Stealing Second Base: From Side Gig to Self Employed Full Time

by Katherine

Welcome to #DifferentLifeStories, where Without Boxes is sharing how people are living differently right now in the real world.

Enter Katherine Stimson:

“You can’t steal second base with one foot still on first.”

Katherine Stimson

In the spring of 2010, a Facebook ad posted by a total stranger caught my attention: Dallas Artist Mastermind Group at Buzzbrews Kitchen. Led by Dallas/Los Angeles photographer Michael Jackson, the mastermind group of artists, photographers, musicians, playwrights, etc. met weekly that spring. We shared ideas for marketing, branding, and self promotion, and, more importantly, how to get out of the “9-5 day job” pace of life. How could we (and I) earn a full-time income from our chosen art or arts-related career, on our own terms? What would that life look like?

One week, PR/marketing guru Jeff Crilley joined the group as a guest speaker. He told us about his journey from a full-time gig anchoring TV news; to anchoring TV news, writing a book, and juggling book promotion; to walking away from the TV news world to found his own PR firm. One sentence of the evening stuck with me:

You can’t steal second base with one foot still on first.

Literally: WHAT is the point you decide to take a risk, get both feet fully off first base, in order to get to the next phase of your life?

In my case, something happened in my mid-twenties (and to many of my friends). I was comfortable, complacent, and I had stopped truly experiencing life: Trying new things, having new experiences, going outside of my comfort zone. I had stopped taking risks.

I had equated quality of life with a successful career and financial stability.

With self-employment, I was determined to seize opportunities to try something new at every chance I could.

So how did I do it? A challenge! Michael of the Artist Mastermind Group challenged us to come up with a 30-day plan: In 30 days, how could you change your life to live the life you’ve always wanted to have? I took on the challenge, and later that summer, I was no longer working the “9-5 day job.”

I had made the leap from first to second base.

Kat Stimson leaping to second base

How can YOU do it?

Take a risk, but make it a calculated risk.

With Michael’s challenge, I assembled a “tool box” of what I would need to “steal second base:”

  • Client list already in place: Start with one client, but then add another.The more sources of diverse income you can have, the better. You want to have several clients already secured before “making the leap!”

  • Humility and nothing is above you! I suggest having some “side gigs” you can do while income is dry. They may not be glamorous or anything related to what you want to do, but should get you cash when you need it. Ideally, these would be “quick and easy” work with a flexible or on demand schedule so the side gigs don’t consume your time. I recommend bartending and brand ambassador work. For me, I bartended wine promotions for a few years until I had steady income from my freelancing. I was able to make $15-$20/hour doing it, set my own schedule… and learned lots about wine!

  • Marketing plan: Develop a marketing plan specific for your business. Identify your niche: What are you offering that no one else is? What sets you apart? For example, I specialize in entertainment production for marathons. It’s a niche market, with multiple repeat clients that pay regularly. You want to offer something unique and valuable that one else is…and that clients will keep coming back for.

  • Website: Your “calling card” to current and potential clients. I’m a fan of SquareSpace for a professional looking DIY website for a low hosting cost per month.

  • Human capital and “Call in the Troops”: Join the (it’s free). It’s a great networking opportunity online and offline with fellow freelancers. They also offer opportunities for group health insurance, long-term disability insurance, legal advice, and financial/tax advice.

  • Get out of your comfort zone – and I don’t mean in work.

Kat Stimson with rockets

Go jump out of a perfectly good airplane, go zip-lining, take a solo road trip cross country and Couchsurf. Do something to get out of your comfort zone…as a freelancer you’ll need to be doing lots of it. And your next business partner may come from where you least expect it, such as random stranger you hosted in your guest room from

Here’s what you should get out there and learn:

  • Public speaking skills: Join a local club to improve public speaking skills. In addition to practicing prepared and impromptu speaking and talking about your business, it’s a great networking opportunity/possible source for new clients.

  • How to make an invoice, a contract, and W9: Have a basic contract, invoice, and completed W9 ready to email out to any client on demand. Don’t assume they have a contract ready to send you, because most won’t. And “he who speaks first” gets the best deal. By leading off negotiations with your own contract first, its much easier to modify your own document than a bunch of legalese that’s handed to you and hard to understand!

  • Safety Net: Six months of savings in the bank before quitting the day job is ideal. Or, back to having those “side gigs” lined up!

  • Reassess your financial means and live within your means: I may drive a used Honda, live in a modest apartment, and have no shame about dumpster diving. Find everything that’s low cost/free to do in town, take a picnic & BYOB.

  • Passion: Four years later, and at the risk of sounding cliché, I can honestly say I wake up every day excited to “go to work” and grateful for the life I’m fortunate to have. Some days “work” may be at home in Dallas, on the road in the middle of a spontaneous road trip to visit friends, or at a marathon in Hawaii at 4am. Or, I may take a day off on a Wednesday to go to the beach or study dance. If you’re not passionate about what you’re about to embark on, don’t do it.

  • …And a deadline: 30 days, two months, six months? I truly believe nothing gets done without a deadline in mind. I challenge YOU to “assemble the toolbox” and to set the deadline of when your “9 to 5” ends and freelancing begins.

“You can’t steal second base with one foot still on first.”

About Katherine

How do we know Katherine knows what she’s talking about? Well, just take a look at her resume. It’s pretty impressive what she’s been able to do using these same exact tips.

Katherine Stimson with friends

Katherine Stimson, CSEP

Katherine Stimson, CSEP, is an entertainment and event professional based in Dallas/Fort Worth, Texas. Her work experience includes coordinating entertainment and talent for the cruise industry, corporate, social events, and experiential marketing campaigns.

Through her company, K Stimson Events, LLC, she works as a freelance live entertainment producer. Her clients include: Continental Event and Sports Management Group, LLC, the producers of the award-winning Divas Half Marathon series (Honolulu, Puerto Rico, San Francisco, Long Island, North Myrtle Beach, Branson, Peachtree City, DC Wine Country, and Galveston), and the NC Half Marathon and Myrtle Beach Mini Marathon; Life Time Fitness Athletic Events (the producers of the Miami Marathon, Publix Georgia Marathon, Chicago Half Marathon, First Watch Sarasota Half Marathon, New Jersey Marathon, and the Michelob Ultra 13.1 Marathon series.

She received the Certified Special Events Professional (CSEP) designation from the International Special Events Society (ISES) in 2014. She is also an Adjunct Instructor in the Travel, Exposition and Meeting Management Program at Richland College in Dallas.

Image credits: Kai Oberhäuser, Katherine Stimson by Ivan Palacios

First published June 27, 2016

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