about what you’re building?

If the business is thriving, that’s often an easy ‘yes’. If it isn’t yet, things get a bit trickier.

Businesses are hard. Despite what it might look like, I still think about giving up. I still think about finding a regular job and taking on much less responsibility and having a much more normal life. At least, I do for about eight seconds before I remember that’s not what I really want. And as long as my answer is ‘Nah, keep at it’, I’ll be here. And I’ll keep learning. And I’ll keep growing.

And ultimately, if you’re prepared to hold on long enough too, you’ll find a way to make it work. Maybe not the way you expected when you started out. Maybe not the way you hoped when you started out. But maybe some way you can be equally as proud of.

So if you’re sitting on a creative or entrepreneurial idea, your most important question isn’t ‘Will this idea work?’ but ‘Do I want to spend my life trying out new ideas?’. And if you are willing to spend your life trying to find ways to make your ideas or your art viable, then congratulations, you’re a creative entrepreneur.

And that’s true whether you feel like you know what you’re doing or not. Because either you do know what you’re doing – even if you don’t know it yet – or you will – even if you don’t know it yet.


Header image by Riccardo Annandale on Unsplash.