From Employee to Business Owner: How I Overcame My Biggest Business Challenge

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Are you in the process of transitioning from employee to business owner? Here are the 3 things I did to make this transition success and how I overcame my biggest business roadblocks.

Today I’m opening up about one of my biggest business struggles and sharing how I overcame it. This idea is inspired by the Office Depot Business Solutions Center, and is part of a sponsored series I’m doing with Office Depot via Socialstars. Join the conversation on social media using the hashtag #GearLove.

Quitting your job to work for yourself is one of the most exciting, and rewarding things you’ll ever experience. When I finally quit my steady day job to launch an online business, there were lots of little obstacles along the way.

From paying my own taxes, to being productive while traveling, to outsourcing work, to invoicing and following up with clients, I had a lot to learn. But one of the biggest challenges I faced was not running my business like a boss, and that mistake has cost me dearly.

Struggling with the employee mindset

I worked at my accounting day job for almost 11 years. I was used to having a boss tell me what to do and how to do it, for most of my life. When it came time to quit my job, and dive head first into my freelance business, I struggled with the idea that I no longer had to answer to anyone.

There was no schedule for me to stick to, no 8:30am phone call check-in every morning, no pre-set lunch hour, or monthly budget meetings. I was free! But with this freedom came a lot of uncertainty.

I was so used to asking for permission that I didn’t know how to transition from being an employee to being a leader. So I fell into the trap that most freelancers fall into, and that’s responding like an employee when working with clients.

Instead of thinking like a boss, and working ON our businesses, we get stuck in the cycle of answering to deadlines, trying to keep our clients happy, and working IN the day-to-day minutia of freelancing.

This has cost me a lot of income I could have earned from client projects, as well as big picture ideas that could have led to more success and less headaches. In other words, having an employee mindset cost my business time; time that I can never get back.

I struggled with this for way too long (2 years to be exact), and have only now been able to get past the employee mindset block and learn to be my own boss. If you’re dealing with answering to your clients like mini-bosses, here’s how I overcame this hurdle — and how you can too.

Embracing being the boss

The first step towards becoming a leader is to recognize that you struggle with being a follower. Once you admit that you’re still thinking like an employee, it will be much easier to change your habits and embrace being the boss that want to be.

1. Stop asking, start telling

One of the first mindset shifts I made was to stop asking clients and peers for permission and start telling them what I plan to do. For example, instead of asking a client if I could change our weekly call time, I stated that I would need to change the times and for them to please let me know another day that worked for them (therefore leaving no room for them to argue).

See how framing this from asking to telling puts me in a different mindset? It also lets the client know they can’t reschedule a meeting any time they’d like — I have set boundaries and other projects that have to be completed.

2. Learn from other leader’s examples

Being your own boss, and a leader in your industry, is tough. In the past I’ve cried because I had to let a client or team member go, but I knew it was the right thing to do.

Bosses make decisions that are best for the long-term success of the business, while employees make decisions based on short-term gains.

To find support I reached out to my fellow biz owners and entrepreneurs to learn from their experiences. I read tons of blog posts, (like this post from the Office Depot Business Solutions Center about how to avoid being an indecisive leader), resources, and downloaded several ebooks about becoming the boss.

We grow up with a lot of misconceptions about money, the American Dream, and how our careers and lives should be. But if you truly want to gain the freedom you’re looking for, you have to become a leader.

teach clients quote

3. Take the initiative

In my coaching sessions with other freelance business owners, I’ve found that “taking the initiative” often means asking for forgiveness instead of permission. But in my personal experience that’s not what this phrase means.

Instead of assuming what your boss or client wants, taking the initiative means that you’re listening, watching, and observing them, and then anticipating what they want done next. You’re able to use your skills and out-of-the-box thinking to give them what they want even before they ask for it.

Taking the initiative is what separates a good boss from a great one.

Overcoming any business challenge

Running your own business isn’t easy, and there are plenty of days I want to give up and go back to getting a “regular job”. But one thing that does make the struggle worth it is that fact that I get to have complete control over my life and career.

I no longer have to refer to anyone about what projects I work on, when I take a lunch break, or if I want to nap in the middle of the day. In addition, my potential for income is essentially limitless — the more work I put in, the more reward I get back. This kind of freedom is priceless!

Do you struggle with being the boss? How are you changing your employee mindset to one of being a leader in your industry?


  1. Kirsten says:

    I can’t wait to see how I’ll work through this after Friday (last day at work!)

    The meeting example? I do that now, at my job. I tell people all. the. time to reschedule meetings if they expect me to attend. Will I change the way I operate when I leave the comfortable corporate world, where I have a boss who backs my every move? I sure hope not! I believe I will carry the confidence forward, but I love reading your experiences. They illuminate the path before me.

    • Carrie says:

      Woohoo! Congrats on your last day of work, Kirsten. How exciting. 🙂 I’m glad you were able to be confident and set boundaries at your day job. That will definitely help while you’re making the transition to being your own boss. I don’t think you will have an issue with it since you’re already in that habit mode. Good luck!

  2. Sarah says:

    Great tips Carrie! I feel like this post came at an excellent time for me. It’s Thursday and I feel like I haven’t gotten nearly as much accomplished as I had hoped this week. Thanks for sharing – I think these will help me.

  3. Taylor says:

    So much wisdom from your blog and the Careful Cents group in the last week! A lot of these points are things I’m just starting to overcome now. I could have accomplished a lot more in the last year if I wasn’t in my head so much the whole time. And instead of feeling bad about it I’m trying to push on and learn. Great advice!

  4. Anna says:

    I almost feel like having this kind of struggle makes you a good business owner, because you come at it from many perspectives! Despite people needing to be told what to do, it’s also very important to be fair. Being kind to people has paid off in my business so much. Of course, I was used and abused at times, but the benefits of being generous (even giving some extra free time) mean people appreciate and know you care.

    I come from a bit of a different background. I have a teaching degree but never quite did the full-time thing for too long.. very hard to find teaching work in this city. I did contracts and part-time work. I really didn’t like full-time work. Most jobs begin too early in the day and don’t offer enough flexibility. I almost always looked forward to my contracts being done because I hated doing the Monday – Friday thing. I love what you said about creating your own lunch break or naps 🙂 That’s definitely a perk. I wouldn’t give up my business even to work in a school board at this point, because I love how exciting it is, how much potential for growth, and what a creative process it is.

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