7 Tips for Transitioning from Day Job to Freelancer or Entrepreneur

August 12, 2014

This afternoon I had coffee with a guy who wants to leave his day job to work freelance.

He asked all the right questions — how to know when it’s time to make the leap, what he should do to prepare, whether it’s the right decision. And while I have my answers right here in my head, I figured I’d get them on paper the blog to share with you.

While I no longer consider myself a freelancer — this post explains why — I did start out that way, and the hustle is still a big part of my business. Whether you want to make a living as a freelance writer or start a custom carpentry business, it makes sense to set yourself up for success while you still have the security of your day job (if you can).

With that in mind, here are the most important pieces of advice I shared today:

1. Figure out the financial stuff

This is one of the biggest factors that keeps go-getters from taking advantage of the new world of work, and rightly so. (It’s so big that I’m working on an ebook on the topic!)

But while it feels like a huge, daunting obstacle, the truth is that you can break it down into manageable bits. Figure out just how much you spend each month, so you know how much money you need to make to avoid dipping into your savings or going into debt. You can always earn more later — and you will — but this is your baseline.

Then make a plan for how you’ll bring in enough work to hit that baseline revenue, and start doing it. These two posts offer more advice about the financial side of working for yourself.

2. Land a core client

Do this while you’re still in your day job, because this is the client that will help you make a change that will actually last.

A core client — that’s my own term, so if you haven’t heard it before, don’t feel like you’re behind on freelancing lingo — is someone who pays you a retainer month after month, a paycheck you can depend on. Once you have a core client under your belt, you can cobble together the rest of your income. Even a small bit of stable revenue makes that possible.

3. Make networking a priority

Start now. It will take a while to grow the type of network you’ll need to develop a stable of clients, and the more of a headstart you can give yourself, the better.

Be strategic in your networking, so you have both a community of people who will support you when you leave your job and a whole lot of warm contacts who might want to hire you (or know someone who might want to hire you).

4. Beef up your online presence

Create a website that shows why people should hire you (here are some examples of portfolio sites from The Write Life), and get active on social media. Do this while you’re still at your day job, so you’re already well on your way to an awesome online community when you really need it.

If you do this well, you will never have to look for work. Instead, clients will find you. This is the sole reason my Socialexis team has never had to look for clients: we always have a steady stream of inquiries. Having an impressive online presence that demonstrates both your work and your network is the best possible form of inbound marketing.

5. Develop your elevator pitch

Figure out exactly what you’ll offer, and be able to explain that offering to anyone who asks. Also make what you offer clear on your website. Even if you offer a bunch of different services, nail down your main service and work the others in around that. No one will hire you if they don’t understand or can’t remember exactly how you can help them.

Image: How you present yourself

6. Max out on work

Before you make the jump, there will be a tipping point — and you’ll feel it. You should be pushing as hard as you can on your side gig, working mornings and/or evenings and/or weekends, while still working your full-time job — until you can’t push anymore.

This is not easy, of course, which is why only true go-getters get through it. Max out for as long as you can without burning out, until you have the other pieces (see above) in place. That’s when it’s time to take the plunge.

7. Leap before you’re ready

Don’t jump the gun; you want to set a solid foundation before making the transition, so you’re more likely to succeed on the other side. But you’ll never feel fully ready, and eventually you’ll have to push yourself to pull the trigger.

Self-employment isn’t for everybody — you have to be highly self-motivated and able to deal mentally with the uncertainty of an inconsistent income. But if you can get past those two obstacles, being your own boss is amazing. It sets you up for more autonomy, creativity and income than you’ve likely seen before. At first it will feel terrifying, and then…


What other advice would you give to someone who’s thinking about leaving their job to become self-employed?

P.S. I also have an ebook on this topic: Turn Your Side Hustle Into a Full-Time Business. It’s geared toward go-getters in the digital world, with a focus on building your email list, selling ebooks and ramping up revenue.

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    10 Replies to “7 Tips for Transitioning from Day Job to Freelancer or Entrepreneur”

    • constance says:

      You should never leave your work just to become a freelancer if you’ve never freelance before. People have this crazy idea that freelancing is easy only to regret it afterwards

    • Krystal says:

      I *just* experienced #6! I was pushing myself hard to work in the mornings, nights, and all through the weekends. Once I had lined up enough work, I was able to leave my 9-5 grind with no worries. It was SO worth it!

    • Antara Man says:

      I plan to quit my dead-end-job to become a full time fictional writer yet I intend to try pitching articles on sites where they pay for guest blogging. Being a self-published author doesn’t require a core clients as by freelancing but at least 1000 true fans. Yet being an entrepreneur takes you to have the guts, jump into the experience when you intuition tells you: “now!”.
      As Steve Scott says: “Take action, get results”.

    • Matt says:

      These are awesome tips. Sometimes you can feel trapped, but you never are if you’re willing to put in the work to get where you want to be!

    • Courtney says:

      Alexis – These are some of the best and most realistic tips for success that I’ve seen. A lot of motivational ‘quit your job’ content is so focused on just taking the leap that I think we sometimes forget that there are some very foundational things (i.e. FINANCES) we can do to better prepare ourselves for success once we jump. Thank you for breaking it down!

      I also think that we all are in very different situations and can take on more or less risk as a result, and that’s perfectly okay. It’s not a one-size fits all kind of thing. As a 30-something who’s married and has two kiddos, I find myself more focused on financial security than someone who may be right out of school, for example. As a solution, my husband and I reviewed our options and set specific financial goals which we revisit every 2 weeks while I ‘side hustle.’ We’re close to achieving our goal and both feel like we’re on a path and not lost in the sea of mediocrity.

    • Susan Shain says:

      Awesome advice! Love how you broke it down step-by-step. I’ll definitely be passing this on to anyone who asks about leaving their day job!

    • Hi, Lexi!

      Awesome article! I’m way more of a risk-taker — and was more fortunate in many ways — than most folks who choose to make this transition, but if I had a do-over, I’d follow your advice. At least some of it :-). And as a result, I’d probably save myself a lot of the grief I’m currently going through.

      Just wanted you to know I curated this for my own blog, quityourjobandthrive.blogspot.com. Thanks so much for taking the time to share your thoughts with that lucky guy at the coffee shop — and with us!

    • Becks says:

      Hi Alexis
      I have been following your blog and enjoy your advice as it is so down-to-earth and relevant to me. I have felt overwhelmed with other experts who confuse me with jargon and tech-speak!
      Number 6 is tricky for me as Im trying to balance family life with part-time work and writing a travel blog in France but your posts give me motivation and have helped me immensely at seeing the big picture.
      Thanks for the inspiration and advice

    • With hard work, perseverance and a good financial life line in reserve it a person may be able to make the transition. It will take discipline, but it can be done.

    • Thomas James says:

      A must read for all who aspires to be a writer. This is a good jump start for all, thanks for sharing this.

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