The ABC’s of Being Your Own Boss

A quick search of ‘digital nomad’ on WordPress or Instagram brings up a pretty picture of an ideal lifestyle: warm beaches (or perfectly snow-capped mountains), wine, exotic coffees, casual-but-cute outfits, and the cherry on top: days off whenever wanted to hike, go to the beach, or otherwise just practice self-care.

It’s something most of us – myself included! – would love to have. And if you’re reading this and have achieved your ideal version of the freelance lifestyle (however that looks for you), congrats! It’s a huge accomplishment, and despite the relaxed look takes a ton of hard work.

But despite all of the webinars and courses available on how to leave the nine-to-five and become your own boss, something that doesn’t really get talked about is staying in the position to be your own boss. On average, 10% of client accounts roll off each year. If you (which is most of us) have bills to pay and need to live off what you earn as a freelancer, and are only making a bit more than your monthly bills (or are paying a lot onto old debt, into building your business, etc.), then you’re never really in a position to be able to lose clients. You can’t get comfortable.

Spoiler alert: I got comfortable.

See, it’s great to have an income goal.

“I need X amount of dollars to be able to do this full-time, plus
an additional Y amount to travel / pay off debt / hire a VA.”

But then once we reach that goal, we get comfortable.

This isn’t a post about the ABC’s to becoming your own boss, rather it’s about the importance of ABC: Always Be Closing (yes that’s a Glengarry Glen Ross reference).

It sounds cheesy or very Wolf of Wall Street-y, which is obviously nothing like the relaxed vibe we’re after. But when we get comfortable with our income and the lifestyle it lets us have, we stop actively looking for more. But what happens when that 10% of clients roll off all at the same time? Will you still be able to pay your bills? Will you get stressed out?

If we learn to always focus on sales, and marketing ourselves, it becomes a part of our regular business routine. A couple hours a week, a new client here and there to help us build the buffer. 

Even if we’re at our capacity, selling and taking sales calls (not necessarily signing new clients) helps keep us on our game for when we suddenly do need that new account. It means we won’t have to start from scratch, learning sales techniques or getting comfortable with the process. Building active selling into our business routine will prepare us for the hard times and set us up for success more than we give it credit for.

It’s something I’m realizing after the fact. 

I got comfortable. I lost a few accounts around the holidays (which everyone knows is the worst time to sign new ones). And then had to start an email campaign from scratch – including taking a full day just write my first email of the sequence and sort out the software.

Don’t be like me. Don’t get comfortable once you’ve ‘made it’.

Always Be Closing.


By Nikki Gillingham

You can follow my journey balancing work and travel on Instagram and my blog, or check out my business for marketing tips!

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