6 things I wish I knew before quitting my job without a backup plan

• Lindsay Yaw Rogers is an entrepreneur and brand story coach based in Aspen, Colorado.
• After quitting her job in tech, she says becoming an entrepreneur was a journey of trial and error.
• Rogers says it's important to have a solid business foundation to enable steady, long-term growth.

I'm a risk-taker. But leaving my high-paying job at a tech startup in 2012 with a one-week old baby — with no plan — meant my family's income went from comfortable to zero overnight.

My husband was developing a wind farm in Chile and not getting paid. But I knew I needed to leave the toxic workplace I'd been in for two years.

Nine years into running my business, a brand story and content strategy firm, I've had time to look back on the mistakes I made, the stints of success, and the six things I wish I'd known before going out on my own.

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1. Nobody is their strongest alone

Early on, a phone call to my old boss landed me multiple massive content projects for several large companies. So in the first few years, I didn't have to work hard to get clients — which meant I also became overly confident. Eventually I had nothing in place to help me get more work, but I was stubborn, wouldn't admit that I was frustrated, and didn't seek out a mentor because I thought I knew everything or could figure it out on my own. This caused me to lose several years of growth and income.

In the past few years, I've joined a mastermind group, read and listened to countless business books and podcasts, and have taken close to a dozen online courses — all part of my quest for mentorship.

2. Normalcy isn't the goal

Fitting in is the best way to be forgotten. After a client chose not to renew my contract because I "wasn't 100% necessary" for their growth, I took a business course online. It made me realize everything I was not doing — like differentiating myself .

My first task was to define my "Dream 100" — the list of people I really wanted on my client list. Easy. Then I had to define what my secret sauce was that would make me different. It took me six months to nail down the process I'd used with past clients and put it into a legible framework I could sell to a higher number of different clients.

3. Fail quickly, fail often

My dad used to say, "you never learn less" after anything disappointing happened to me, and it would drive me insane.

But after getting humbled several times as an entrepreneur (ie. losing a job bid), I realized he meant that experimenting is how you find your edge, even when some of those experiments completely bomb. Once I accepted that failure was inevitable, I felt less trapped by perfectionism and more free to try new things, create new programs, and go after my "Dream 100."

4. Be more interested than interesting

Years into my business, I started listening aggressively to my ideal clients, and moved from trying to be interesting myself to being wholly interested in what they needed. This moved my client roster from start-and-stop to a steady stream, and thus recurring revenue.

5. Be prolific

A few years back, I went back to my roots and started writing again — this time with a strategy. I began penning blog and guest posts for brands and entrepreneurial magazines, sending weekly emails, and answering HARO requests. This has allowed others to see how I work and think, what frameworks I use, and how I impact others, which has led to even more opportunities. Just recently, an article I wrote got selected to be in a book being published by Thrive Global.

6. The back of the statue matters

When I first started working solo, I hated all the unsexy stuff that needed to happen on the back end of my business. But when I started to have a referral drought, I admitted that having no system (the back of the statue) was impacting my reputation and positioning (the front of the statue that people could see). It took months of toil, late nights, and a full-time virtual assistant to get my systems dialed, but now I communicate my process with clarity.

Lindsay Yaw Rogers coaches high-achieving entrepreneurs and athletes on how to create powerful brand stories to to stand out, create partnerships, and position themselves as a leader.

This article originally published July 8, 2021.