How to Transition from a 9–5 to Self-Employment

Gillian Sisley

Here are the 4 necessary steps to turn your dream into reality.

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Now that I’m self-employed, I can’t imagine working for someone else ever again.

In fact, the prospect of that is basically my worst nightmare.

I remember what it was like sitting in that cubicle wondering if that was all my career was going to be.

I vividly recall that dreaded, sinking feeling inside as I considered how unfulfilling my work might be for the next 40 years, until retirement.

The prospect of that was utterly terrifying.

Here’s the truth — life is too short to spend a majority of your working hours doing something you hate.

And so, because I couldn’t find work that fulfilled me in any job description, I sought to create my own work through self-employment.

If you’re feeling the same dread I describe above in your current 9–5, I want to see you achieve the same fulfillment I have in my work for yourself.

People ask me often what it takes to transition from their current full-time job to a self-employed lifestyle — in fact, my husband is currently in the midst of this very journey.

And so, considering the best advice I can offer him, here’s what it takes to make that dream of leaping into your own hustle a reality:

Step 1: Do your research and be flexible.

Research is the first and most important step for every and any business. This is when you make your discoveries and find out key information to facilitate your leap to entrepreneurship.

You have to make sure there’s a demand for the service or product you’re offering. If there’s no one to purchase it, then you can’t make money off of it.

From there, once you’ve gotten to know your target audience, you’ve got to start plotting your niche. Based on the interests of your audience and what is actually marketable, you’ll need to be flexible in how you offer your service or product, and what you offer based on the needs of the market.

What you think is best or what you like most doesn’t matter — you’re selling to your target audience, not yourself. It’s about what THEY like.

Having flexibility top-of-mind is what’s going to help you survive as you build your business. You need to be able to adapt and change different pieces of your offering along the way.

This tweaking and refining is a necessary and unavoidable part of the process.

If you’re not willing to be flexible and adjust your course of action at any given time, you’re going to be exponentially extending the timeline of making your business profitable.

And to be frank, if you’re really unwilling to be flexible and adaptable, you may never see your business become a success.

Step 2: Be willing to make the necessary sacrifices.

This is something you need to be really honest with yourself about.

Take some time to ask yourself the really realistic questions of how far you’re willing to go and what you’re willing to do to make your business succeed.

Are you willing to put every spare dollar into funding your startup? Are you willing to pass up hangouts with friends and family so that you can focus on your work? Are you willing to tough it out for far longer than you’re expecting? And are you prepared to put in a hundred times more work and effort than you think it will take?

These are the realities of building a business while maintaining full-time job.

Be prepared to sacrifice a lot of your free time to make this dream a reality. Your evenings, weekends, and any spare 10 minutes will need to be allotted to building your business or dream.

If these sacrifices seem too great, or you’re not willing to make them because you don’t think you’re up for it, then frankly you may not have but it takes to create and maintain your own business.

That’s just the honest truth.

Step 3: Make sure you absolutely love your service or offering.

I always tell people that the best side-business is something you would do in your spare time anyway, because it’s something you’re extremely passionate about.

When I chose to start my social media business while I was still in school, I was spending a lot of spare hours in the week researching social media strategy and marketing, because it was something I was really interested in at the time.

Here’s another example — writing has always been my biggest passion, for as long as I can remember. So, building my career in creative writing made perfect sense when I was looking for ways to diversify my income streams beyond just social media marketing.

If you’re in this just to make some quick cash, you’re in for a rude awakening.

There’s next to no quick cash involved in this process.

There are going to be a lot of days when the only thing that’s fuelling you and getting you to keep moving forward is your passion and love for what you’re doing. I can assure you that the money is not going to be flowing in anytime soon.

But that’s what it takes. You’ve got to build your brand, build your commodity, and put in that investment to grow your service or offering into something substantial enough that people would actually be willing to pay money for it.

And if you don’t love what you do, or you’re only in it for the money, you won’t be likely to last beyond a few months.

You’ll need to last a lot longer than that if you want to see your business become profitable. Which brings me to my final point:

Step 4: Settle in for the long game.

This transition is not going to be quick. If it was easy, everyone would be doing it.

In an ideal world, people who are aspiring to be self-employed hope that with enough hard work and dedication they’ll be able to make their hustle profitable within 2–3, maybe 4, months.

But I am here to give you a reality check — it’s going to take a hell of a lot longer than that.

From the time I started my social media business, it took 7 months to reach anything close to a full-time income. Mind you, I was fresh out of school and was hopping around with a few part-time contracts, but didn’t have full-time employment yet. So that was 7 months of putting full-time hours into a business, through client work and networking and business strategy and everything in between, before I was able to make a full-time business from it.

And as far as creative writing is concerned, I only just recently reached the equivalent of a full-time income through my writing. I’ve been trying to make that reality happen for 3 years, between writing young adult fiction, publishing personal essays online, and everything in between. 3 years of actively trying to build this brand on the side of running my social media company.

Are you willing to stick with it for years? Because it might take that long, or it might take even longer.

It’s the ones who become discouraged and give up who never make it a reality.

I sincerely believe that if someone can be flexible and stick it out, they’ll find a way to make it happen for themselves.

But I can promise it’s not going to be an easy journey.

Final word.

I hope my advice and insights in this article have been helpful for you.

I completely understand and recognize the anticipation, urgency and desire to just be able to walk and work oh, quit your job, and start running your own business full time.

I see that aching and my husband every day these days listen tirelessly work towards being able to break free from his 9-5 job.

I remember exactly how painful and anxious the time was as I desperately trying to make my social media business profitable.

That said, be wary of that desperation. I know for a fact that when business owners get desperate, they start making mistakes.

Have faith that your day will come, and in the end all of your hard work and patience will pay off.

Keep your head on straight, keep showing up to do the work every day, and you will see fruition come from your efforts.

You’ll get there.

I have no doubt.

Just stick with it and you’ll find a way to make it happen for yourself.

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