Whether it's a side hustle or several side hustles making up a full time hustle, more and more of us are freelancing our way to freedom or at least dipping a toe in the gig economy

While life as a free agent can be liberating and exciting, it can also be tough to navigate and there are plenty of potential pitfalls along the way. I've been a full-time freelancer for 12 years now, writing and working while raising a family and traveling or living on five different continents along the way. 

Over those years I've had plenty of successes and failures, made a fair amount of mistakes and learned some tricks that I think can apply to most trades. So here's six secrets to surviving in the 21st century gig economy:

1. A reality check to kick this list off: Unless you have already accumulated all the wealth you and your family will need for the rest of your lives, there is no such thing as true independence. Almost no one gets to wake up and do whatever they want all day and be assured that someone will pay them for whatever that is. We are all accountable to a client or an audience or a market that is willing to compensate us for the value we can provide. This all might seem obvious, but many people hear the word 'freelancing' and have visions of freedom, and the independent lifestyle does provide that, but that doesn't mean it's a total free-for-all. It's important to always remain realistic. 

2. With that bitter pill out of the way, the amount of independence that comes with being self-employed really can be pretty great. However, a best practice that many people overlook is keeping your enviable situation to yourself as much as possible. The last thing your client wants to see when they're waiting on your overdue assignment is photos of you windsurfing off some gorgeous beach. This is particularly hard in the era of social media, but be careful not to be too gratuitous oversharing your latest travels or other experiences afforded you by the lack of a nine-to-five grind in your life. Trust me, your clients don't need and don't really want to know how great your life is.

3. Work like you're on vacation. This is something we should all practice that I've written about at length here. In an nutshell, vacation work mode requires minimizing distractions, getting your priorities straight, compartmentalizing and being ready for anything. 

4. It's going to take longer than you think. By now you've probably noticed that you tend to overestimate the amount you can get done in a day, or you underestimate how long most things will take. This isn't always the case of course, but as a human who speaks to other humans, my life-long unscientific study of what I call optimistic productivity estimation has found that we all do this, like, a lot. Guard against this instinct and plan for the worst instead, especially when setting up timelines with clients. This leads nicely into my next secret, which is to ALWAYS, ALWAYS...

5.  ... Under Promise and Over Deliver. That's UPOD, for short. It's a business cliche, but it's doubly important for independents, because it will allow you to achieve another important secret to gigging success, namely...

6. Nailing down steady work and repeat clients. Yes, yes, I know. This is starting to sound a lot like the rat race kind of work you were trying to escape via freelancing. Working steadily for the same people seems more like a full-time job, right? Please re-read item number one on this list before continuing. Welcome back. Now remember that always courting new clients means lots more time spent pitching and prospecting and basically working unbillable hours. It's exhausting and essentially unpaid work. Repeat business is always good business, especially for a freelancer. 

There you have it, six of the secrets that I really wish someone had shared with me around 2006.

Keeping all the above in mind might not guarantee your success as a freelancer, but I can guarantee it will make the journey a lot less painful. 

Published on: Jul 18, 2018
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