7 Vital Steps to Take Before Becoming Your Own Boss

April 30, 2013 will be my last day at the accounting job I’ve had for over ten years. The closer quitting time gets, the more excited about the next chapter I become.

That’s not to say I’m not scared of the unknown, but since I’ve taken some smart steps to prepare, I’m a lot less fearful — and stressed out. Oddly enough that’s something I never expected. 

As an A-type personality I like things to be in order and all tied up in a neat little package. Of course life isn’t like that — at all. Life is messy, unpredictable and full of the unknown. The best we can do is create a plan, prepare for any setbacks and keep moving forward.

 If you’re thinking of quitting your job, becoming your own boss, traveling the world or following whatever ambitions you have, here are eight steps to take before making that leap.

1. Hire a Business Coach 

I’ve always been skeptical of hiring a coach — whether it’s a business coach, life coach or any other type. But at the beginning of 2013 I needed a change, and felt like I couldn’t catapult my business alone. 

So I reached out to Steph Gordon, and asked if she’d work with me and my “side-hustle”. Little did I know, towards the end of our sessions my side-hustle would turn into a full-fledged freelance business, and I’d be quitting my day job. 

There’s no way I could accomplish all this — plus all the other things I’ve been working on — without her help, encouragement and perspective. After my experience I HIGHLY recommend finding a coach to help you through your next big career decision. 

2. Finalize Your Decision 

Do you want to only work part-time, one day a week, as a contractor, or do you want to quit your job altogether? 

These are questions I asked myself to make sure I knew what my desires truly were. In the beginning I didn’t want to quit my job entirely, but my boss wasn’t flexible or understanding so it made my situation very difficult. 

Eventually it came down to an ultimatum (which I’m pretty sure they didn’t think I would take), and were surprised that I said I had to quit. But now that I’ve come to the end of it all, I’m actually thankful they put me under pressure to finally make that decision. 

3. Launch Your Own Product or Service 

I know a lot of online entrepreneurs suggest this, but I can honestly say it will make your transition to being your own boss that much easier. If you need extra money in any given month, you can promote your own product or service, to make up for any gap in income.

You’ll have more control over what you earn and how you earn it. That’s not something you can say when you have to answer to clients. 

In less than 4 months, I created and launched a group called The Careful Cents Club. Not only does it give me a little bit of recurring income, I’ve made some valuable connections in the event I need to reach out to my network for support, or a new gig. And the street goes both ways for all the members too, so it’s a win-win! 

4. Reach Out to Your Network 

Once you officially decide to quit your job and strike out on your own, one of the smartest things you can do is reach out to your current network of friends, colleagues and existing clients. Let them know that you’re quitting soon, that you’ll have some more time on your hands and are trying to grow your business. 

How will your network keep an eye out for awesome opportunities for you, if you don’t let them know you’re looking? This is a mistake a lot of business owners make — they don’t utilize their current network. 

Don’t forget to reach out and follow-up with existing clients too! Once I did this, I increased my workload (and pay) for several clients while connecting with some very influential people. 

5. Streamline Your Expenses and Test it Out 

I think this step is something everyone starts freaking out about (I know I did!). How are you going to cover all your expenses? Can you really live on the income you make from starting your own business? 

The only way to really know is to readjust your budget (or create one if you haven’t) and start living on the income you currently make from freelancing. Cut your expenses back as much as possible and start saving whatever’s left to help make your leap smoother. 

You’ll notice that it will be a difficult at first, as you and your bank account adjust, but after a few months, it will be much easier. Then once your last of work comes, you’ll be more than prepared to become your own (successful) boss! 

6. Create a Freelance Schedule

There’s very little chance you’ll be able to survive as a solopreneur if you don’t set a schedule and put it into practice. 

Take it from my friend Andrea, who runs her own hosting and design business out of her home office. Often times when she tells her friends or family she’s working that day, they take that to mean they can come over anytime, drop off their kids for her to babysit and basically use her time as they please. 

These days most people don’t understand — or won’t respect — your time when you’re “working at home”. So enforce yourself to live with a schedule and enforce others to answer to your calendar. 

Don’t forget to schedule in time for YOU. My business coach and I call this “self-care” time. You can’t — and shouldn’t — work 24 hours a day, 7 days a week. Why else would you quit so you can have more free time? 

Put yourself and your health, on top of the priority list. This will keep you sane and allow you to actually make money! 

7. Don’t Cheat Yourself

This is definitely the most difficult step out of all the rest — at least was for me. Once I put these tips into action and had my awesome plan of being my own boss in motion, I wanted to instantly check-out of my day job. 

But that would not only be unfair to my boss, but to myself too. After putting in over a decade of hard work, dedication and discipline, I knew I needed to finish strong!

Don’t cheat yourself out of the last few days at your job. Instead, use it as a testing period, to help guide you as you experiment with living on less income, enforcing a freelance schedule and taking time for self-care. 

If you can use your last few days, or months, as a testing ground, then when the last at your job hits, you’ll be able to take the leap smooth and seamlessly — and set yourself up to succeed!

Did you recently quit your job? Have you taken to the leap to being your own boss? Share another step you took to help you succeed! 

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About the author: Carrie Smith is the financial artist and owner of Careful Cents, a site that helps creative freelancers discover the art of making a living. In May 2013 she quit her full-time accounting job to pursue entrepreneurship and blogging. Since then she’s been featured in sites like The Huffington Post, Glamour Magazine, and Kiplinger Finance. In her spare time she enjoys painting, sketching, and making food with her chef husband. You can connect with her in real time on Twitter or Instagram: @carefulcents.

Comments on this entry are closed.

  • david April 22, 2013, 8:27 am

    Carrie, this was a great read. My brother is interested in launching his own business and I’ll pass this along to him!

    • Carrie Smith April 23, 2013, 7:57 pm

      Thanks David. I hope you and your brother are successful in your businesses going forward. Good luck!

  • Michelle April 22, 2013, 10:20 am

    Love this post. I’m hoping to become my boss sometime soon. Hopefully sooner rather than later!

    • Carrie Smith April 28, 2013, 1:27 pm

      Good luck Michelle!

  • John S @ Frugal Rules April 22, 2013, 11:07 am

    Congrats on being so close to taking the leap! As one who did it nearly a year ago now, I can attest to many of these things. The schedule thing is HUGE as it can be so easy to allow time to get away from you and that time is money. One thing we also did was to go all out in terms of networking and reaching out to new contacts…even if they’re cold contacts. We took boxes of donuts to about 12-15 area ad agencies, along with business cards and posters, our first month. We did not know people at many of them, but got two of our biggest clients by doing so.

    • Carrie Smith April 23, 2013, 7:59 pm

      Wow! That’s a great tip and story John. I’m a big fan of constantly networking and putting yourself out there, so I’ll have to implement your idea. Thanks!

  • Shawn James April 26, 2013, 12:42 am

    Great post. No, recently I am not quit my job but soon I am start own business. I like it your “The Freelancers Club” information that is good. According to me, club membership should be free or 30 days trial period because it’s another way to promote own business online because today networking is key of success or if it’s not possible to you so you can add sign up with facebook button that’s best way.

    • Carrie Smith April 28, 2013, 1:28 pm

      Thanks for the feedback Shawn, you’ve got some good ideas!

  • Jeffrey Trull April 30, 2013, 12:01 pm

    I’ve still been thinking about hiring a business coach (although I’m full-time freelance, not getting ready to quit), I just haven’t found the right one yet. I can definitely see the value a coach would provide in either case.

    Another piece of advice: pick a date to quit on, no matter how off it is. It’ll give you something to work towards instead of putting off the decision forever.

  • BrokeMillennial May 2, 2013, 9:31 am

    Great tips! I’ve been strongly considering the freelance route/starting my own business as of late and these are some really good things to consider. I never would have thought about doing a business coach (mostly due to my frugality), but I may look into it now. Being your own boss seems to be the millennial dream, especially in such an uncertain economy.

    • Carrie Smith July 17, 2013, 3:27 pm

      I never thought hiring a business coach would be worth the money either, but I’ve definitely been proven wrong. If you find a good one, they can do WONDERS for your business (and your life!).