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How to Break Free from the 9 to 5


The 9 to 5 is Broken. Yet, we continue the monotony, the rat race, the struggle. There is a better way to work, a way that benefits both the organization and ourselves. We just need to define what that is and then set a plan in motion to make it happen.

I recently spoke with Krista Gray, a freelance writer and owner of GoldSquare, on how she broke free from the 9 to 5.

The result? Better work, more freedom, more joy.

Read the interview and get inspired on making work, work for you.



Tell us about your background. In what industry did you launch your career, and what was that like?

I started my career in eCommerce, working for several individually-owned retail businesses before jumping into consumer tech (startups).

My time in-house with small ecommerce companies and startups provided a solid foundation for the work I do now. I loved working with cross-functional teams and learned a ton. The hardest part about being an in-house employee was adhering to pre-established guidelines for producing good work; and I never had an appetite for office politics or culture clashes.

What are you doing now?

In addition to my work as a freelance writer, I own GoldSquare, a company I created to help individuals, small businesses and early stage startups shine online!

Owning GoldSquare means I get to focus on the different parts of former jobs that I loved: building relationships with clients, making their visions come to life and helping them streamline their digital content and marketing needs. Nothing makes me feel better than serving as a catalyst for someone to share their work and passions with the world.

What made you decide you wanted to “break free” from the 9 to 5?

I was exhausted spending 24/7 thinking about someone else’s dream. There was little variety, and the face time culture wasn’t a good match for the way I work as a creative. For me, inspiration and motivation ebb and flow – and often times, I just couldn’t produce my best work during ‘business hours’, which was frustrating.

Now, I work when the fire strikes, which is often later at night or very early in the morning before emails start pouring in.

What steps did you take to make the transition?

I started freelancing while working full time, and did that for a couple of years. I worked on small consulting projects for friends of friends with startups and booked interesting writing/content projects that came my way. The assignments helped me make extra cash (which I banked 100 percent) for my eventual leap while helping me build confidence, a reputation and client portfolio.

What fears and roadblocks did you have to overcome as you were making this transition

Leaving a full-time salaried position is scary – there’s no other way to say it. Coming to grips with the fact that I would have to make sacrifices in my lifestyle was a little bit difficult, but has been so worth it.

I was also afraid to fail and had to get over that mental hurdle too. For some crazy reason, I was worried about folks judging me or thinking I wasn’t good enough to do my own thing or serve top-notch clients in the space.

Of course, that has been the opposite of true. My friends, family, and former colleagues/managers have been the best sources of referrals and motivation during tougher times!

Being aware of the mental hurdles that come your way during any change is key. How is it going now as a freelancer? What’s working for you?

I’m about six months in now, and it’s going well. Lining projects up in advance (pre-booking months ahead) has helped ease my financial anxiety while keeping me busy. I’ve also established a daily routine and stick to it, which makes gives my time a sense of structure.

There’s always challenges with change. Now that you’ve made the transition, what’s your biggest challenge, and how are you tackling it? 

The biggest challenge has always been feeling lonely. Making it a point to connect with other freelancers and get out of the house helps mix up the day while giving me the social time I miss from working in an office. I’m part of a few online networks and communities like Dreamers // Doers, CloudPeeps and Freelance to Freedom Project that also give me that same feeling of ‘water cooler talk’ – and I started teaching The Bar Method for a further part-time social fix IRL.

Many 9 to 5’ers are afraid to make the leap because of the uncertainty that comes with this transition. How do you deal with financial stress or the uncertainty that comes with freelancing at times?

I always plan ahead as much as I can. Before making the leap from full-time to freelance, I had saved up enough money to cover my most basic expenses for about two years. I realize that isn’t feasible for everyone, but having a small nest egg certainly makes things easier mentally.

I also try to plan project work as far into the future as I can, so I aim to book my work queue to capacity six to eight weeks in advance. That helps a ton, but doesn’t save me from stress entirely — timelines change, clients cancel projects, companies lose budget money, etc.

To ease the anxiety in those circumstances, I keep a few small recurring gigs that bring in minimal money each month, and I constantly iterate on experiments for growing my business. I take advantage of downtime to learn new skills that bolster my client offerings, as well as work fun/odd jobs when I get the chance. I helped out at a jewelry boutique during the holiday season two days a week when I first launched GoldSquare, and I never turn down a business-related focus group invitation. They pay well and they’re fun!

I know other freelancers and new business owners who drive Lyft or Uber, nanny, or tutor on the side. Not only do these types of small supplemental jobs provide extra income, but they also require a brain switch that forces decompression. This has personally always left me feeling refreshed when I come back to client work which is a real added bonus.

It might not work for everyone, but it’s worked well for me so far!

What type of person would you encourage to “break free” and pursue a freelance career?

I think anyone with a creative or entrepreneurial spirit can be a good fit for the freelance life. However, it’s key that folks considering the leap can hold themselves accountable, are comfortable with rolling up their sleeves, and really want to make it happen.

You are 100 percent responsible for driving activity. There’s no room for procrastination when you need work to pay your bills, and no one is going to chime in on that email chain for you.

I’m more dedicated than I’ve ever been, but it’s on my own terms.

Thank you, Krista for sharing your story with us! You can learn more about Krista’s work here

Belma McCaffrey

Author Belma McCaffrey

More posts by Belma McCaffrey

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