How I Made My Toughest Business Decision Yet

As I sat there and listened to my mentor, I felt like she was asking me to cut off one of my own arms. She suggested that my business had grown to a point where I could no longer afford to offer two things I was passionate about. If I wanted to continue to grow, it was time to choose one. 

I knew she was right. 

I also hated the choice. 

A lot of my clients who are service providers go through this phase when they rebrand with me. There are many things they’re great at — many things they love doing — but for their branding to be cohesive and their business to be sustainable, they have to choose the offering that’s most aligned with who they are and what will serve the most people.

My business has always done two things: 

  1. Styling for women entrepreneurs with established personal brands, and 
  2. High-level brand development work for women entrepreneurs with emerging personal brands. 

When it came to styling, I loved the exclusive one-on-one attention I could give women when they shopped with me in New York City. I loved helping them understand how they’re perceived and helping them look like the promise of their brand. It’s one of my favorite things to do. And something I’m very good at. 

But, towards the end of last year, something didn’t feel right. To really rock the style arm of my business there were things I’d need to do that would take time away from brand development service delivery. Things like:

  • Hire someone to build an online style quiz that could be used as an app.
  • Train and hire style interns to do the service delivery (my favorite part) since it was so time intensive. This would allow me to focus on getting new business. 
  • Build digital style tools that would help people understand how to style themselves if they couldn’t get to New York to work with me. This would make the business more scalable. 

Simultaneously, as I built the style arm of my business, I added in branding to create more value for entrepreneurs. So instead of just styling them, we also did brand assessments that helped them learn how to attract the right clients. One thing led to another (as they often do in a business) and soon I began consulting about branding without the style part. 

This became the material I felt most alive sharing. There were several classes I taught about it, and it was also some of my most well-attended workshops. But to really rock the branding arm of my business, there were things I knew I needed to do that would mean I couldn’t build out the style arm of my business. And there were dreams I had for this part that have nothing to do with style. Dreams like: 

  • Giving a Ted Talk on the topic of Purpose, Business and Branding. 
  • Interviewing Rick Warren about the concept of a Purpose-Driven Life and what it means for business. 
  • Writing a book about Purpose. 
  • Leading conferences and workshops about it.
  • Creating licensed content that could lead to more revenue. 

Both dreams obviously lead to very different places. The amount of time it would take to do both well meant that they couldn’t both be done simultaneously. The truth was I was reaching more people through branding than I was through styling and when I looked at my role models, women like Diane Von Furstenberg, Donna Karan, and others, they didn’t have an entire arm of business in a completely different industry. 

I was at a fork in the road, and this was the first time I knew I had a business — not just a hobby. In service of its growth, I had to be more mature about what was realistic to do. 

My business development mentor challenged me to make a choice during one of our weekend intensives. I nervously explained the dilemma to my colleagues as they listened and empathized. They knew how much I loved both pieces of my work. Several said, “Why do you have to choose? Can’t you just keep doing both?” To which my mentor replied, “Not Kristen. She’s too thorough, and to do it well will require her undivided attention.” 

They became silent. All eyes were on me. 

I had just presented to them that over the course of that year 20 percent  of my revenue came from the style arm of my business and 80 percent came from brand development work. “Make a decision in the next 24 hours,” my mentor said. 

I knew what I had to do. The numbers told me. My intuition told me.  I just didn’t want to do it. I thought to myself:

  • What if styling is indeed the more successful way to go? 
  • What if styling will grow faster? 
  • What if I’m not skilled enough at branding? 
  • What if I failed? 

These were all real fears. I had just crossed the 6-figure mark in this business and I didn’t want to screw it up. But I knew not choosing was a way to play it safe. It would have kept me at the same level, essentially hiding. If I wanted to make a bigger impact in the world and double my revenue for the third year in a row, I had to put my big girl panties on and call this shot. 

So I did. 

The next day at check-in, my colleagues and mentor each looked at me with expectant eyebrows. “I choose branding,” and as I said it, I breathed a slight sigh of relief — and felt my heart break. 

The dream of entrepreneurship is that you get to do it “your way” — for awhile. As I grew, I learned that the mature business owner isn’t invested in “her way” more than she’s invested in her business’s success. Sometimes, you have to put your business’s needs before your own desires for both to be fulfilled. 

This single choice set the stage for my business to grow in revenue by 60% in the next year. In the end it came down to the answer to this one question: What path will allow you to do the work that makes you feel most alive and impact the most people possible while doing it? 

Have you ever had a major business decision to make? What criteria have you used to make it? Let me know in the comments below. 

Kristen Domingue is a member of the DailyWorth Connect program. Read more about the program here.

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