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How I quit my job and launched my dream business (without going over a cliff)

Last year, I finally did it: I left my employer of 20+ years (!) and became a solo business owner.

The dream of self-employment goes back many years for me, but when my friend Janet sent me this article by copywriter (and my hero to this day) Laura Belgray, I was like wait, what?

I could be myself and make amazing money WRITING? On my terms? Eating overpriced raspberries from the couch?!

I truly never thought that I could be a writer in any other context outside of “for fun.”

Still, it took me another 4+ years to pull the trigger and actually quit my job.

What finally got me over the line?

Baby steps.

If you’re inspired to start a copywriting business, or any business (or launch any dream really): consider taking these seven baby steps while you’re still employed.

1. Buy a bunch of adorable notebooks.

Photo by pure julia on Unsplash

My first assignment from my (amazing) coach, Courtney Pinkerton, was to buy some notebooks and set up an organized way to collect ideas for my new business.

I remember driving over to this sweet little century-old vintage stationery shop on a sunny and cold winter day, proclaiming to the cashier that I was starting a business.

I felt sparkly and energized…and also like a huge imposter. The words felt bizarre coming out of my mouth.

“I’m starting a business!”

(All the demons: “What the heck do you know about starting a business??? You are so never doing this!”)

The cashier congratulated me heartily and I went home and started writing ideas in my notebooks, demons be damned.

Looking back, it’s totally wild how fully-formed my ideas were, even back then.

Trust those. They’re absolute gold.

2. Listen to ALL the podcasts.

Somewhere around this time, my friend Laura (not Belgray), a self-employed designer/entrepreneurial legend and early inspiration of mine, sent me a design podcast to listen to: designers talking about how to work with copywriters.

I devoured it. It felt like a window into my future.

I realized I could search in my podcast app for “copywriting” and, lo and behold, I found the Hot Copy podcast. Enter Belinda Weaver and Kate Toon, two humans with oodles of experience sharing massive amounts of wisdom every two weeks for like 5 years.

Me, at the gym in 2019, getting fired up about my future while listening to copywriter podcasts.

I listened at the gym, letting myself be carried away by my future work fantasy. I went deep into the archives.

The more I listened and absorbed the real-life experiences of these smart and hilarious and encouraging women, the more I knew I could do this.

Podcasts are another goldmine. These days, you can learn everything you need to know about running a business from podcasts, which are free.

Little by little, you can piece together lessons learned the hard way–but by OTHER people.

You get to learn it the easy way (aka via a podcast).

3. Find a community and some business BFFs.

I joined a community that was advertised on the Hot Copy podcast (The Copywriter Club) when I realized that they provided access to all the resources I could ever want.

Contract templates, invoice templates, interview questionnaires, pricing calculators, and tons and tons of resources about copywriting.

I lurked in their FB group as I watched and listened. I read their emails and newsletters.

The more you see how many people are already out there running healthy solo businesses, the more it becomes abundantly clear just how possible it is.

Three 40-something white women posing in front of trees on a hiking path, morning sunlight streaming in, all three with big smiles and clothing shades of blue, green, and gray. Me thinking, "I was afraid to quit my job and look at me now!"
Me and my inspiring copywriter mentors, Sarah Wayte (L) and Belinda Weaver (R), at the Confident Copywriters Roadmap Retreat in Sonoma County, CA. Photo by Sarah Wayte.

Eventually, I moved to Belinda’s Confident Copywriters (which comes with its own massive library of resources), and that’s where I’ve hung out and made friends for 2+ years.

(AND I just shared a house last fall with Belinda and one other brilliant copywriter, Sarah Wayte, in wine country for a beautiful long weekend, so I’m famous now.)

4. Take courses (but not all of them).

My first course was Marie Forleo’s B-School (where I, of course, tacked on the Copy Cure course with Laura Belgray)–fabulous intros to creating and marketing your online solopreneur business.

Then, I did Belinda’s Copywriting Master Class and eventually got a lifetime membership to Copyhackers’ Copy School.

There’s a fine line here, as it’s easy to become addicted to signing up for courses.

The goal is to achieve a baseline of knowledge and then keep it fresh by building coursework into your schedule on a regular basis—while not spending all your money or buying courses that you never complete (and remember: there are TONS of freebies out there!).

5. Get your side hustle on.

I booked my first client through the family/neighbor grapevine, offering a discounted rate as my first “learning project.”

I noticed that, even though I was working early, late, and on weekends, I found the work invigorating!

My next client came through a post on my local mom Facebook group. I exuded the confidence of someone who’s still learning but has great instincts. (And a regular and unrelated paycheck.)

One client at a time kept showing up, thanks mostly to word of mouth. I did work that I’m still totally proud of, collected glowing testimonials (more gold), and refined my process and offerings, over a period of 3 years.

6. Make friends with your numbers.

This is where most of the anxiety came in for me.

As a solo parent, I had no one else’s income to lean on if things didn’t work out. The dependability of paychecks every two weeks (plus benefits! Health care! 401k! etc!) was enormously hard to leave behind.

Every day, I considered sticking with my reliable paycheck. We were in a long-term relationship at this point.

I laid awake at night wondering which would be worse: risking sending my little family into financial ruin or never giving my dream a shot?

I avoided crunching the numbers for a long time because I was afraid the answer would be “I’m not ready to quit my job” or “this will never work.”

But once I went through the exercise, it felt so much better to have a goal. I felt empowered to plow ahead.

Here’s what you need to launch with confidence:

  • A solid sense of your expenses (start keeping track of this now if you don’t already)
  • Whatever you determine to be “enough” savings to get you through the transition (could be 6 months’ worth of living expenses, for example)
  • The monthly income you’ll need to earn (taking taxes into account) in order to afford your life.

Determine your target income and then reverse-engineer your year to hit it.

Once the numbers are written down, you can work with them.

Anything is possible: raise your rates, change your offering, hire an assistant–you’re in control!

7. Check your timing.

Only you know what life circumstances are important to factor into your timing. When my youngest was 2, I was starting to get close to ready, and then? Pandemic!

I (smartly) stayed put. I used all the time at home to continue taking online courses and working for clients. In 2022, I felt the stars align. I quit my job.

My end date felt like it decided itself.

Building the bridge

About a year before I quit my job, Courtney noticed that I kept referring to it as “jumping off a cliff.”

Because that’s what it felt like–letting go of relative security and falling into the unknown.

She asked if we could shift the story I was telling myself.

“What if you thought of each baby step as building the bridge?

Reader, I can’t fully explain it, but something massive shifted in me with that question.

It gave me agency to create the future I wanted. I stopped being afraid.

I credit Courtney with curing me of “the fear of no paycheck!” (She says it was all me.)

And the reality of working for myself is even better than the dream! So, if this is your dream too, GO FOR IT!!!

I do think there’s a leap of faith involved… AND it helps to do some planning ahead.

Be bold. The world needs your talents out there!

6 Responses

    1. Thank you, Pennie! The building a bridge language changed my life. I don’t know what magic was in that concept, but it definitely put me back in control. Hope it helps you!

  1. Katie your generosity of spirit, wit and natural effervescence shine through. This is a beautiful post, so full of deep wisdom yet in a fun and actionable set of steps. We are all in this together: evolving, stretching, growing, and taking our right place in the family of things. I’m SO delighted to watch you as you shine and share more of your medicine with the world.

    1. Thank you, Courtney! I was so fortunate to be connected with you as my coach years ago, look at these results!!! And now others will benefit from your wisdom via my story. Your coaching is magic and so are you. xo

  2. Katie has always been an observor of her world. She likes to survey all there is to know before taking action. She did this on the playground when she was two and you have just read how she started her business only after four years of careful study.. When she finished constructing her bridge, she knew she was ready. With a lot of support from her community of friends, family former colleagues, and generous copywriters she took the big step. Along with preparedness, Katie also brings her intrinsic gifts, her natural interest in people and powerful focus on what they have to say. Combined, these talents make her a warm and inviting person to interact with. These qualities have been part of her make-up from the beginning and serve as a huge plus in her new task of working well with her clients.. As her Mom, I sing her prasies from my own observations and maybe just a hint of bias. Her Dad and have always admired the way she has conducted her life. She has faithfully subscribed to the old saying, “Slow and steady wins the race..” as she keeps moving forward and making progress… And certainly, watching her transition into an entrepreneur and copywriter, her step by step approach shows the power of the strategies she writes about in this blog post. Her journey fills us with enormous pride. I am delighted too, that she has generously shared her steps with you..

    1. Thanks, Mom, for always encouraging me to pursue my love of writing! And understanding my need to observe for a while before jumping in! Love you 🙂

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