Mistakes I’ve Made Running My Own Business

Updated April 2023

Owning a business can feel a bit like an experiment at times. Packaging things up, testing them, refining them, and testing them again. It’s only by going through this process that you can actually know what works and doesn’t for you and your clients. 

With Dakota Design Company being my second business (my first was a wedding and event planning company that I ran from 2007 to 2014 in Arizona and Illinois), I’ve certainly experienced my share of failures, but I’ve always learned from them (even if I needed to grieve and beat myself up for a bit first). 

There are always lessons to be learned in failure. 

Something that I think resonates with my clients is that I am a done-for-you service provider, just like they are. I don’t simply tell them what to do and then check back a month later on their progress. I advise them on what to do and then I also do the work alongside my team to make those things happen.

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After I wrap up a kickoff call with a client, and depending on their implementation plan, my team and I could provide anywhere from 10 to 40 hours per week to that client. GULP!

So, I get what it feels like to juggle client work along with business work. To check your team’s work. To delegate tasks when you’re a control freak. To feel the pressures of client requests along with the big dreams you have for your company. To want to support your team and pay them well and give them good projects. 

I know the feeling of overwhelm when you literally do not have enough physical time to do all the tasks on your to-do list unless you stay up late and wake up early (that’s called “burning the candle at both ends” in case you didn’t know!). 

If I ever make things look easy or fancy, it’s honestly probably an Instagram filter-ha! I have certainly made my fair share of mistakes over the years when launching and running two businesses of my own. 

In this post, I’m sharing a few of the biggest mistakes I’ve made, plus what I learned from each one. If these resonate with you, or if you’re in the midst of one of these mistakes right now, KNOW that there are greener grasses on the other side if you can apply what you’ve learned.


01 | I hired the wrong team members and then kept pushing through because I had invested time and money

You know the saying, “Hire slow, fire fast”? Well, I’ve certainly gone against that a few times in my business, and guess what? It wasn’t a good situation. 

Now, I’ll start by saying I’ve never had a subcontractor or team member do anything illegal (thank goodness) or financially harm my business (at least intentionally). I’ve also never had to terminate anyone without cause or notice. My mistakes were more related to hiring quickly, realizing the fit was not good, but then not releasing them because I felt like I should keep them since I invested time and money on them. 

I got it all backward. 

A coach I worked with a few years back when I was building my team pointed out to me that hiring is my kryptonite. I love to hire. I love having help and support. I love having a capable team I can delegate to without a second thought, a team with autonomy, professionalism, and intrinsic motivation. So naturally, I love to hire because I know what a team member who is a good fit can do for me, my clients, and my business.

However, I've made a few mistakes in hiring over the years, and the biggest one was hiring someone who wasn’t the right fit and then keeping them on for too long — to be honest, this wasn’t good for me OR them!

Of course, it can take a little while for someone to learn the ropes of what you do and how you do it. But when someone falsely misrepresents their skillset, capabilities, and availability, it can go downhill fast. 

I’ve definitely hired a few people who misrepresented their capabilities, only for me to find out very quickly they had lied. I’ve also had people tell me they were comfortable with remote work, only to realize they were not self-motivated or disciplined and needed to be managed in a physical work environment (something I don’t do with my remote team of subcontractors). I’ve had team members who repeated the same mistakes constantly, BUT rather than let them go, I kept them on thinking they’d get better if I spent more time in training, meetings, and feedback sessions. 

No. 

As an online business owner with a remote team, I have learned that my job descriptions must include language about how I give my team autonomy, and I expect them to be able to manage their time and project deadlines with little supervision. They must be able to work productively in a remote environment. They must be communicative and available during my business hours. When I do reference checks, I ask previous bosses and coworkers how the person did with remote work. Did they need to be micromanaged? Were they able to manage multiple deadlines at a time? How were they about communicating?

These are all things that are top priority for me when I hire for my company because I don’t want to spend time micro-managing someone or fixing mistakes.


02 | I prioritized hiring help for my family when I should have hired for my company

Why in the world would I prioritize hiring help for the most important people in the world to me rather than getting help in my business? This is so backward and out of alignment with my whole reason for starting this business in the first place. 

My kids are the number one most important people to me in the world. They are everything. Yet I previously would just as soon hire a nanny or household manager before hiring for my company, even when I had clear tasks I could hand off. 

When that realization hit me, I shifted my focus and hired two people for my company (not for my kids and house). The results were immediately impactful. I was able to achieve much more at work and lessened the pressure of finding childcare for my most precious little ladies.

Don't get me wrong, I still have help for both (my company and my kids and house), but I outsource more for my business now than I do for the care of my children. In fact, that’s how I am able to take summers and December off…because of my team. Not because of my childcare. 

Check out this complimentary resource: How to Identify If You’re Ready to Hire For Your Interior Design Business


03 | I underpriced my services

You have to start somewhere, and sometimes that means hourly billing and testing different fee structures. I am a big proponent of starting with hourly billing within a clearly defined package. What I mean is, “I’ll do x, y, z for you for $xxxx/month, and that includes up to XX hours.''. 

Not “I’ll do anything you want at $X rate, and you control my workload and timelines.”. 

Yeah no. 

Today I am sharing 11 mistakes to avoid and learn from as a creative business owner.

So, back to my first point about testing and failing — you do the same with your pricing when you start out. You have to test it in the market and see what sticks. Then you refine and improve your service, your process, your delivery, and the client experience, and then you increase your price and gain confidence in your billing methods.

Once you start getting a mix of yeses and nos, you’ll know you’ve hit a sweet spot. 

The mistake I initially made was basing my pricing more on what I thought someone would willingly pay VERSUS how much time it would take me or the positive impact it would have on their business. I also wasn’t accounting for how long it would take THE CLIENT to tackle the work on their own, a significantly greater cost and time investment than hiring me. 

So I had a period where we lost money on every service we booked. Talk about painful. This is also the downside of booking out my 1:1 services quarterly as we do. If we find out we underpriced, we are already locked into the pricing the client contracted for so we can’t make adjustments. This means I have to be very thorough when I price my services. 

When you’re underpricing your services, you also have to take on more clients to meet your financial goals. Which results in being overworked and overwhelmed. Which results in a lesser experience for your clients and more burnout for you. It’s a negative cycle that is hard to break free from. 

Another realization I made when I was underpricing my services was that some clients didn’t take the service as seriously as those who paid more. Which meant they didn’t get as good a result as the clients who paid more. Isn’t that interesting?  

Now I know that pricing is marketing and that higher-priced services get people better results because the client is more invested. We do the math on every service based on the amount of time that goes into each client (from that first inquiry call all the way to offboarding) and we know what the number needs to be in order to be profitable. 

The fewer clients I have, the better we can support them.

The fewer clients we have, the more balance my team and I have in our workloads.

Everyone wins. 

Read this article on why you should not and CANNOT charge your worth like most “business coaches” will tell you.


04 | I overbooked my calendar with clients

I know you can resonate with this one. There were a few times I was so excited to work with a client that I made an exception to start their project when I was already fully booked. 

I also previously booked my client load based on the capacity of the team members I had hired in #1, and that went south when it turned out they could not do the work I hired them for and needed way more managing than I was able to provide (as a subcontractor, they should not need to be managed or trained to do their work — they should come to the table with the skillset already, only needing to learn how your company does things and how you work). 

Anytime I have overbooked or squeezed clients in, my team and I either made more mistakes because we were too busy OR I ended up burning myself out because I truly didn’t have the time. 

The people who pay the price when I do this?

My children. 

Seriously. 

Why would I do that to them?

Again, it is completely against everything important to me. 

It also means when I’m overbooked, I don’t get to work out. 

And health is so important to me. 

I lost both my parents at a young age. I do not want my kids to go through that. 

Working out, managing my stress, eating healthfully, and sleeping well are critical. But when I’m overbooked, my personal health and wellness get pushed to the side. Not to mention the fact that while our services don’t suffer, our client experience does, and that’s EVERYTHING.

That’s why we only book one client at a time, and we take one week off from new clients per month so we can regroup, provide the level of support our existing clients deserve, and manage the internal Dakota projects that keep the company moving forward.


05 | I put clients in control of the outcome

Just as you designers know, the second a client starts shopping, pulling selections, and drawing floor plans, the whole design is about to go off the rails. 

But when you can control the experience and the outcome, the client is always more satisfied and gets a better result (I mean, you are the expert, after all).

Years back, I offered a service that included consulting + implementation hours, and the client could use the hours however they wanted. I didn’t have set outcomes and actually wanted it to be really flexible for our clients. But what happened is the clients used their implementation time for VA tasks, and my team and I knew these weren’t the tasks that would make a major impact on their businesses. It was also hard to manage the flow of work when our clients were in control of the outcome. So yeah, we stopped offering that service. 

This is also why I don’t offer standalone 1:1 coaching or one-off 1:1 consulting sessions without a VERY specific topic. If a client doesn’t ask the right questions or wants to focus on something that isn’t actually the problem, it’s very hard for me to get them a good result.

We now offer a service that is just consulting, but it is very focused on a single outcome: the client experience. It also follows the framework and process we use with our implementation clients, so I am able to control the experience and outcome much better than if it were open-ended and client-controlled.


06 | I said yes to things because I knew how to do them

As an operations consultant and two-time business owner, I have done many things on my own. I can build and design websites, set up all sorts of tech, hire employees and subcontractors, handle bookkeeping and accounting, do SEO, write copy, do content marketing, write email sequences, launch passive products, build funnels, apply for trademarks, read and negotiate legal contracts, etc. 

So, as with the previous point, because I know how to do all these different things, I would often find myself saying yes to client requests, even when I knew they weren't of high value to the client or within my area of expertise. 

Anytime I stray from the client experience focus or send a random request to my team, they always say: “Katie, is this really the best use of our time?”.

PS: Thank you to my team for keeping me focused on the area of expertise that produces the best results for our clients. 

So, while we’ve tested different service offerings and scopes in my business, we know what high-value tasks get results for our clients, and we focus on offering those. When we receive client requests for work that is outside of our wheelhouse, I have no problem turning it down or helping the client to hire someone who can do those things.

Lesson #1: Identify what you do best and what gets the client the best result. Then only do that. If other parts are still helpful but not within your area of expertise, hire someone and then delegate those tasks, so your client gets the complete experience.  

Lesson #2: If you continue to get the same request often enough, it may be an opportunity to offer a new service that would benefit your clients and be a natural extension of what you are already doing (see how we now offer CRM setups?). OR, it might provide insight into a complimentary resource or passive income product that your clients would love.


07 | I took "connect” calls with people who did similar work only to have them steal my stuff 

I am very passionate about the work I do in my business and am a giver (if you’ve read my blog, attended one of my happy hours, or downloaded one of my free resources, you know I give generously). I love to help people, and I have also learned as someone who is a natural people-pleaser and giver, that when I volunteer my time, do coffee chats, or allocate my time and energy toward mentorship and building up others in the field, there has to be an equal energy exchange

Too often, competitors misrepresent themselves when really they are trying to learn from you so they can compete with you. I can count at least five specific times when this happened to me and it’s not a good feeling. It would be one thing if these people had been transparent about their motives, but that hasn’t been my experience. 

What I’ve learned through this is how important it is to protect my time and energy because I can't help myself from giving generously. Knowing that about myself means I have to say no a lot.

On the flip side, I have enough free resources on my website and social media outlets that anyone can learn plenty from me…free of charge. And, unfortunately in the online space, there are tons of copycats who steal your stuff without reaching out to you (but you find out when a client tells you, when it comes up in a plagiarism check, or when you see your stuff being regurgitated across the internet. GRRRR.).

I have also seen that when I can connect with people and do it on a larger scale, like when I’ve collaborated with people who introduce me to their audiences (like my conversations with Luann Nigara here and here, Wingnut Social here, SideDoor University here, Home Designer Marketing here, here, and here, Design Biz Survival Guide here, or my Year End Playbook collab here), there is an equal energy exchange.

Long story short: I turn down requests for my time when there is not an equal energy exchange. But, I am happy to provide information and resources for free when they serve my business and the industry at a larger scale than 1:1 requests (meaning my time spent once is highly leverageable over and over again).

PS: this also applies to paid opportunities as well. If something isn’t a good fit, I turn it down.

Saying NO is a muscle you have to continually exercise in order to make it stronger and easier to do. 


08 | I said yes to clients I knew weren’t a good fit

Today I am sharing 11 mistakes to avoid and learn from as a creative business owner.

We’ve all been there. We say yes to a client even though all the signs are red and our gut is telling us no. But we say yes because we feel guilty or obligated, or as if we’re somehow responsible for helping them, even though that is one million percent not true at all. 

I have done this a few times in my two businesses and I will say, while it’s not fun, it certainly is a very quick way to find out exactly what you will and won’t do for a client. This in turn helps you to fine-tune your marketing and better screen your prospects right out of the gate. 

No better lesson than a bad fit client!

I know that saying yes to clients who aren’t a good fit isn't just bad for me and my team, it’s also bad for the client. 

And that can harm my reputation — because I simply cannot get a result for a client who doesn’t use the materials or software we design and set up for them, implement any of the changes we helped them refine, or enforce any of the boundaries we helped them to establish. 

No one wins in this situation and I find it best to be transparent right from the start. As a team, we have learned exactly what our non-negotiables are, which helps us to ensure our clients and our services are well aligned. Everyone wins!

I will say, kissing a few frogs is par for the course when owning a business. And certainly, as companies continue to evolve, they may kiss a few frogs along the way as they are refining their offers, marketing to a new audience, etc. But just don’t continue kissing frogs over the long haul!


09 | I moved outside of my process and contract

You know I always say “A client who can’t follow your process is always going to be more difficult than a client who doesn’t have the budget.”

I have moved outside of my process “just this once” for a few clients and always regretted it. Outward to the client, nothing was wrong, but internally, it created a lot of inefficiencies and confusion and we weren’t as on top of our communications as we normally are. Why?

Because we stepped outside of our well-documented and defined process that clearly states who does what and when. 

The service itself didn’t suffer, but the client’s experience did.

Part of what is helpful for my clients is to see a business owner who sticks to her process and has well-defined boundaries. In fact, I have had many clients share in their feedback to us that they loved experiencing my process and seeing how it felt to be on the receiving end of a service with such clear boundaries. 

I have learned that staying within our process and being firm with our contract is always best for our clients and my team. And if one of them isn’t happy…then what in the world am I doing all this for!!??


10 | I didn’t follow the green lights

Okay, stay with me here. This is about as woo-woo as I get. I am someone who likes to take quick action and have no problem working hard to achieve what I want. I think the whole “anti-hustle culture” is kind of wrong, because you actually do have to put in the time and energy to create something of value that is going to do all the things you want it to do for you. And there is nothing wrong with working hard. I enjoy working. It exercises my brain and my natural talents, allows me to support and provide for my team and family, and lets me help business owners run better businesses, and connect with amazing women all across the world. There is nothing wrong with that

BUT, I have definitely spent a lot of time deliberating on things and “forcing” things when I should have just followed the green lights — the signs that were already saying YES THIS IS THE THING THAT’S WORKING. 

Now, no one will have only green lights….and sometimes there will be a lot of green lights and you have to decide which one to go after. But if you’re constantly pushing and pushing and it feels like an uphill battle and as if something is wrong, there is a HIGH chance there is. 

I am still learning this (and will continue to learn this every day) but I'm starting to pay attention to the green lights more and more, and less to the red. 

The question “What would this look like if it were easy?” is also a good filter to run a lot of things through. 

And, this is also one of my favorite things about the work I do with my clients. Because I don’t believe there is one single approach to running an interior design business, with every client, we dig into what they like and don’t like, what’s working and what's not. Then I am able to help them see the green lights and then all of sudden things feel easier for them. When they stop focusing on the red lights and move their attention to the green lights, they’re like, wait, why does this feel easier?

Like the designers who offer full service but aren’t comfortable on construction sites. Or the designers who think they have to sell furniture even though they hate ordering. Or the designers who feel they have to source trade and do flat fee when they’re just starting. You get the idea.


11 | I hired business coaches who didn’t have specific experience with done-for-you service providers (OR KIDS)

I’ve worked with a few business coaches over the years and at times felt let down by the level of coaching I received as it related to being a service provider. It seems like most coaches coach coaches these days (say that ten times!), or they only had experience with their one single business, so it’s difficult to find someone who has experience with how to advise an experienced business owner who offers done-for-you services. 

Don’t get me wrong. I still benefited greatly from the coaching and I attribute that to the fact that I am an implementer. If a coach tells me to do something, you better believe by the next session I have done whatever they told me to do and then some to make sure I take full advantage of their expertise. 

I also worked with a coach during Covid who had no kids and no experience as a service provider so could not relate to what I was going through and offered no accommodations, extensions, or empathy as I tried to juggle my clients, my kids being home, and my intense overwhelm. 

What I’ve learned from this is that when I am seeking coaching:

  1. I will only work with coaches who have kids.

  2. I will only work with coaches who have previously offered done-for-you services and who understand the delicate balance of client work + business work.

  3. I also know that any coach I hire for my business needs to be further ahead than me (duh!) and aligned in integrity. So coaches who tell me how much they make, share income statements, use “girl boss” language, or show the unrealistic side of doing a business (working by the pool - lol - I don’t know about you but I can’t see my computer screen when I’m out in the sun…and for real? If you’re that successful, WHY ARE YOU WORKING BY THE POOL?).

Oh, and I also won’t work with someone who swears in their copy or marketing, who has spelling and grammar errors in their marketing, or who doesn’t practice what they preach (like the marketing person who has terrible marketing, or the email writer who doesn’t have an email list, or the blog writer who doesn’t have a blog…you get the idea).


So in conclusion:

Always be learning.

Always look for the silver lining.

Know you can change your business if it's not working for you. 

By failing and learning quickly, I have been able to make changes to my business so it is more in alignment with my professional and personal goals. It’s a constant work in progress. And taking action, even if it means you might fail, will always give you answers.

If you feel like you’re making any of these mistakes in your business, I’d love to hear where you’re stuck. Be sure to join The Weekly Install and receive strategies and tips for streamlining your business. 

You might also like these posts:

12 Things I Don’t Do In My Business

Things I Learned as a Second-Time Entrepreneur

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