5 years in business (and 8 takeaways from entrepreneurship)

Recently, I filed my annual report, which means it’s been 5 years officially since I opened my business. 5 years in business (and 8 takeaways from entrepreneurship). Looking back, there are a few things I did quite well–and others that I wish I had done better, sooner, or differently.

Here are the top 8 takeaways from those 5 years in business. I started out with 7, but midway through it turned into 8. So, here’s are some of my biggest lessons in running an online business, including how my mindset has shifted over time.



8 Takeaways After Having a Business for 5 Years

So what are the takeaways?

1. Take the leap.

If this is something you’ve been wanting to do, take the leap and start your own business. Time will pass. You’ll learn a lot along the way. And you don’t want to look back and wonder what if…

What could have happened if you had started that business?

What would you learn?

Who would you be?

How would your life be different?

2. Build your network.

Start building your network from day one, reaching out to people you already know, and engaging in professional conversations with others. The importance of networking for entrepreneurs is something that I can’t emphasize enough. It’s more important than just about any digital marketing strategy–and it’s one of the single most valuable business growth strategies. You learn from one another, grow together, and share referrals back and forth. Sure, you want to talk to prospects, but only talking to prospects is one of the biggest online business pitfalls I see.

3. Pay for coaching.

Investing in coaching or mentorship is the fastest way to accelerate personal and professional growth. I am not the same person I was 5 years ago and that entrepreneurial mindset and personal development is something that I didn’t understand when I started out. Sure, you could get there eventually without a coach, but investing time and money gives you some serious gravitas.

4. Build an email list from day 1.

One of the best things I did was build an email list from the beginning. Even if it starts small, and you’re only writing to 5 people a week, taking the time to build an email list early in your entrepreneurship journey gives you a ton of content and sets the stage for the value you bring. Regularly communicate with subscribers to provide value and establish a direct line of communication…whether that’s weekly, monthly, or something else.

5. Turn everything you do into a resource.

As you run your business, document processes, create checklists, and write down your big takeaways. Maybe it’s stuff you share with your clients to make it easier to understand what you’re doing, maybe it gives you a tool to teach others, or maybe it gives you digital products. But by doing it as you go, you save a ton of time instead of reverse engineering it later.

6. Focus on process.

I grew up in traffic management, which means that I bring a process-driven approach into everything I do. I don’t write a proposal without knowing exactly how I’ll deliver on it. So yes, it’s about using tools and frameworks to stay organized and deliver consistent results. But it’s also about having clearly thought out timelines and methods for delivery so you look like a pro, and aren’t scrambling trying to figure it out as you go.

7. Charge more. Running a business costs more than you think.

The value you bring is more than you think. And if you’re coming into entrepreneurship as a habitually underpaid human or without understanding the true costs of running a business, then probably whatever you were thinking of charging, your fees need to be higher to be profitable.

8. Talk to people.

Talking to people is critical. It’s not just about starting conversations with people to drive sales. It’s about talking with your audience of clients, prospects, past clients, and people who didn’t buy from you to understand their needs, gather feedback, and improve communication and brand messaging. In fact, one of the biggest pitfalls of online business is failing to talk to people, failing to find out where you have gaps or opportunities for improvement, or failing to look for ways you can potentially stand out.

(Looking for more lessons in entrepreneurship? Here’s an article I wrote last year.)

Want to skip to a specific section? Here’s a quick overview of what to expect and where to find it.

Take a peek through the below timestamps so you can find exactly what you’re looking for to get some audio.

Chapter 1: Introduction

Reflection on the annual report (00:02)

Importance of reflection (00:34)

Decision to go live (01:28)

Chapter 2: Takeaway 1 Take the Leap

Importance of starting sooner (02:26)

Chapter 3: Takeaway 2 Build Your Network

Starting from day one (03:03)

Reaching out to people (03:29)

Practicing talking about what you do (04:00)

Chapter 4: Takeaway 3 Pay for Coaching

Exploring options available (05:47)

Chapter 5: Takeaway 4 Build an Email List

Communicating regularly with subscribers (06:55)

Chapter 6: Takeaway 5 Turn Everything You Do into a Resource

Adding value for audience, clients, and customers (07:45)

Examples of resources created (08:49)

Chapter 7: Takeaway 6 Build It in Public

Challenges of building in public (10:34)

Chapter 8: Takeaway 7 Focus on Process

Creating a process-driven framework (11:01)

Benefits of focusing on process (11:55)

Chapter 9: Takeaway 8 Talk to People

Building potential client lists (14:12)

Conducting market research (14:16)

Chapter 10: Conclusion

Recap of key takeaways (15:37)

Invitation for questions and further discussion (15:45)

Mention of podcast for more insights (16:16)

Final remarks on business journey (16:57)


Want to read along as you watch or listen?

Here’s a transcript of the video. (Beware of AI-transcription errors. This transcript has not been edited )


So yesterday morning, I walked in to my office, sat down, opened my email, and I realized that my annual report was due. And if you have an LLC or any kind of like, business entity, you have to file annual report. If you don’t know what that is. Basically it’s going in and saying, here’s what we’re doing. Here’s who’s still in charge, here’s all the things. And as a single member, LLC and S Corp, I still have to do all this, even though I’m the main person named. So what’s interesting is every year when we get to these points, I think back, it’s a really good time to reflect, more so even than the new year, new you. It’s like, what have I learned? So I usually create a blog post or a social media post, but I wanted to go live today.


Five years is a really interesting anniversary. It’s particularly interesting to look back and realize that it was a lifetime ago in many ways when I first decided to take the leap. And it was a lifetime ago because I am not the same person I was, and I’m not the same person I was, in large part because of many of the things I’ve learned, many of the friendships I’ve formed, and just everything that goes into web oh my gosh, Siri’s talking to me. What goes into running a business as I try to turn Siri off in my computer? So this year, I came up with seven takeaways. And takeaway number one is to just take the leap. That is so important because it’s scary. Change is scary.


Going from having something steady, even if you don’t love it, to something that is irrevocably filled with risk is hard. And I went through a really interesting crisis last fall personally, like, not professionally necessarily, where I started to doubt things because of some of the things that were going on with the economy. And it was a reminder, for the reasons that I got into this, that I had two small kids, that I wanted to be able to take flexible time, that I wanted to just be able to focus on the things that matter to me while still helping other people. And so taking that leap was hard. And it took me, for sure, a solid six months of like, will I or won’t I? This is scary. Will I or won’t I? What should I do? All the things.


And to be fair, if I’d done it sooner, I would be so much further ahead. We’d be facing our 6th year. We would be doing so many different things. We’d be having a different conversation today. And if I’d really started, like, if I’d kept the food blog going that I started back in 2010, where would I be now? I might be a great food photographer. I might be doing something totally different. But the point is, start sooner. You will always wish you had, and the time is going to pass anyway, so you might as well make it worthwhile. Takeaway number two is to build your network from day one, stay in touch with people.


And maybe that’s one of the benefits of social media, for sure, but of moving around so much with my husband in the military is that I have lots of people everywhere, and I already had this really interesting network, so it was not a big deal to continue to add to it, to continue talking to people and doing that from a professional basis. Do it from the get go. Start reaching out. Talk to people you may already know or that you have some tangential conversation with, even if you’re talking to people in the grocery store. Right. Get practice talking about what you do. The more you do it, the easier it’s going to be. And even if the first one or two things that you do really don’t go well, that’s fine.


You have to get that stuff out of the way so you can do the thing better, but build your network. 99% of what I’ve done has come from network building as opposed to cold outreach or any of these other things. Because when you talk to people, when you explain what you do, that’s when you come to life. That is when all of the things start to come together for you. So by building your network, you already have this soft landing place. Right? Okay, so those are the first two taking the leap. Building a network, building a referral network, too. Not just a network of people who could be potential clients, which is what I did the first time. I was like, oh, I shouldn’t talk to people who I might be potential clients with.


But what I didn’t realize is the importance of having colleagues. And it was like, well, I have my own business. Why would I talk to people who do what I do? And that’s the opposite. That is the sheer opposite, because there is enough work out there for all of us. And if you have other people, you can learn from them. You can learn best practices, you can come up with some other ideas and brainstorm and go create. Co create, but do it for individually, whether it’s co working. I worked with my friend Anna Hetzel last fall, and we co built offers that are virtually identical, but we’re both selling them and they’ve been very successful for both of us. And to that end, I’m going to shift takeaway. Number three was not to pay for coaching, that was number four.


But it is number three. To that end, pay for coaching, build that network, work with mentors, find out, because, yes, you could do it on your own, but will you? If there’s not someone holding your feet to the fire, if you don’t have skin in the game somehow, someone to help you get to that next level, you’re not going to take those steps nearly as quickly. Otherwise it’s like, okay, yeah, let’s dive in, let’s do the thing. So pay for coaching, whatever that looks like. Maybe it’s a paid community, maybe you’re starting very small. On the other hand, maybe you’re starting much bigger and going to do a mastermind, going to do this business startup program. There’s options out there and we can 100% help. I say we can help.


I’m getting ready to launch a coaching offer, but that has nothing to do with this takeaway. But if you pay for coaching, you are, I don’t know, anecdotally, 100 million times more likely to do the things that will move you forward to propel you to where you want to be in your business. So next up, start building an email list from day one. I don’t care if you have five people on it for the first two years, start building it. Start doing the things that are going to get you this email list. Because even though there’s all these oddities out there with DMARC, all the other things, when you have people’s contact information, you can actually follow up with them.


Whether you follow up with them one by one, whether you follow up with them mass communication wise with these campaigns and these fully thought out funnels, it doesn’t matter. I want you to be communicating with them regularly. Whether that’s once a month, once a week, whatever that looks like, that’s reasonable for you. And I want you to start building value because that’s where you own the thing. Social media can go away, weird stuff can happen. People can buy networks and all of a sudden they lose all their value. Not naming names, of course, but if you get locked out, if any of these things happen, you lose all of that stuff. So start building your email list, follow up with them, do all the things to continue to build that traction. So that’s four. Number four was build email list.


Number one was take the leap. Number two is build your network. Number three was pay for coaching. Number four is build your email list. Number five is turn everything you do into a resource. If you are responding to comments on social media, if you are having similar conversations over and over, if you realize that, oh gosh, I have a process for this that shortcuts this, that makes it easier. Write it down. You don’t necessarily have to sell it, right? You don’t 100% have to sell it. There’s nothing you have to do with it. But you could offer it to people as value. It can be a way that you add value for your audience, for your clients, for your customers. Be like, oh yeah, and here’s how I do the thing.


Just to give them a sense that you’re not out there on your own figuring this out as you go. You have a process, you have a thing. On the other hand, if all of a sudden you have like ten questions that you’re answering all the time, that is a great FAQ resource, that is a great thing that you can turn into a lead night, that you can turn it into a master class. You can do all these things. It’s email content, it’s blog content, it’s all of these things that you can share that show. Not only do you know what the heck you’re doing, but it gives you a tool to build that list and show people what you can do for them.


So some examples that I’ll give you is my very first lead magnet was just ten things that I do when I audit websites. It’s just my process that I’m looking through. And then it gave me a way to audit websites. It gave me a form to fill that I could create and it looked super cool and super professional. It gave me a format to follow when I’m doing live website reviews. It gave me something that I could turn into an ebook, which is actually my free ebook right now. You can grab [email protected] checkup. And what that is it is a new, expanded version of the original checklist that I had. Some things have changed, some things are different. But not only am I showing people what to look for, I’m also showing them what they can do to fix it.


And that’s something that I’ve been building really for the last five years, which is just absolutely insane to think about some other things. Every time I speak, I do exactly the wrong thing. I create a brand new resource and then it sits in my drive for a long time till I’m like, oh, I should do something with all of this stuff. So I recently went through and I hired someone to help me get my house in order, so to speak, so I can do all the things. And I was looking at this list of things and I had well over 20 resources that I’ve created over the last five years.


Some of them have repurposed, some of them I need to do some additional sequoia massaging to, but for the most part it’s this really hyper powerful vault library that I can offer to people that are in my membership that I’m coaching. It’s like, hey, you get access to this, just take it, live with it, love it. Or they can buy them one by one eventually and I’ll be sharing more about that in public as I start developing it once I have some takeaways. So take the leap, build your network, pay for coaching, build an email list, turn everything you do into a resource and really do try to build it in public. But that’s challenging. Number six, focus on process. It’s very similar in many ways to turning what you do into a resource and sharing it.


But instead I bake process into everything I do. So I use some apps to help me automate things like sending a proposal, sending a contract, sending an invoice so I don’t have to stay on top of that stuff. It sends reminder emails when invoices are due. It sends all of this stuff out there, which can be really helpful. On the flip side of that, I took that process and I created a framework and now people know what they’re getting. I can say you are here. When we’re working together, they have our roadmap for what our project is going to look like, in part because it’s so heavily process driven.


Not only does it make me look super cool, it keeps me organized and it makes sure that I’m following through on all the things, but it also has some really powerful benefits for other people. So as you build your process, focus on the steps, focus on why you do them for you, and then look at some potential benefits for your audience. And talk to them. Talk to them, because if they may tell you other things that they found super beneficial about your process that you didn’t even consider talking to. People really should be on this list. So I’m going to add an 8th at the end here. But number seven is when you are first starting out, particularly if you’re starting out like I did, because you needed something and job wasn’t working for whatever reason.


Like I had two small kids at home, it was very hard for me to find a job that gave me the flexibility to be with them because it was just me at home for a long time and also paid enough that covered childcare. So instead I opened a business and I said, okay, I don’t have childcare as an expense. This is good. But what I didn’t realize is what the cost of running a business was. So that’s takeaway number seven, charge more.


Running a business costs more than you think because you have at least a quarter of it going to taxes, and then you have all of the overhead that you own, your computer, your software, if you have an assistant that you need to hire, if you have to pay for any app subscriptions, and you’re going to have to pay for some, you’re going to have to pay for coaching. Charge more so you can cover those expenses so you’re not scrambling from paycheck to paycheck, because that’s the last thing you want. You want to make sure that you have this nice little bank built up so that when there’s some slowdowns, you’re covered. And keep in mind that even if it feels so damn easy to you that you can’t believe someone would pay you for it, trust me, it does not come easily to everyone.


And that’s a really hard mindset thing. There’s inherent value in it. There’s inherent value in what you can bring. And first of all, your value is not tied to what you charge, but more importantly, what the value that you give to someone else, even if it’s easy for you can do it in your sleep. They may struggle over that. And so that there’s value there. Okay, number eight is talk to people. And I’m not just talking about talking to people in your network where I said, build colleague list. Build potential client lists. Talk to your clients, find out what they like, find out what their pain points are. Do your market research. Figure out what the heck value you bring to other people.


And I just talked about, like, you may not be able to believe what that value is because it may not come naturally to them. But on the flip side, by talking to them, you’ll learn what that is. For example, what you do and what you think you do may not be the same as what your clients think you do or your prospects think you do. They just want to solve a problem, right? They want to solve a problem, and they want someone to solve it for them. But what that problem is and how you talk about it, they may not realize that what you do offers that solution. So if someone’s like, gosh, there’s a disconnect. Things just aren’t clicking. What’s going on? It’s probably brand messaging, or it’s very likely brand messaging, but they’re not going like, oh, I need brand messaging.


They might be like, do we even know our audience? What is it that they need? What is it that they want? And then we’re going round and it’s like, oh, yeah, it’s brand messaging. But they may not realize it. So all that to say that by talking to people, you can uncover what that is. You can find out what they like about you. You can find out what your opportunities to improve are. All of these things can make you a stronger business owner. There’s so much more I could talk about. Clearly, I have far more than seven or eight takeaways, but I probably need to stop because I could keep going on this. So this will go on the blog. This will go on YouTube. If you have any questions along the way, hit me up. If you want to know.


If you want to talk brand messaging, let’s 100% do that. If you want to talk website copy, let’s 100% do that. If you want to explore what working together could look like to help you hop over those lumps and process and kind of move past them more quickly, talk to me. We’re launching a beta offer very soon, so that’s going to be fun. Finally, if you want to learn more about some of the pitfalls of running a business, particularly as a copywriter writer, really, for anyone going into the online business space, some friends and I just launched a podcast. It’s called the coffee table. And we go into all of this, some of the pitfalls we see, and we’ll have lots of interviews over.


The next interviews will start in the fall, but we’ll have lots of interviews coming up where you can hear from other people, not just the three of us, so you can find that [email protected]. All right, any questions? Hit me up, dms. All the things I look forward to this, and this has been a really exciting time in my business. Looking back over the last five years, I’m sure I’ll have more takeaways as we go. But for now, onward network.

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