When you start your own business to escape a boss, you actually end up with a lot more bosses.
Until your business outpaces the income you make from your job, don’t quit.
The idea of working with your friends is exciting until you realize that you have to actually work.
Treat every client like your dream client.
Entrepreneurship is not a zero-sum game.

In 2020, we’re lucky that DxM Creative has a great network of clients, mentors and resources that we can pull on when we have questions and ideas. But when we started in 2014, we made a ton of mistakes. We had no idea how to manage client relations, what the heck scope creep was, how to work with other team members, or hire contractors. And because of that, we made a ton of mistakes.

Today I’m going to dig into 5 mistakes I made when starting my business so you can avoid these on your entrepreneurial journey.

Mistake #1: Starting a Business To “Be Your Own Boss”


Now I get it. The whole dream of “being your own boss” is what’s sold to a lot of people to become entrepreneurs. When we think about it, though, this mentality stems out of hating being an employee and taking orders from other people.

Sure, when you run your own business you’re at the top of your organizational chart. But you still have to report to people.

You still have clients, customers, and your own team members who are looking for things from you. They’re all your new boss.

Now, you might not have one sole/direct boss ahead of you, but you’ve still got a lot more bosses now to answer to. So instead of being your own boss, change your perspective to being your own manager.

You’ve got to manage your work. You’ve got to manage your tasks. You’ve got to manage your team members. You still have to be in charge of what’s getting done, when it’s getting done, and who it’s getting done for.

The allure of being “free” makes people forget the cost of being a boss. Being your own boss sounds like a lot of fun, but being your own manager is where the work happens.

Everyone wants to be their own boss, but not everyone wants to be their own manager.

Mistake #2: Quitting My Job Too Soon


Fun fact about me: I had about two dozen retail jobs before getting into this entrpreneurship thing.

I had a bad habit of jumping from job to job to job and quitting them abruptly. I’d leave for a lunch break and not come back or just not come in for a shift at all.

It was a weird time in my life.

Part of this back to back to back to back job quitting came from this insecurity I believed where “real entrepreneurs” didn’t work a job. If I was clocking in and clocking out for someone else then I wasn’t a real entrepreneur.

It took me a long time to realize that being an “entrepreneur” doesn’t mean that you neglect your financial needs or collect thousands in unpaid phone bills.

None of that is true. And if you’ve been sold that lie you need to get it out of your head.

Some of the best entrepreneurs you’ll meet are still working jobs, have a side hustle, or have something going on to fund themselves while they build their business.

If you think back to Maslow’s hierarchy of needs, things like security, housing, and financial stability are on the bottom. In order to move up the pyramid to self-actualization, we need to look after the bottom layers first.

If you’re worried about paying your bills or how you’re gonna eat your next meal, you don’t have much mental capacity available to be creative and manage a business.

When you don’t have money in your pockets you’re also more likely to do anything for a buck. I’ve been in situations where I put up with terrible clients who were asking for the moon while I was paid in peanuts. Taking on these projects led to me resenting the client and ultimately not doing good work. It’s not sustainable. It leaves a bad taste in your mouth and you’re going to hurt the client in the process as well.

Don’t feel bad about having a part time job, whatever that looks like, while you’re building your business.

Mistake #3: Working With My Friends Too Soon


You want to feed the family, get bread with the team, secure the bag with your boys– I get it.

But transitioning from a friendship to a professional working relationship really fast can result in a lot of bruised egos and, potentially, hurt friendships.

Without the proper expectations or roles in place, you’ll have silly fights around things like who’s CEO, who’s COO, how you split money– things that really don’t matter when no one has even heard of your business

Now, my cofounder Ali and I are seven years into our friendship and six years into running DxM together. The reason we’ve been able to stick through it for this long is because we’ve had open communication.

Of course, we’ve had our fights and we’ve buttheads over issues big and small. But understanding the role each of us play on this team helps us have clarity on our responsibilities.

You and your friends need to be honest and transparent about who’s good at what and where you suck. Start with your shared goals.

You’re all working together because you want to work together. But what are you working towards?

Whatever your answer is for this, it’s a good benchmark to come back to when you have fights. When arguments happen, you can all ask yourself– is this fight bringing us closer to our goal? Does this fight matter?

This will help you and your friends understand where each of your strengths are and amplify them, while catching each other at your lows, too.

Mistake #4: Burning Bridges


As you grow as an entrepreneur, you’ll learn very, very quickly how small the world is. If you do a good job with a client, the whole world will hear about it. If you do a bad job with a client, the whole world hear about it.

One of the perks of being an entrepreneur is that you get to pick who do business with. You get to be selective about who you work with and if they align with your values or not. That’s a huge privilege. But for me, when I was younger, I thought that was an excuse to cut out anyone who didn’t work the way I wanted them to work.

So here’s a story that I’ll never forget because it cemented for me how important it is to take care of your bridges, no matter how the relationship ended off. A few years ago, we had a sales rep working for us and they had secured this new prospect who was looking to build an HR training platform online. The sales rep was super excited because this new prospect had actually worked with our very first client. It was a warm prospect. Now the sales rep was celebrating. But as soon as I heard the news, my heart sank.

I knew that when I had worked with this first client I messed up big time. I was really hoping it wouldn’t bite me in the back. But sure enough, a few days later, the prospect came back to us and told us, “hey, we’re not going to be working together at this time.” Even though they didn’t say it, I had a feeling that the prospect had talked to our first client.

I learned a valuable lesson from that day. Treat every client like a dream client. Even if they’re not, know that any client can be the one that introduces you to your dream client.

Mistake #5: Being Afraid of Collaborating


When we started doing web design I didn’t want to talk to any other designers or developers, because I thought, if I tell them what I’m working on or if I get their feedback on this client project, what’s gonna stop them from going ahead and getting this client themselves?

It took me 6 years to realize that great designers just want to do great design. Great marketers just want to do great marketing.

There’s a lot of headaches that come with running a business like invoicing, sales, pitching clients, and organizing a team that great developers, great marketers, etc. don’t want to spend their time on. They just want to do great work in the lane and they do it. This is an advantage for you as an entrepreneur because it gives you the opportunity to organize that team and give them the chance to do great work.

Now, if I knew this way back when in 2014, we would’ve been way ahead of where we are now. When you’re just starting out you have a scarcity mindset. You believe the number of “wins” available in this world is finite.

In reality, there’s many different pots of gold. They’re all very large and they’re all virtually limitless. But as as I’ve gone through the motions and as I started to build a small team of realize that when you’re young and starting out, you think that there’s just one pie, one pot that everyone’s digging from and you’ve got to you’ve got to fight for your scraps.

But that’s not the case. There’s a ton of different pies, a ton of pots, and they’re all virtually bottomless.

Whatever you give, you get in return.


  1. If you want to be your own boss, be prepared to pay the cost.
  2. You can’t build a great business on an empty stomach.
  3. Start working with your friends slowly.
  4. Treat every client like your dream client.
  5. Everyone can win.

You’ll Make a Lot of Mistakes


This post could go on to 101 mistakes that I’ve made. But obviously, you don’t have the time to read that and I don’t have the time to write that.

At the centre of these five mistakes is ego.

Believing that I had to have some sort of “rise from the ashes” story and claim all the glory and success for myself was at the root of all these missteps.

This is wrong. Business is a team sport. There’s this great African proverb that says, “If you want to go fast, go alone. If you want to go far, go together.”

I don’t know about you but I’m here to go far. As your business gets bigger and bigger, you can’t do all of it on your own. You need the cooperation of community partners, team members, clients, and everyone around you to be successful.

I still make mistakes to this day. Some of them are rookie mistakes! Even when you eventually land on the cover of Forbes, you’ll continue to mess up. What’s important, though, is how you is how you accept responsibility for those for those mistakes and how you respond to those mistakes.

Thank You For Reading

If you enjoyed reading this and found it helpful, it’d mean the world to mean if you shared this with a friend.

Would love to hear your thoughts on this topic and chat, too. Tweet me @astawadotca or DM me on Instagram

Talk soon,

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