How to Transition from Experimentation to Expert as an Entrepreneur

expertiment expert entrepreneur transition - stacy kessler.001.jpeg

Entrepreneurial burnout and doubt

Over the years I’ve noticed that most entrepreneurs building service businesses go through a tough period in their business building journey. After experimenting with doing different kinds of work with different kinds of clients for a few years, they feel stuck and like they are going in circles (even if they are already bringing in significant income!). They aren’t sure how to move forward and what to focus on.

Here are some quotes from past clients at this stage of business development before we started working together:

“[My business is] going well but I'm still grappling with some major questions. Chief among them is the extent to which I should niche down. If I do that, it's probably to specialize in naming, because I love that so much and it's also the most differentiated. But I also get a lot of business, and quite easily, from strategic facilitation which is quite profitable and also pretty differentiated, but it stresses me out.” - Rebeca Arbona, BrandTrue

“[My challenge is] having a ton of ideas but really no cohesive framework for the business.” - Sara Hine, Aras Creative

“I have a lot of work to do right now, but it's mostly *doing* work and not *thinking* work. I enjoy a mix of both but carrying around 6+ clients' businesses in my head is exhausting even with all my systems and processes. I enjoy helping people, and can do a lot of different things around marketing but IT'S TIME to niche down and get specific so I know what I'm saying and who I'm talking to in my own marketing (which I do none of because I don't have a clear path for prospects to follow) AND can have a set internal roadmap clients follow to lighten my braining all the time. Offerings are too custom right now. I want to get clear on what's the best use of my time; what has the most viable ROI for my time; and what services to offer based on that. I need you to dissect and reflect what my sweet spot is! I can't decide and there's not a standard to base my decision against. I can spin on too many options and do nothing…so I need help to hone what’s really important so I can get clear.” - Rebekah Rius, Sidecar Marketing Solutions

Can you relate? If you’ve experienced this, it doesn’t mean you are doing it wrong. It doesn’t mean you aren’t cut out for entrepreneurship. It doesn’t mean you need to get a job.

But it DOES mean that something needs to change.

Phases of building a business

If you feel burnt out, stuck, self-doubt, emotional frustration, and lack of a clear business strategy, it’s not necessarily a bad thing. In fact, I find it often means you’re just ready to move from the experimentation phase to the expertise, or refinement, phase of business.

I’m sure you’ve heard different versions about the phases of of business such as idea, launch, grow, exit, etc. but the nuances for small service businesses built by solo entrepreneurs are rarely touched on. Our bootstrapped businesses built around our expertise and passions are much different than tech startups and thus we can sometimes feel like we are alone on an island doing it all wrong.

By identifying where you are in the business cycle, you can reduce your self doubt and get clarity on your next move.

For this article, I’ll be focusing on three phases of building a small service business: Conceptualize, Experiment, and Refine. And these phases can repeat over and over again. I find that most business owners get stuck between Experiment and Refine, like the women above.

Conceptualize, experiment, refine, repeat

Here’s a quick overview of these phases:

Conceptualize: Hypothesize what services you can offer based on your ideas and knowledge.

Experiment: Test out your concepts with clients.

Refine: Take what you learned in the experimentation phase and refine your business

(and sometimes, Repeat)

Let’s dive into each of these phases in more details so you can identify where you’re at and hopefully find some clarity on what’s needed next.


Say you have marketing expertise and want to go off on your own. Great! Your work is far from over. There are a million ways to build a marketing-based business.

If you want to build a successful business you actually love, you shouldn’t just do what everyone else does. You need to find what works for your unique skills and interests. A good place to start is to Find Your Sweet Spot (follow the link for a step-by-step guide that will help you conceptualize a business unique to you).

You’ll then be able to hypothesize what kind of clients you’ll work with which will then enable you to brainstorm what services you’ll offer, and determine how to price your services. If you get stuck on these last two, reach out to your network and schedule a coffee chat with some people you think would be ideal clients to learn about them and their needs (Helpful Articles: 10 Secrets to Good Qualitative Marketing Research & Market Research Reimagined: 7 Creative (and Free!) Ways to Learn About Your Ideal Clients). This will give you the information you need to develop ideas for how to approach your services.

That being said, no matter how much thinking, researching, strategizing, and hypothesizing you do - you can only get so far in this phase. You will learn the most and get good at things by doing, not thinking.

If you’re stuck in The concept phase

You’re over-thinking it and trying to figure everything out on paper. Just get the basics down and then get out there and actually try it.


Now that you’ve conceptualized what kind of business you want to run, it’s time to put it into practice. If you have a lot of expertise and connections in your field, you may be able to dive right into getting paying clients. Others will have to do some free work to test out their services (just be sure you don’t hang out in working-for-free land too long).

The experimentation phase will involve lots of little changes over time.

Some people only spend months in this phase, but most will usually spend years.

Yep, that’s right. Most entrepreneurs spend YEARS in the experimentation phase. But no one talks about this.

This is why so many get discouraged. They feel they should be further along. They feel like they should have it all figured out. They feel frustrated and burnt out. But it’s normal. At some point though, you’ve gained enough information to refine your business and when you fail to take this next step, that’s when you feel utterly stuck and like you’re going in circles.

Tips for the experiment phase

The key to the experimentation phase is to extract as many learnings as possible. Think of it like on-the-job market research. Learn as much about your clients and how you can serve them before, during, and after you work with them. I suggest developing some information gathering questionnaires that you can send to all clients before you start working with them, mid-project, and after you’re done. Here’s a helpful video on How to do Easy Market Research with Your Clients.

Schedule regular time to review this information and feedback along with your observations and reflections from doing the work and interacting with different types of clientele.

Why it’s difficult to transition from experiment to refinement

Moving from experimentation to refinement is the toughest transition for many entrepreneurs. Why? Because you have to make some tough choices. But it’s totally worth it. I suggest you find a strategic thought partner to help you think through your next steps.

This isn’t because you’re not a totally capable and intelligent business owner, it’s simply because you’re human. When we work in isolation, we are usually just too close to our work to see what we should do. Instead we try to muscle through it by working harder, thinking more, strategizing longer.

But at the end of the day, you’ll just feel emotional turmoil trying to make these tough decisions by yourself (even when you “know” what you should do but just can’t seem to do it or feel comfortable with the decision). Instead, seek out support from a trusted business expert. The key here is to find someone that will help you figure out what is best for YOU, not just give you generic business advice. Seeking generic business advice only contributes to the swirl in your head.

Entrepreneurs getting stuck in this phase is exactly why I do what I do. As an Entrepreneurial Strategist, I support business owners who are struggling with what their next business move should be. I help them find clarity around their business strategy and relieve their emotional turmoil and second-guessing self-doubt by helping them see the best opportunities and realize the truths that are already inside of them.

You don’t necessarily need to hire a business strategist to help you through this transition though. You may already have a business coach or mentor that can guide you. Either way, read on for tips on how refine your business if you’re getting stuck here. If you do decide to hire someone, read Strategist vs. Coach vs. Consultant: Which Do You Need?


After you’re done enough experimenting, it’s time to refine your business by choosing an ideal client to focus all your efforts on. I talk about the importance of this in my article, Why it’s Important to Figure out Who Your Ideal Client Is. Once you choose an ideal client, you can target your offerings and marketing towards that type of person (or business) and their specific needs.

After experimenting, you should know enough about their needs to craft productized service offerings. This means that instead of writing proposals and charging hourly, you take what you already know about the most common needs and the best ways to solve for them and pre-package your services - offering a set value for a set price. This is more appealing to potential customers as they know exactly what they’ll get and for how much. You know it’s priced to be profitable because you’ve done the work several times over (Still not convinced? Read, The Secret to Pricing Like an Expert). In a future article, I’ll share more specific tips on how to package and price your services via this productization method as well.

As you continue to deliver on the same offering over and over again, you’ll get better and faster at it, further setting you up as the go-to expert and making the offering even more profitable and streamlined.

If you haven’t figured it out yet, this refinement stage is really about niching down, something that scares a lot of entrepreneurs. It seems counterintuitive, but you are more likely to grow your business by owning a niche than by being a generalist. For more details on the benefits of being a specialist versus a generalist, read this article, 3 Benefits to Being a Specialist Instead of a Generalist. For more inspiration on different ways to think about choosing your niche, read What a Niche Looks Like for Service Businesses.

How you’ll feel once refined your business

Remember the challenges the three women described at the beginning? Here’s how they felt once they transitioned to the refinement phase of business.

I kind of knew what to do but didn't have the courage to do it, in part because it was scary and formless.Working with Stacy to get my head straight around my business was the best investment I could make! As someone who’s a brand strategist myself, I was trying to muscle my way through answering all my hard questions on my own. But just like every writer needs an editor, I needed Stacy's wisdom, objectivity and insightful probing to really understand what the best path forward for my company would be. The thing that truly surprised me in working with Stacy was not at all that she gave me powerful, strategic clarity. I fully expected that. What blew me away was that I also came to so much emotional relief when we worked together. Stacy knew how to pull out of me the truths that I couldn’t deliver on my own. When we were done, I truly felt that the plans we laid out were the right thing to do. No more agonizing. No more second-guessing. I didn’t expect that, and it was an incredible relief!” - Rebeca Arbona, BrandTrue

I feel like before these sessions I suffered from business ADD. I was constantly thinking and 'working' on the business but wasn't really moving forward. Now I feel like I have something solid that helps me take steps forward instead of in circles.” - Sara Hine, Aras Creative

“My services and process are more refined now. And you forced me to think through things I wouldn't have on my own. I feel so much more confident and my ideas confirmed. I can't wait to implement them now. Wahoo!” - Rebekah Rius, Sidecar Marketing Solutions

Think about how it would feel to have this kind of business clarity and emotional relief. Do yourself and your business a favor and go find a strategic thought partner to help you make the tough business refinement decisions.

Tips for the refinement PHASE

Niche down with an ideal client, crafting service packages for their most common needs that you want to solve for. Struggling to do it yourself? Find a strategic thought partner to help you work through it and make these tough decisions with confidence.


After you’ve refined your business and continue to work with clients, you’ll continue to hone your skills, learn new ways to serve them, and come up with new ideas. When this happens, you can choose to stay the course or repeat the three phases again.

This doesn’t mean that you’ll be starting a whole new business (though you could), it simply means that eventually you’ll want to explore launching a new offering or improving your existing offerings like what I discuss in the article, Don't Leave Money on the Table! How to Deliver More Value to Your Clients.

Tips for the repeat PHASE

In order to have a steady flow of information that will always help you improve your business and find these new opportunities, I suggest you implement standard feedback and information gathering processes into your business. I share some simple tips on how to do that in these articles:

5 Things to figure out

If you’re still figuring things out for your business, be sure to download this free checklist that will walk you step-by-step through figuring out the five foundational essentials that will set your business up for success. These are the things you’ll want to conceptualize, experiment with, and refine as you build your business. Download it free below:



IN A NUTSHELL: Tips for building a small service business

Conceptualize: Hypothesize what services you can offer based on your ideas and knowledge. TIPS: Start by figuring out your Sweet Spot and learning about the people you want to serve, but don’t overthink it. Just get the basics down and then commit to getting out there and actually trying it.

Experiment: Test out your concepts with clients. TIPS: Extract as many learnings as possible before, during, and after you work with clients. Your goal is to learn enough to be able to clearly lay out these five essentials that will set your business up for success.

Refine: Take what you learned in the experimentation phase and refine your business TIPS: Niche down to an ideal client - packaging your services based on their most common needs. Find a strategic thought partner to help you work through this stuff and make these tough decisions with confidence.

Repeat: Always be on the lookout for opportunities to improve your business or launch new value-added offerings. TIPS: Implement standardized info gathering and feedback forms into your process.

What to focus on when you conceptualize, experiment, and refine

If you’re still figuring things out for your business, be sure to download this free checklist that will walk you step-by-step through figuring out the five foundational essentials that will set your business up for success. These are the things you’ll want to conceptualize, experiment with, and refine as you build your business. Download it free below:


stacy kessler - pathfinding strategist

Hey There!

I’m Stacy Kessler, an entrepreneur, strategist, and adventurer dedicated to helping you figure out how to craft a unique, compelling, and profitable business you love around your expertise and passion.

You are meant to do important and amazing things in this world and I’m here to help you do just that.


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