Personal Development

How to Transition into Self Employment

August 2, 2016

I’m Michelle.
A modern maker with a classic approach to design. Ever in search
of beautiful typography and
baked goods.
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In this post, you’ll find practical tips on how to transition into self employment and a look into what you can expect from entrepreneurship.

Self employment is quickly becoming the most coveted position out there. You get to be your own boss, make your own hours, do what you want— what’s not to love?

Unfortunately, to transition into self employment is not as easy as flicking a switch. The financial reality is that if you are employed full-time, it probably means that you need that steady income to support yourself. When you run your own business there’s no ceiling on the money you can generate, but there are also no security or guarantees.

So how can you make this transition happen without living out of your car? Here are some tips on how to make that leap without crashing and burning.

Have you been dreaming of working for yourself, but don’t know how to make it happen when you are employed full time? This article explores practical solutions for transitioning into self employment that don’t involve risking the livelihood of you or your family. // From MichelleHickey.Design

Have a plan

Hating your boss is good ammunition for going off on your own, but it won’t get you very far. It’s not enough to know that you want to quit, you need to know what you will do once you leave.

If you identify as creative, what are your greatest strengths and passions? What can you bring to the table to help others in your own unique way? Check out this Brand Blueprint download to help refine your answers.

Build relationships

This step is underestimated and has the most potential to fast-track your success. So much of your business will be about you, so you need to be able to sell yourself before selling a product.

Begin interacting and connecting with other people in your niche and who are already self employed. Tell them your hopes and dreams, ask for advice, and look for ways that you can genuinely help in elevating their businesses. When it comes time to launch your business, you will have a built-in network of people supporting you.

Where can you find these magical people? Just log onto a computer. Search Facebook Groups, participate in a Twitter Chat, Google to find forums in your niche, or join your local Tuesdays Together chapter. It’s okay that you don’t have your own business yet. We all have to start somewhere, and most entrepreneurs never forget that.

Become an expert

One of the other benefits of making those connections is that you will have your finger on the pulse of what is happening in your industry. It’s super important to stay on the ball regarding trends and the needs of your potential customers. If you go into your business armed with the knowledge of a seasoned professional, you’ll have a greater chance of having the success of one.

Live like nobody else

Here’s where the hard part starts. You need to put the time in to begin developing your business. Unless you have a ton of savings, this means working on nights, weekends, during your lunch break, and whatever free moment you can find.

Instead of taking a coffee break, grab your laptop or a notebook and put 15 minutes of work in your car if you need to. If you call yourself a creative, now is the time to use that talent to find those pockets of time you didn’t know you had.

The sacrifices you make by skipping out on girls’ night, missing your favorite tv show, or the tough ones like asking your partner to step up and take on some of your parenting responsibilities, are all investments in your future and that of your family.

Establish a timeline so everyone in your life will understand that this time of absence for you will only be temporary. There’s a quote from Dave Ramsey that perfectly articulates the importance of making these sacrifices: “If you will live like no one else, later you can live like no one else.”

“If you will live like no one else, later you can live like no one else.” – Dave Ramsey

Think small

Set yourself up for small wins by choosing just a few actionable weekly goals. Don’t offer the world when you are ready to launch your website, product, or service. Choose one thing that you are equally good at and passionate about. Build a strong foundation by offering just one or two superior products or services, and add to your offerings as your audience grows.

This will prevent burnout and show your customers that you are dedicated to what you are selling. Two books really helped me understand the importance of simplicity in business, and I highly suggest reading or listening to one or both of them:

1. The One Thing, by Gary Keller

2. Essentialism, by Greg McKeown

Reach your tipping point

When you start bringing in extra income, it’s going to feel awesome. At thatpoint, it’s tempting to see what you’ve accomplished and think you are ready to do it full time. Instead, I suggest moving into a transitional role, where you have one foot in your business and the other in a place of security.

See if there is the possibility of cutting back on your hours or switching to a part-time position within your company. If not, start looking for another position that offers more flexibility but provides you with a steady income stream.

This may be an eye-opening experience for you. When I got let go from my job in 2009, I started freelancing to supplement my own invitation + stationery business. In that first year, I earned almost double my former full-time salary, working half the hours from freelancing alone.

Use your extra time wisely

At this point, it’s more important than ever to make good use of your time. Pretend like your business is your only source of income, and maximize the potential for earnings in the areas where you are already successful.

If your art prints are flying off your virtual shelves, put the same designs on tee shirts, mugs, etc., and see if you can generate even more income without needing to design something new. Tap into those principles of The One Thing and Essentialism, and don’t waste time on something that’s not directly leading to your main goal of full-time self employment.

Consider the big picture

The period in which you are in this limbo will be different for every individual, and the money you’re generating will not be the only factor in deciding when to go full-time. You also need to consider the amount of money it takes to run your business and your family’s future needs.

You might decide to downgrade and move into a smaller home or a town where the cost of living is lower. Or you perhaps you want to move into a bigger house, or you want to travel abroad for a year and need the extra funds to make that happen. Whatever your situation is, be honest with yourself in knowing when the time is right to complete your transition.

Making the transition into self employment

If and when you reach the point where you are generating enough income to support yourself, it’s time to pull the plug— if you want to. You may find that running your business while working part-time or freelancing is the right fit for you, as it has been for me.

You may also realize that you hate working for yourself and were just in the wrong job. If so, take this time of exploration as a learning experience. When you set off on this journey to transition into self employment, your goal should not be to become self employed, but to find happiness.

It’s easy to be anxious and want everything to fall into place quickly. We live in a world of instant gratification, and it’s frustrating to realize that establishing a fruitful, successful business doesn’t happen with the snap of your fingers.

As you are on your journey and experiencing those moments when you feel like you will never reach the finish line, remember that it’s the ones who keep going that emerge victorious.

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  1. Ina says:

    Hey Michelle,

    Firstly, congratulations on your new endeavours ! Wish you all the best.

    I’ve been inspired by you and your work for the last few months now, since the moment your blog. Thank you for great suggestions, that I found in this article! All is left to do now –> HUSTLE !

    • Michelle says:

      The hustle is real, Ina! I’m working on it every day and I know that you can too. 🙂 Thanks so much for your kind words and for supporting me here + on social media too!

  2. Ann Marie says:

    Great post! Very inspirational and useful information. Thanks for sharing!

  3. Carmia says:

    Congratulations on your new website, Michelle! It looks fantastic and I know it will be a huge success. I can’t wait to learn more from you!

    • Michelle says:

      Thanks so much, Carmia! It always means so much to hear from you, fellow rockstar graphic designer!

  4. Nyle says:

    Great points discussed here, Michelle. One of the biggest difference I experienced was on how I manage my time. I was working from home but employed full time to clients. It made me procrastinate so much that i didn’t realise I wasn’t bringing value anymore.

    When I decided to shift my mind to being a business owner than just being an employee, it made me value my time more and my client’s businesses increasing, so much of my productivity. It enhanced the value that I’m providing to clients. Well, you badly need highly productive hours especially with 3 kids around. You won’t have all day.


    PS It’s been a while that I haven’t been here and I love the new site. It’s sooo pretty it makes me want to eat it. ????

    • Michelle says:

      Thanks so much for your comment, Nyle! Time management is a huge factor, and I’ve experienced some in the same struggles with trying to freelance + run my business at the same time. You have some great insights on productivity and I appreciate you sharing! 🙂


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