How to Survive and Thrive as a Freelancer – Lessons Learned

I hadn’t expected my coffee with a friend to be anything more than a routine meeting with a freelance copywriting client. She was starting a new business, I was going to give that new business a voice. This was run-of-the-mill stuff.

At least, it was until she told me something I really wasn’t prepared for:

“I’m terrified. I’m undisciplined, and even though I’m passionate about what I do, I’m scared that I won’t be disciplined enough to get the work done. I’m scared that everything will go wrong. I don’t think I can do it. “

I looked on, hoping I could get away with a sympathetic smile and the reassurance that everything would be fine and she would be great. My friend didn’t give me that easy way out. Instead, she asked me this:

“How do you do it?

I froze.

I didn’t want to tell her that, even after doing this for years, I still find that freelancing can often be scary, difficult, challenging and terrifying.

I didn’t want to tell her that sometimes in freelancing, as in life, things do sometimes go wrong, and that yes, even now, I still days where my discipline is next to non-existent.

I didn’t want to tell her that, because that’s only half the story.

The truth is, that for every challenge, freelancing presents rewards that are above and beyond anything I experienced in the typical 9-5, that for every moment that is scary, there are dozens more that are exciting, memorable, and magnificent.

So I focussed on that, and I shared with my friend exactly what I’ve learned over the years about how to survive and thrive as a freelancer.

Today, with National Freelancers Day coming up on June 8th, I wanted to take the time to share those very same experiences with you, and offer up the following top tips:

1: Stay Healthy

Stay Healthy as a Freelancer

On the face of it, this might not seem like it has much to do with freelancing, but think about it:

Whatever it is you do, you’re reliant on that body of yours to do it. You need to physically be fit enough to show up every day, and to actually do good work once you do.

Get sick, and you risk taking time off that you hadn’t planned for and can’t afford.

Alternatively, you “gut it out” and show up, only to find that you’re so run down you produce poor quality work.

As we all know, poor quality work equals unhappy clients, and unhappy clients are the last thing any freelancer needs.

Conversely, I’ve found that when I’m eating right, when I get exercise and take care of myself, I am more energetic, more productive, and more creative, all of which leads to better work, happier clients, and ultimately, better gigs.

2: Have a Contingency Plan

fail to plan = plan to fail

Even if you’re as healthy as can be, there are still those times when things go wrong, and when that happens, it pays to be prepared.

A year into my freelance writing career, I found myself being taken to the hospital and staying there for some time. It was there that I learned the hard way about the consequences of failing to plan for an emergency.

I ended up dictating apologetic emails to a friend, who sent them out to my clients explaining the situation and trying to buy me some more time.

Trust me, when you’re sick and in pain in a hospital bed, that’s the last thing you want to be doing, especially when some of those clients understandable need to get someone else to do the job to meet their own deadlines.

Since then, I’ve had a solid plan in place which includes things like:

Keeping an updated record of my current jobs

Similar to the system used by Alison Thompson of The Proof Fairy, this is shared with someone I can rely on in case of an emergency.

Use other freelancers to complete jobs if needed

Honestly, I’d rather take a short-term financial hit than lose a client long-term.

Planning in case of damage to technology or property

I know just what I’ll do if my computer ever breaks or -heaven forbid- my home is destroyed in a fire.

3: Work in the Cloud to Eliminate Risks

Working on Google in The cloud

I’ll admit, I love using cloud applications like Google Docs simply because they’re powerful, easy, and can be accessed anywhere at any time, but they also play heavily into my freelancer’s contingency plan.

If my computer is damaged or stolen, all my work and -importantly- sensitive customer information is well protected. It’s all stored securely in the cloud, away from prying eyes, and ready for me to access it even if I don’t have my computer.

Cloud apps can be used for just about everything. QuickBooks’ invoicing software means I can manage much of my basic business finances anywhere, whilst tools like Canva are great for producing marketing graphics, illustrating blog posts, and more.

4: Use Timers, Rewards, And Whatever it Takes to Stay Disciplined and Distraction-Free

Working on Google in The cloud

Finally, we come back to my the problem of my poor friend which kickstarted this whole thing.

As I write this today, it’s a beautiful, sunny afternoon. The weather is warm, the skies are blue, and all I want to do is to get out on my mountain bike and go enjoy myself for a while.

It would be so easy just to go and do that right now.

I’m my own boss. I can do what I like.

But I also promised myself that I’d get this post finished today so, instead, I’m using mountain biking in the sunshine as a reward.

If I stick with it and get this done, I can treat myself to good bike ride. At other times, I have to use other things as rewards, whether it’s a day off work, a movie, or even a piece of cake.

Having something to look forward to at the end of a piece of work makes getting the work done in the first place that much easier – I’m more inclined to sit down and get it done if I know there’s something fun waiting for me at the end of it.

When that doesn’t work, I use a timer to work in short, productive bursts of 40 minutes at a time. If 40 is proving too much, cut it to 20.

I find this particularly helpful if I’ve got a long day tied to my computer, or if I’m getting so distracted that I’m running off to Facebook every five minutes or ordering things from Amazon when  I should be working.

You don’t even need any particular app to do this, just type “set a timer for 40 minutes” (or 20, or whatever) into Google.

Essential Tools for Freelancers - Google Timer - Chris Skoyles

Finally, I’d also recommend using a great extension for Google Chrome called StayFocusd, which helps keep you on course by blocking access to time wasting websites like Facebook for set periods of time.

Use that, or whatever it takes to stay on track, and see for yourself how freelancing can be an exciting, thoroughly rewarding adventure, rather than the terrifying ordeal it can seem to newcomers like my friend.

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  1. Thanks for this! I’ve been freelancing for about a year but I never thought about getting a “contingency plan” together – i’d better get to it!

  2. Thanks for sharing Chris, a great read. Freelance work can be fraught with challenges sure, but like you say it is the rewards of overcoming those challenges that make it all worth it!

  3. Pingback: Chris Skoyles

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