Turn A Business Setback Into An Opportunity

Photo by Chris Adamus

After almost a year of working together, my virtual assistant and I were finally a team.

We had figured out how to use shared Dropbox folders.

We got to know each other’s communication style.

I knew her dogs’ names. She knew mine.

We overhauled my website, launched my blog and were about to launch my newsletter.

Then she quit.

“Wait!” my confused brain shrieked, “didn't you just tell me that I was one of your favorite clients?!” (She had.)

Communing At WDS

When I first met Lindsay, we were at the World Domination Summit (WDS) in Portland, OR.

On day one, we were in a long, unmoving line and struck up an easy conversation.

We owned the same Old Navy hoodie. We had shared values, and we were on the same trajectory: small business ownership.

What separated us in that moment was that she wanted to work with me, but I didn’t want a virtual assistant. Still, we became fast friends.

A week later, Lindsay emailed. Would I like to check out her resume and portfolio? Sure, I thought, not thinking that we would team up. But, a few days later, we Skyped, laughed and signed up to work together.

Life (and business) had been good. Now it was even better.

Fast-forward eight months, and I am on spring break with my kids. The Many Hats Coaching newsletter was set to launch in two weeks.

Then I got Lindsay’s ‘notice of departure’ email and my chest squeezed the air out of my lungs in one long deflated breath.

Setback? Or…

Admittedly, my first reaction was emotional: I was devastated, then afraid, then angry. Then I changed all my passwords to accounts she had access to. WTH just happened?

In the scheme of things? Didn't matter. I had to start hustling.

Back at my desk, I ground down. After all, I had a newsletter to put out! And, goddammit, I was going to make it happen.

In the end, I *did* get the newsletter out (later than planned), but I gained way more than traction on my email list. Biggest lesson? With time, comes perspective, and then hard-won wisdom.

Biggest lesson from a setback in business? With time, comes perspective, and then comes wisdom. (Tweet that)

This is what happened when I refocused and got back on track:

1.     I reconnected with my business. By taking on a virtual assistant, I tossed things off my plate that intimidated me. Having a “beginner’s mind” sometimes sucked, so I delegated. In doing so, I missed an opportunity to build foundational skills and headspace needed to run a business.

One suggestion I have for new business owners is this... Don't hand off operations or basic assignments until you know how to do them yourself. Learn to love getting your hands dirty.

Tip: If you have a virtual assistant, have him/her write down all the steps in a process that you don’t know and file where you can find it, pronto. Thank goodness I had the foresight to have this done.  

2.     I reconnected with my “why.” When I declared that business ownership was my next step, one of the reasons why was because I wanted to learn. I wanted to grow. I wanted to expand my entrepreneurial knowledge and mindset. What ended up happening instead was that in some ways I became co-dependent. That’s not the easiest thing to admit, but there you have it.

3.     I gained confidence. Know what happened when I figured out Mailchimp? I felt pretty amazing. One day, the sentence running through my head changed from “I can’t figure this out” to “I’ve got this.” This happened again and again as I reconnected with daily operations and stretched into new areas. Yes, doing this took precious time, but it has absolutely been worth it.

4.     I remembered how to ask for help. Without being able to delegate, or get an immediate answer to my questions, I got stuck. Then, freaked out a little. I needed help! So I reached out to fellow entrepreneurs and others in my online community. And by doing that, I got over myself. It was uncomfortable letting the world know I didn't have all the answers. But you know what? I don’t have to. No one has to. We just need to learn how to ask for help.

Tip: Check out Amanda Palmer’s book called The Art of Asking.  It’s a phenomenal read on how to open your heart, ask for help, and connect with others.

5.     I realized that it’s okay to fire your clients. Maybe Lindsay “departed” or maybe I was fired. Maybe, too, the language around our separation doesn’t matter. But, here’s what I’m taking to heart: You can't be afraid to be the one to let go. If clients aren’t bringing out the best in you, then you have no reason to work with them. Lindsay’s action reminded me of this critical tenet of being a smart business owner. Am I working with clients that bring out the best in me? Yes, I am now, thank goodness. But, it’s essential to always ask the question and be ready for the answer.


Sometimes these lessons are hard to swallow. Sometimes it takes a bit of time to process them and see them in a more objective light.

Sometimes, things simply work out for the best.

Someday, I will hire another virtual assistant. For now, I'm grateful that this “setback” turned into an invaluable opportunity for growth. In business and entrepreneurship, there is never a dull moment.

In business and entrepreneurship, there is never a dull moment. (Tweet that)

Lindsay, if you’re out there reading this, I just want to say thank you for helping me get my business to where it is today. I still think you’re awesome.

What setback in your business or career stopped you in your tracks? What did you learn from it? Please share in the comments. Thanks!

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