3 Times When the Grey Area Held the Answers

Even when you’re running or starting your own business — something you designed from the ground up — it’s common to feel like you only have so many options. Despite the fact that you call all the shots, you can lose sight of this once you’re in the thick of the day-to-day or when you’re feverishly preparing your launch. Even if you’re in the very preliminary stages of planning your new venture, you might think that you have to do things a certain way. But why?

What makes independent professionals think there’s a “right” way to do things, especially when their ability to think creatively is probably partly what motivated them to start a business in the first place?

Sticking to conventional thinking often feels safer. If an approach is time-tested, it’s easier to gauge whether it’s a low-risk or high-risk move.

But at the same time, it’s also super restrictive, and can lead to you feeling stuck on how to manage a challenge. And in my 3+ years running my own business and coaching clients on how to start and grow theirs, I’ve discovered that no situation is strictly black and white.

Clients often tell me that I’m good at seeing the grey area. I’ve always believed in doing things my way, and I don’t mind breaking with convention to find a solution that works for me. I help my clients do the same, and I love watching them be surprised by how many options they really have.

These three stories from my clients are great examples of how the gray area can hold the answers:

1. Scale back on a full-time job.

I had a client who was struggling with how to maintain stability while she built her business. She wanted to be able to rely on health insurance and a steady income during that time period, but she didn’t know how she could juggle the hours of her old full-time job with the demands of building something totally new and working to set it up for success. She knew that some people are bold enough to quit their jobs before their business is profitable, while others work day and night to essentially work two full-time jobs. Neither option sounded good to her.


I suggested that she consider scaling back her current full-time job to a part-time job while she built out her business. After we discussed the freedom and flexibility of this option, she approached her company to see whether they would allow her to do this. They agreed (they didn’t want to lose her, either!), and for six months she worked three days a week at her company while spending the rest of her time preparing to launch her own business.

In her case, exploring the gray allowed her to creatively structure her schedule so that it provided the right amount of stability and flexibility. It let her get away from the “all or nothing” approach to entrepreneurship. Within the industry, there’s this harmful idea that you have to be okay with leaving all stability behind and hustling 24/7, and if you’re not, you’re just not cut out to be an entrepreneur. And I can’t emphasize enough that this isn’t true. You design a business model, philosophy, and schedule that works for YOU, not anyone else.

2. Explore new ways of doing things.

I have clients who have been running their businesses for ten years who believe that their way is the only way. They stick with the exact same processes they developed at the outset of their businesses, and they never outsource anything. Not a single thing. Even when a process or project isn’t set up efficiently, they try to see it through on their own rather than hiring outside help. While I admire their determination, it’s my job to help them figure out the flaws in their business models and how to address them. When these clients come to me, they know that things aren’t going well, but they’re too deep in to see exactly what’s causing the issue.

And many times, the fact that they’re resistant to exploring different options is at the root of their challenges. Being set in your ways isn’t always a bad thing, of course — these clients have the tenacity and they know what they like and what they don’t. But again, an “all or nothing” mindset doesn’t work here. You have to flexible enough to evolve when something has demonstrated, time and time again, that it causes headaches.

With these clients, I work with them to evaluate what’s working and what’s just creating a hassle. If something is working well, we let it be, as there’s no need to change things up just for the sake of it. But if it’s not, we work together on creative problem-solving.  

For these clients, the first step in improving their businesses is acknowledging that other ways of doing things aren’t always inferior to their current setup. By seeing the possibilities within the gray area, they discover new techniques to apply to their challenges while leaving the good and functional parts of their business intact. Again, “all or nothing” is a myth here. You can absolutely think creatively about solutions for underlying components or aspects of your business without having to start from scratch.

3. Find and double down on what works for you.

One of the most stressful times in an entrepreneur’s life is when they start comparing themselves to competitors. If this is something you do (or have done in the past), you recognize that sinking feeling of realizing that everyone else has a beautiful and shiny website and a perfectly targeted niche. When you’re in the midst of developing your own branding, this can be a totally overwhelming experience.

Many of my clients — and entrepreneurs in general — see what they’re competitors are doing (and how they are doing it) and assume they have to do things the same way. If a tactic has already been proven successful for someone else, why wouldn’t you adopt it as closely as you can for your own business?

The reality of being an independent professional in the service business, however, is that you NEED to stand out.

You can’t try to fit in with the crowd. I see entrepreneurs with websites that are almost replicas of the websites of their competitors, with language that sounds very similar to many others in their industry. And this, of course, defeats the purpose of branding. How can you stand out when you want to be like everyone else?

That said, I do understand the impulse to compare yourself to others. I spent way too much time doing it myself before realizing that it wasn’t a worthwhile exercise. While I’m definitely interested in what my competitors and peers are doing, I have to draw a line at comparing myself to them. My clients go through the same thing. I had a client who envied another entrepreneur’s huge Instagram following, but after discovering how much time and energy that person put into building it, realized that approach was not for her. Cultivating a huge following just wasn’t a priority in her business, and once she made that decision, she could focus her energy other places.

Again, that’s the beauty of rejecting an “all or nothing” approach. I’m aware that my coaching business has some similarities with other businesses, but I don’t subscribe to the idea that my business model or website has to look and sound exactly like everyone else’s. By allowing myself to explore all the options at hand, I’ve discovered aspects of my business that are 100% unique to me, and I’ve written things that could never appear on anyone else’s website. And it’s my goal to help all clients get to this place too, especially if they feel stuck and boxed in by what their competitors are doing. Their businesses are their own and no one else’s, and once we start discussing all the options they have, the right ideas — not the replicated ones — rise to the top.