Four Mile Markers In The Evolution of Your Expert Business

Over the past few years, I’ve had the fortune of working with a lot of great clients, at all stages of business.

Though to be more accurate, I should probably say “facing all kinds of business transitions”.

See, there are a lot of models for stages that your business can be in; two of my favourites can be found in posts from Charlie Gilkey (The Small Business Life Cycle) and Natasha Vorompiova (5 Stages of Business Development).

But it’s those transition points – those inflection points and milestones– that mark the evolution of our business.


It’s the move from one stage to the next that presents us with new challenges. It’s as though you just get things sorted out … and then the game changes. You just get things working … and then a whole new set of questions emerges.

It’s easy, in those moments, to feel like you’re alone. Like these challenges that are new and fresh aren’t just new for you; they’re new in general. Often, you look around you at your peer group, and see that they aren’t struggling with these things. (Or if they are, they’re not talking about it).

But I’m here to tell you that these transition points aren’t unique, and they aren’t just happening to you.

When you’re running an “expert” business – training and teaching and coaching people based on something that you know to be true – your business will go through an evolution. There are certain mile-markers along the road that you’ll inevitably pass.

I’ve seen them crop up over and over, and the patterns are predictable. As such, they can be planned for. If, that is, you know they’re coming.

Mile Marker #1: Build Capacity

For my clients, the first transition happens usually hits you right around the time you start projecting $75,000 in annual revenue. While there are a few smaller waypoints earlier in the journey (a common one is around $30,000), none of them really require you to make a significant shift in your business like Mile Marker #1.

See, most expert businesses start as service businesses. It’s you, working directly with clients on their website, their copy, their eating habits, their whatever. You know you’re rapidly approaching this threshold when you are feeling like “there’s only one of you” and you wish there were more. You want to work with more people, but you just can’t.

Mile Marker #1 is when you inevitably start to run into capacity problems. Thus, to get through this transition you need to build capacity. That usually looks like:

  • Consider bringing on contractors (even just on a project-by-project basis). A common hire at this point is a VA who can help out for a few hours a week.
  • Start looking at ways to build leverage into your business model, without sacrificing the high-touch service that your business has become known for. That means group programs, small courses, productized consulting, etc.

Of course at this stage, you’re getting referrals, but aren’t well known enough to have enough clients just magically show up on your door-step. So to get through this transition, you also still need to work on push marketing: getting your message out into the market.

Mile Marker #2: Build Leverage

Despite what you may have heard elsewhere, the next mile marker does _not_ hit at the highly-regarded six-figure mark. In fact, six-figures is actually a much less significant threshold than you might imagine; the problem-solving lessons from Mile Marker #1 can pretty much carry you through to Mile Marker #2.

At about $150,000 in annual revenues, though, you realize you need to make another shift.

Your hybrid model of one-on-one and leveraged offerings is not really working any more. Maybe you’re just tired of working 1:1. Maybe you love the energy of the group settings. Maybe the growth potential is addictive.

Whatever the reasons, when you hit Mile Marker #2, you need to start building _leverage_:

  • Start assembling your supporting cast. More than just hiring contractors or a few-hours-a-week-VA, you want someone that is going to be giving dedicated attention to your business, your clients and your community. It may still be part time, but it’s a higher-value position you’re looking to fill, usually in customer support.
  • Design programs or products that can replace your high-touch one-on-one offers. That could be a signature product, or a continuity offer like a membership site, or something else entirely.

Building Leverage is also where many people start switching to a hybrid lead generation strategy. Instead of feeling like you need to constantly push your message out into the market, you’re able to start pulling in inquiries – people want you to speak, or guest on their podcast, or what have you.

You’ll still need to do push marketing to get you across the hump, but you’ll start to see some gains from pull marketing, too. Writing a book or taking speaking engagements is a common hybrid push-pull method.

Mile Marker #3: Build Your Team

A fully leveraged business model usually start to show its growing pains by the next doubling of revenue, at about $300,000. The challenge here is all about complexity:

Simply put, you’ve got so much going on that you can’t keep it all straight any more.

You’ve got projects and marketing initiatives and speaking engagements and books and events and … and … and …

And it’s going to completely exhaust you if you try to continue to be the only person at the top in your business.

To get through this transition, you need to build your team. And not in the “hire some people to help with administrative tasks” way you’ve been doing it so far. Not just in the “I’m going to offload the stuff I’m not really good at” kind of way.

You’re going to need to hire people who can do things that you actually are good at (and like doing!) so that you can focus on the truly high-level, visionary stuff that only you can do. Dan Sullivan calls this your Unique Ability (aff); Nilofer Merchant, your Onlyness (aff); Tara Gentile, your Quiet Power (aff). Whatever you call it, you need to:

  • Start building systems so you can turn your clients over to other people in your organization. Whether that means training and certifying coaches, or hiring a team of production artists, you need to start thinking about ways you can stop working directly with your clients.
  • Hire a team of 3-5 dedicated people who can start taking some of these high value tasks out of your hands. Think project managers, online business managers, maybe even a Chief Operating Officer. And – yes – other people who can work with your clients so you don’t have to.
  • Consider ways of building your product suite without you having to be the one to develop the product. Maybe that means licensing, or hiring a team to build your products and curriculum for you.

It means you no longer need to – because that’s how your marketing will work best, too: when people are being pulled toward your business because you’ve built that level of gravity (and gravitas) in your industry.

Mile Marker #4: Build Your Reach

Mile Marker #4 is all about scale and reach. I mean, sure, you’ve been building your reach but when you start to crack the half-million dollars in annual revenue mark, you’re on your way out of micro-business territory, and into boutique agency or – dare we say it – actual small business land.

This transition is a hard one for many business owners, and many decide intentionally not to cross this threshold. It’s a hard thing to do, to become the “face” of your business, but to let go of control of the operations. To let other people write your blog posts, or work with your clients, or run your projects, or develop your products.

The challenges here are largely because of growth; a good problem to have! You’ve reached a level of success and recognition in your specific niche, which means that it’s likely time to:

  • Explore different verticals in your product and service offerings. What other problems can you potentially start to solve for your best clients, and how?
  • Proactively structure your team for to remove yourself from management functions: with a team of 5-8 or even 10-12, questions of culture, leadership and management start to take on new meaning.

If your goal is to be the “idea person” at the top in your business, this process can be incredibly freeing. As you take “you” more and more out of your business, you’ll find that your capacity for increasing your growth expands, multiplicatively.

The Key To Successfully Navigating All the Mile Markers Is This

Now, you may read through those Mile Markers and find that some parts resonate more than others; that’s to be expected. Everyone’s journey happens at a different pace, and not everyone shares the goals of getting to Mile Marker #4 and beyond.

But here’s what’s true, no matter which point along the journey your business is in, or what your goals are:

As you approach each transition in your business, you will be tempted to try to blast through each one by finding for new ways to create; new offers, new products, new marketing methods, new, new, new.

And that will work, for a time and to an extent. But it’s also a really good way to spin out before you actually complete the turn. Continuous, rapid growth fuelled by the cult of the new is a fast-track to not only burning yourself out, but also diluting your brand and your message. A scatter-shot approach doesn’t help anyone: you, your customers, your audience or your team.

The simple truth is that in order to move through any of these thresholds, you need a lot less, not more.

Less of “you” in the business, so that you can help more people on a scaleable level. A narrower focus on fewer things, so you can do them better and more powerfully. A simplified sales funnel not only leads to streamlined offers that are easier for your customers to digest, but to a business model full of products that sell themselves.