Entrepreneurs & Business Owners: How To Know When It’s Time To Replace Yourself

10 years ago, I founded my company — MemberMouse. We’re a software solution for WordPress that helps online entrepreneurs and business owners build powerful and profitable membership, subscription, and recurring revenue businesses. While I had dabbled in an interesting variety of entrepreneurial ventures before this (a story for another time), this was really my first go at creating a sustainable business. 

As I’m sure you can imagine, I’ve learned a lot of lessons over these past 10 years. One of the main lessons has to do with knowing when it’s time to replace yourself in your business so you can grow and evolve into a larger, more impactful role. Since I essentially started out as a solopreneur, this evolution happened for me at nearly every stage of the business. 

Whether you’re also a solopreneur or already work with a team, you know that running your own business can feel like a never-ending juggling act. While it may be a necessity for you to wear all the hats in your business, eventually there will come a time when you actually become the bottleneck to growth. If and when this happens, you’ll need to pass the torch on to someone else or risk treading water and missed opportunities. 

That’s why in this post I’ll share 5 key things I’ve learned with you about how, when, and why to replace yourself. And as you’ll discover, navigating this process is not quite as simple as it seems. That’s why we’re starting with this first key insight…

Trust your inner guidance

This first idea might seem peculiar to you, especially coming from someone offering advice. But in my experience, it has served me well to listen to and trust my inner guidance when making important business decisions. The surprising thing is that this wasn’t something that I ever intended to learn. If I told myself ten years ago that this was going to be the most important thing, I wouldn’t have understood it.

In the beginning when I was starting my business, of course I had a vision of where I wanted to go. I had an idea of what I wanted to accomplish. But, I lacked experience. I really didn’t know how to approach it, the steps that I needed to take, the tools that I needed. By looking for answers in external sources, I realized that I wasn’t really bringing myself to the business. I wasn’t really asking myself how I would do things and trusting that, in spite of my inexperience, whatever my answer was could still be good. 

So if you have an intuition or feeling that your time can be better spent on higher-value tasks in your business, trust yourself. It might really be time to look at replacing yourself so you can grow into a bigger and more impactful role. However, know that it is possible to replace yourself too soon. What do I mean by that? Well, let me tell you a quick story from the early days of my business.

Understand when it’s too soon…

Back when I first started MemberMouse in 2009, I was actually working a full-time job as a consultant. I used the money I earned in my day job to bootstrap the business. From the very start, time was my scarcest resource since the majority of it was allocated to just making the money to fund the business.

Right away, I “knew” that I needed to hire developers to help build the platform. Even though my background is in software development, there were so many other things that needed to be handled. I immediately recognized that I couldn’t develop the platform all on my own and manage all the other crucial tasks necessary to build a business.

I hired a team of developers to build version one of the platform. I outsourced it to the team and paid for it with the money I was making with my day job. I won’t get into all the gory details here, but the developers came back – $20,000 later – and handed me something that technically worked, but was fundamentally flawed.

What I realized from this experience was that I thought I wanted to run this race myself, but actually I wanted somebody else to do it for me. This is a key distinction in knowing whether or not it’s time to replace yourself in your business. It wasn’t like I was already running and thinking, “You know what? I’m tired, I need to pass this on.” It was more like, “I should just be able to get somebody else to do this.” I was trying to find somebody else to do the work for me. The fundamentals of the platform and my key offer was where my attention needed to be.

Ask yourself, “Am I passing this off because I just don’t want to do it? Or, is it actually time to get somebody to do it?”

Know exactly what needs to be done

Another major lesson I’ve learned is that it is hard to find the right person for a particular job if you don’t have a clue as to what really needs to be done. So, there is an actual value and purpose in at least dipping your toes in all the different areas of your business. If you haven’t actually spent at least a little bit of time playing the role yourself, there are three pitfalls you can encounter:  

1 – You don’t even know if the role is needed in the first place

2 – You can’t possibly know who you need to look for

3 – You can’t know if that person is doing a good job when you do hire them

I’ve learned that it isn’t quite as simple as just handing off tasks to someone. It is important to truly understand all of the different roles that need to be played on the team.

I also recommend that you assess your strengths and weaknesses. Ask yourself what you are really capable of. Where in your business is it going to be a losing battle if you try to do it? Remember, you want to grow and evolve into a bigger role that will have a greater impact in your business. You’ll make things much harder for yourself if you choose not to work from your strengths.

This is when you need to be honest with yourself. There are probably areas in your business where it feels like you’re rowing a boat, and you’re not going anywhere because you’re holding the oars wrong or there’s a hole in the hull or something like that. That’s the point where you need to consider finding someone to take over and complement your weaknesses.

Look for the warning signs of trench tasks

Once you have real momentum in your business, there are a ton of things you could be working on at any moment. But what if you’re stuck responding to emails for ten hours? Or scheduling all your social media posts for the week? When this happens, a large portion of your time is being spent in what I call “trench tasks.”

How do you know when you’re in the trenches? Basically, if every day when you go to work, you have a consistent and repetitive set of things to do, you are in the trenches. When this happens, you have a perfect opportunity to find somebody else to do them for three reasons: 

1 – The role is clearly defined, it’s task-oriented so there’s basically a list of things to go through

2 – You can easily know what skills are needed to accomplish these tasks

3 – You’ll be able to measure if somebody’s doing it and how well they’re doing it

If you have all these tasks you’re doing every day and you know that these other things would be more valuable, it would serve you well to find somebody to do the tasks. Ask yourself, is your time being used in the most valuable way to further the strategic vision of your business?

Think about your opportunity costs

As you’re thinking about replacing yourself in your business, it might be helpful to consider your opportunity cost. Where are you missing out on opportunities when your time is consumed with tasks that could be delegated?

Don’t get me wrong… In the beginning, you may not have a lot of different opportunities and avenues to explore, so the best that you can do is just take care of the menial stuff. But as time goes on, you’re going to get indicators of opportunity. And so, if you have all these consistent tasks, you’re not going to be able to act on those indicators of opportunity. This is an opportunity cost.

Even though I was creating a software platform, I think this applies to any product or service you are creating. In hindsight, one of the primary mistakes I made in the early days of MemberMouse was not releasing something soon enough. When the majority of your time is consumed with day-to-day tasks, it can be easy to procrastinate releasing something that will move your business forward.

At the end of the day, something needs to get out in the world and you need to get it in front of people so that you’re getting some sort of response, so that you know and you can guide your strategic decisions in terms of how to move forward. Because the quicker you can get something in front of even one person, the sooner you can get the feedback needed to either stay the course or change directions.

Final thoughts

I hope you’ve found these ideas and insights to be helpful. It is my hope that these lessons and stories from my journey can help you along your own path. Many thanks to Andrew & Pete for giving me the opportunity to share here on their blog. If you’d like to learn more about what I am up to, check out my podcast and take a look at our website. I recorded a really fun and engaging interview with Andrew & Pete earlier this year. You can listen to it here if you’re interested.


Eric Turnnessen is the Founder & CEO of MemberMouse. Over the past 10 years, he’s worked with thousands of entrepreneurs and online business owners who build membership, subscription, and recurring revenue businesses. In his free time, he enjoys composing music, a nice cup of tea, and catching up on Poirot reruns.

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