Starting to freelance without losing your day job

by Travis Bennett, founder of Studio Digita (and Nomad Stack)

Finding a job is tough. Finding a job which inspires you to spring out of bed with a scream “I AM MEGATRON” each morning is almost impossible. That’s why so many people are starting to freelance.

So what can you do? Grind away at your desk for hours on end while dreaming of something better?


You need to start freelancing yourself. That first paycheck feels like you’ve struck gold. You’ve just got to turn the skills you’ve been building all through your career into cash. Cold, hard cash.

But here comes the next big challenge.

  1. How do you know you’ll be able to make it?
  2. How do you know if you’ll actually enjoy it?
  3. How will you keep up with the bills if it all goes wrong?

Now there’s plenty of people who’ll tell you to jump in the deep end. It’s sink or swim. Unfortunately pretty much every new freelancer has plenty of success stories. Everyone seems to win, right?

Wrong. There’s plenty of people who started freelancing and failed.

Freelancers who went home with their tail between their legs to work at another soul-less corporate job. Just months after they posted hundreds of lifestyle pictures on instagram and and endless stream of inspirational quotes.

You don’t hear these stories of failures though.

Today I’m going to talk about how to actually make it work when you’re starting to freelance. My advice?

  1. Don’t quit your day job (yet).
  2. Build freelance income streams.
  3.  …
  4. Profit.

The trick to #3 is hard work. When you’re starting to freelance you’ve got to put the effort in to create new opportunities for yourself. So,

  • Stop stalking your high-school crush on Facebook
  • Skip the silly meme’s and cat videos on YouTube
  • Turn off NetFlix and the endless NCIS reruns

It’s time to get to work.

All freelancing is, is doubling down on a skill you already have and selling it as a service to people. Perhaps you’re a great writer and can churn out funny blog posts for companies. Maybe you’re great on camera and can do promotional videos. You may even have the voice of an angel so you’re in hot demand for voice over’s or audio book readings. Whatever you can do, there’s a market for it.

I’m 100% serious. Dancing jungle videos? Inappropriate unicorns? There’s never been a better time to start making a little extra money online by starting to freelance.

Now let’s just assume you’ve not signed a draconian contract with your boss. So outside of the office you’re all good to start doing a little freelance work. Yes, it will take time away from your cat videos. But as you work with more and more clients, you’ll build a portfolio you can use to start a profitable business.

That’s what I did. I started writing blogs. Then I made a couple of websites for fun. Then I built a couple for clients. I’ve grown this into a digital agency and now work with clients all over the world.

So I’m going to say it again.

If you hustle for a couple of months, start to freelance and get a few clients, you’ve got the makings of a business. This is when you can think about quitting your day job and living a life you’re actually excited about.

Starting to freelance and successfully work for yourself

Here’s a few more bits of advice that’ll help along the way:

Be excellent at customer service

It’s OK to accept any work that comes your way as you’re starting out, so long as you’re able to do a good job. The goal is to create a tribe of happy customers.

Happy clients will sing your praises and send you referral after referral. Plus, they’ll also come to you every time they need more work done. After a while, this will begin to snowball and your freelance career will take off.

Be the best. Like expert-level best.

Some of the best freelancers I know are complete specialists in their niche. They’ve mastered one single thing. Of course, they turn away plenty of “opportunities” but that’s the goal.

They’re able to command far higher rates for the work they actually want to do. Find a niche you can specialize in and start there, so you can get strategic once you’ve got too much work coming in.

Get online and get yourself found.

It’s never been easier to get a website. WordPress, Squarespace, Wix, all offer easy builders you can use to get online. The trick is to showcase your best work and top clients. Oh and a few testimonials never hurt. The trick is to spark an interest, and show you’re a credible freelancer to work with. Even if you’re just getting started.

Nail your pricing strategy, the first time.

This is one of the hardest challenges for a new freelancer. How much do I charge for my time? It’s a critical question. Set your rates too low and you’ll be working for pennies. But without a portfolio you’re not going to be able to charge hundreds of dollars an hour.

Just think about it, and don’t be afraid to negotiate. Many freelancing platforms show an “expected budget” to help guide you. My advice is to be happy with the rate you set. Speaking from experience, good clients are willing to pay good money for good work. You’ve just got to prove you’re able to deliver.

Man up and cold-call prospects.

This is fundamental, and no matter what channel you’ve chosen, you’re going to need to pitch for work. Just do it. Go on Upwork and start bidding on work. Or get a list of local businesses and pick up the phone. Starting to freelance requires you to reach out to potential clients. It’s the only way.

What I’ve found works best is recommendations. If a mutual friend can introduce you to a lead, you’ve got a much higher chance of securing the deal. Online you’ll face much higher competition, but stick with it. If you write pitches for each job (no cutting and pasting) you’ll up your chances of landing a gig.

Learn to give an awesome pitch.

Selling yourself is the key to success. You’ve got to learn how to pitch. And by pitch, I mean you’ve got to be able to convince a customer to hire you. Get them to realize how awesome you are, and that you’ll get the job done.

In my industry, a friendly and casual approach works best. Large projects can take months, and people want to work with teams they actually like. Just make sure you do get down to business and aren’t just being all chummy. Talk about your background, why you’ll do a great job, and walk them through what the process will look like.

Get away from your computer.

Don’t get me wrong, there’s plenty of great freelancing opportunities online. But it’s tough, and competitive. Personal connections have been a goldmine for me, and have led to some of my most profitable jobs.

  • If your co-working space has a networking night. Go.
  • Your alumni’s having a dinner. Go.
  • There’s a local group of entrepreneurs meeting for a drink. Go.

Just get off your computer and go networking. You’ll meet interesting people, and may bump into someone who needs what you’re selling. The key to starting a freelance career is to hustle, be active, and go make some real connections.

On my journey I fully replaced my 9 to 5 income by the third month, and have never looked back. Starting to freelance allows you to find your passion, and turn it into a business you can take anywhere in the world.

The only secret?

You’ve got to work at it. Bang out a value proposition, setup your portfolio and start applying to projects. When you start winning them, the opportunities are endless.


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