Building a side hustle: Tech 101


Hi Bosses!

Steph here. I’m the Founder of Cleveland Flea, and so much has changed on the tech front since I began that business 6 years ago. In fact, when I began Instagram wasn’t even a thing. But one thing hasn’t changed– the stresses and anxiety around tech. One of the first subjects I coach around is the fear of the unknown, and nothing spikes that like the realization of all the new stuff you’ll need to learn to become a small biz in today’s landscape.

We’re on week 4 of our Side Hustle Coaching program and this week, I’m helping our students set up their tech– website, social media, newsletters, payment options, email and task-management apps.

I can’t possibly go into all of it here but I have some advice about figuring out your tech when you’re just starting out.

  1. Don’t panic. Seriously. When you notice you’re panicked about stuff, take a deep breath. Get a pen and paper and write down all the thoughts you’re having that are contributing to your panic. Most times, when you isolate your thoughts you can talk yourself back into a more productive space. Tackle one thing at a time.

  2. You don’t need to be signed up for EVERY app. These days, we really recommend instagram for our creative businesses (especially those who have stuff to sell), Facebook (ads allow you to access so many more people than you can locally), and a blog (if you want conversation you’ve got to start and be a part of that conversation).

  3. You CAN build your own website on Squarespace. BUT you also need good content (photos, writing, your services should be ‘packaged’ in ways that make sense to your customers). Spend the money on a great photographer. And if you can’t write about yourself for the life of you then hire that out, too. Your site will be so much better if there’s good photos and writing.

  4. You will make mistakes, but who cares? Just because you might not be great at everything RIGHT NOW doesn’t mean you shouldn’t try. And fail. It’s part of the deal here.

  5. Use the ‘Toddler Tool’. My friend Shira created this rule for herself because she gets easily overwhelmed by techie issues. She told herself that she only has 2 choices: Do the task at hand or Hand it off. She can’t have a tantrum about it because that doesn’t get it done any quicker (or make her feel like a boss).


Steph Sheldon is founder and Chief Creative Officer of Cleveland Flea Brands. She coaches Dreamers to become Doers (here) and helps Bosses get to $1,000,000 in her own personal coaching business. If you need a creative pep talk, or think you might want to hire her, you can reach her here.

Stephanie Sheldon