I recently looked in my 2016 planner (good thing I never throw these things awaaaaay) and found a diagram I’d drawn at the very beginning of my freelance journey.

[image description: A grid with two rows and two columns. The columns are labeled “low risk” and “high risk” and the rows are labeled “low reward” and “high reward.”]

When I drew this diagram, I was a new parent and had recently decided not to return to my teaching job that school year. I was trying to figure out what to do to earn some money and combat some of the exhausting boredom that comes with taking care of a semi-sentient potato 24/7. (I love my child, I really do, but that is essentially what they were for the first 6 months of life.)

I’m blessed (or cursed, depending on my mood that day) with a large array of skills and interests. With a demanding potato to care for, I had to prioritize what to do with my remaining time and energy. 

I used two criteria to evaluate my options:

  • Risk of rejection, failure, or running out of work
  • Reward potential, both financial and fulfillingness

Some options, like teaching online or blogging, carried very low risk. VIPKid was serving me recruitment ads every day. I’d already been blogging for years. But the reward for these was relatively low. I’d never actually made any money from blogging, and while teaching online paid okay, there was also a lot more work involved.

On the other end were the Big Dreams: earning a living from writing or coaching. The risk for failure and rejection were quite high, but so were the rewards: the fulfillment of doing creative work and helping others do the same, the flexible schedule, and no limits on my earning potential.

I was able to get from the low risk, low reward box to the high risk, high reward box within about a year. The key to that was going through the third box: low risk, high reward.

A mutual friend introduced me to a professional freelance marketer who needed help with some projects. By working with them, I was able to learn the ropes of project management, client interaction, marketing strategy, web design, and just the running of a business, in a low risk environment. I didn’t have to worry about botching a sales call and losing a project, and I knew I could call in backup if I coded myself into a corner. It was a huge confidence booster. Eventually, this mentor handed off a client, who became my first recurring contract and provided much-needed income stability while I got started on that high risk, high reward box.   

When you start your creative business, it’s easy to have eyes only for the high risk, high reward box. The brick and mortar shop, the full-service team, the dedicated studio, the book deal. And that vision is absolutely essential, so hold onto that. 

It’s also easy to let fear keep you in the low risk, low reward box: keeping your work hidden, downplaying your skills for fear of overpromising, not asking for referrals or bidding on projects because you don’t feel quite good enough. (I GUARANTEE that mediocre white men do not do any of these things, so stop it!)

That low risk, high reward zone is a great way to transition from fear to realizing your dreams. You get to practice taking risks when the stakes are low, and you can build up your resources for taking bigger risks. Even though I’ve been in the high risk, high reward space for several years now, I still keep at least 20% of my time for one of my corporate clients. The articles I write for them aren’t going to win me any Pulitzers, but I usually net about $300/hour on one of their projects, which subsidizes other work that’s more fulfilling but less lucrative.

Think, Feel, Do

  1. Draw a grid of risk vs. reward for your creative work. Start by filling in the high risk, high reward box. What are your big dreams? Then work backward to fill in lower risk but still rewarding ways to gain the experience you need, save up money, or build an audience for your high risk, high reward ventures.
  2. Imagine working on these lower risk, high reward tasks for six months or a year. How does that make you feel? (It’s normal to feel like we either don’t deserve to be rewarded for low risk work, or that only big risks are worth taking. I just challenge you to question those feelings if that’s where you are.)
  3. Pick a small risk to take this week that could lead to something rewarding: a conversation with someone who might know potential clients, a post about your work, an invitation to collaborate. Put it on your calendar, and do it!

Let me know how it goes!


Auntie JDF