ASLU 005: Taking Risks As a Creative Entrepreneur

Episode 5 of the And She Looked Up Podcast wraps up our month long theme of courage. This week we’re tackling a big one: taking risks when you’re a creative entrepreneur.

Risk taking is tricky for most people, regardless of what you do for a living or how you spend your free time. Our brains like things to be safe so they fight us all the way! But when you’re a creative entrepreneur you’re tackling two kinds of risk and they overlap in a lot of ways:

  • business risk: there are so many risks associated with running your own business and a lot of them revolve around finances

  • risk with your art: changing your style, trying a new medium, experimentation

Then there’s also the risk of what happens when you combine the two:

  • if you try a new medium or style, will your existing clients like it and still want to purchase or will you push them away?

  • if you go from writing about food to writing about raising horses or painting watercolours to loom weaving what will happen?

  • when should you go from creative side gig to a full-time small business selling what you create?

  • Should you turn that hobby that gives you a creative outlet and some stress relief into a job?

It can be overwhelming dealing with risk sometimes! But the key thing to remember is you can take a risk without being reckless.

So in this episode (and down below) we’re going to talk about some of the ways you can mitigate those risks and still try new things without putting everything on the line!

Listen to the Episode


How to Navigate The Risks of a Starting or Running Creative Business

  1. Don’t confuse research and procrastination: as we’ve talked about before, procrastination can be a way our brains help us avoid taking risks and sometimes, that can surface as researching something to death. But at the same time, doing your research is an important preparation tool for tackling something new. Researching a topic can give you valuable insight into what’s involved from a time, supplies and financial standpoint so don’t skip this step!

  2. Nobody needs to know what you’re thinking: just because you’re pondering a new idea doesn’t mean you need to tell the whole world… yet. Do a little research quietly and if your new idea or project looks like it has some merit, then you can start talking to others about it.

  3. It can be equally risky to stay in your day job as it is to go out on your own: sometimes the “security” of a “real” job can be an illusion. All industries and sectors can experience ups and downs. Layoffs can come out of nowhere. Your safe job could disappear overnight and not being prepared for that can be just as risky as taking smart steps to start your own business.

  4.  Diversification: It’s great to have one really successful revenue stream. But what if something happens to disrupt that? Do you have other revenue sources that can pick up the slack? Always keep your eyes open for how you can diversify your business and mitigate the risk of having all your eggs in one basket

  5. Offer different points of entry to your customers. You might sell a greeting card made from one of your pieces of art for $4 but the original piece might sell for $100s of dollars. If you’re a digital content creator you might give away a lot of content for free on your website (that’s monetized by ads) but then sell an ebook that costs $10 or a group course that sells for $300 or one on one classes that sell for $1000.

How To Mitigate The Risk of Quitting Your Day Job

  1. Do everything you can to pay off your consumer debt before you quit. Having less payments to worry about each month will give you additional piece of mind.

  2. Start saving money so you have a cushion in the bank to help you get through the rough start-up months and the inevitable slow downs most creative businesses see during the summer. How much money will depend on your level or risk tolerance but we’d suggest a minimum of 3 months of living expenses. Most people are comfortable with 6 months. If you’re very worried about debt or borrowing, you might need a year.

  3. Learn to live on less before you quit your job. You likely won’t make your usual income for anywhere from six months to a year (maybe a lot longer depending on your situation). By socking away any extra money into a savings or investment account while you have the earning ability, you’ll give yourself a taste of what it’s like to live with less money. Melissa read The Wealthy Barber back when she was 20 and it set her up for having a nice nest egg set aside when she quit her job 17 years later!

  4. Make large purchases prior to quitting your day job. It could be specific supplies, equipment (camera gear, computers, high quality scanners or printers, etc) to business cards or a website or logo design. Spend the money when you know you have a paycheque still coming in the next month.

  5. Read, read, read. There are so many books out there on how to prep for quitting your job - we list some of our favourites in the Resource section at the bottom of this article.

  6. Talk to others who have quit their jobs. Don’t just talk to people like you. You don’t know what your future holds and what may be your norm today could be completely different a year or two from now. Talk to people who’ve just started out on their own, talk to people who’ve been doing this for 10 years or 20 years. Talk to people who have kids and those who don’t have kids. Talk to people in big cities (where competition can be high) to people living in small towns (where there’s more community support). Talk to people who work in their homes and people who have dedicated office or studio space. Talk to people who sell products and those who sell services - or who do both! Talk to people who have spouses or partners who work from home or who earn the bigger income - or the smaller income.

  7. Do some work on the side (if your employment contract allows it). Start small while you’re still working full time. It’s a good way to gauge interest and your ability to work on your own.

  8. Leap. No matter how much you prepare, at some point you have to make the leap. Just like nobody is ever completely ready to have kids, nobody is every completely ready to quit their job. But that doesn’t mean it’s not the right time or that you can’t do this.

Managing Creative Risk

There are times where the risks we take are more directly related to our art. Should we try something new? Should we take our style in a different direction? Should we sell our work? Will our clients and audiences embrace your new found growth or experimentation? Should you market it separately from your current work?

These are all big questions all working creatives struggle with from time to time.

Think Carefully Before You Monetize all of Your Work

Creating as a hobby is very different from being a working creative. Working creatives have to summon creativity on demand - even when they’re not feeling it.

Creating as a hobby means you can do it 100% on your own terms: when you feel like it, how you feel like it and with whatever materials you feel like using.

It can be tempting to monetize every aspect of your work - especially if your audience is encouraging you to monetize something. But there’s a risk in that - once you monetize it, that thing that brought you great joy, becomes a job. You might, and hopefully will, continue to enjoy it or you might find that the business aspects of it take away from your enjoyment. Usually it’s a combination of both. So try to keep something back that’s just for you - for pure enjoyment. We need hobbies for relaxation and mental health. They don’t all need to earn us a living.

If you do want to try putting your work out there but you’re not sure how it will be received, start small:

  1. Open an Etsy shop - you can sell your items in small quantities without committing to building your own website or even social media channels while still getting a sense of the logistics or selling your product: pricing, packaging, shipping, customer service

  2. If you already have a lot of end results from your hobby - be they painted canvases, photographs, hand carved wooden boxes - look for opportunities to sell them with no risk. Try a local café with art on the walls or a small local craft market - especially during the holiday season. You’ve already got the inventory so why not give it a go and get some experience under your belt with little investment.

  3. Start a blog - this is a great way to share your hobby with the world. (hello writers!) and to see what kind of response you get.

  4. Leverage your local community: this is a great grassroots way to grow an audience or following. Show up at craft fairs and markets, look out for calls for submissions, teach classes at night school or community centres, check out community facebook groups.

  5. Tell your friends! Friends can be a great support system (and customers) and they can start the word of mouth.

All of these suggestions will also get you thinking about the business side of creating: marketing, finances, showing up every day…

Heading in a New Creative Direction?

If you have a loyal audience and market for your work, heading in a new direction can be scary. Will they like what you’re creating? What if they hate it? Here’s some ways you can mitigate your risk:

  • test the waters through social media - temporary posts like Instagram Stories or Snapchat are a good way to put new content out without putting it in your main feeds

  • if the response is favourable try branding your new style under a different name with its own channels and website or Etsy shop.

  • consider this a way to diversify your income. All businesses should think of different revenue streams to ensure they have a healthy business. A new creative direction can be an opportunity to do just that.

The Risk of Success

So often when we worry about all the things that can go wrong when we take a risk. But don’t forget to consider what can happen if you succeed? Because a lot of people DO succeed!

Are you prepared to scale up if your creative business is a success? Will you be able to meet demand? How will you manage pricing? Will you hire help?

These are good problems to have but… they are still problems you’ll have to solve. Make sure you run through those scenarios as well when you think about the risks or starting or trying something new!

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