Freelancer Life: How to Work Smart and Stay Calm (in Your Pajamas)

April 12, 2017 • 7 min read
Sara Finkelstein

Sara Finkelstein

Writer, Editor, Content Creator


It can be exhilarating to wake up on your first day of self employment and not rush to the office by 9:00AM. There’s no morning scramble, no waiting for the shower to heat up, and no battling rush hour traffic as a freelancer.


It can be disconcerting too. What should I tackle first? How do I make myself work instead of going back to sleep? Is it procrastination if I’m completing my housework?

Plus you have to do it all by yourself. There’s no IT department, no human resources, no office supply closet, and no one delegating projects. How can you ensure that your paycheck keeps coming?

Working smart when nobody tells you what to do is hard. Keeping panic at bay when you’re overwhelmed or when the pipeline runs dry is hard.

Managing the Day to Day As a Freelancer

I am an example of what not to do when it comes to managing finances and marketing as a freelancer.

However, when it comes to the day to day reality, I have finally amassed some foolproof wisdom. This advice is based on experience, and from making mistakes. I asked some of my friends and advisors for their two cents too.

This is our best advice.

Consider a schedule

Not everyone thrives as a result of structure. In fact, one of the advantages of freelance life is you aren’t bound by a schedule.

But some people get overwhelmed by too many choices. It’s scientifically proven that many choices often leads to dissatisfaction. Barry Schwartz, a professor at my alma mater wrote about this phenomenon in The Tyranny of Choice. He explains that while we relish our freedom, too much of it can feel daunting.

For some people, creating a routine can be helpful. You don’t have to stick to it exactly, but it’s nice to have an outline of your day before you begin in case you need direction. You won’t have to decide each and every morning how to approach your work and when to begin.

You might be surprised at how calming it can be to set a routine, even if you are somebody who chafes against structure or a regular schedule.

Take advantage of your flexibility

As freelancers, your time is our own. But that can lead you to feel compelled to work 24/7. I recommend that you don’t.


You’ll have deadlines piling up sometimes. Be sure to balance that by taking advantage of your flexibility. Celebrate the fact that you can follow your own flow if you feel inspired at 3 AM. If you finish your work at 2pm, no need to sit at your desk until 5pm. Did the sun finally emerge in Seattle? Lace up your running shoes and hit the outdoors!

My friend Lisa Halpern, creative director at Third Eye Productions, has been a freelancer for more than fifteen years. She loves that she can stay in her pajamas all day, take a break when she needs one, and work on her garden in the afternoon. I even have a freelancer friend who has answered work calls on ski lifts while taking advantage of weekday pricing.

Find collaborators

Leaving the 9 to 5 world can feel like you suddenly have to figure everything out on your own. You don’t really have to do it all, explains Michael Stearns, owner of Hybrid3. “You can always find people or apps to do things you don’t feel confident about or really dislike doing.”

An added benefit of collaboration is that it can go back and forth. Sometimes Michael needs writers to help with proposals, and sometimes his writers need design for their websites.

Expect ups and downs

Freelance life is neither steady nor predictable. It helps to know that that’s normal. You’re not doing anything wrong. It’s just the nature of the work, not to mention business cycles, fiscal years, budget cuts, and other factors outside of your influence. Not having control is stressful. But if you expect ups and downs, you won’t be as rocked.

You can even plan for them, Career Coach Erin Ewart, of Erin Ewart Consulting, advises, and use slow times to update your website or refine your business plan.

Is there a flipside to this volatility? As a freelancer, you get to work on a remarkable variety of projects with a range of clients. Sometimes you even have a month off in the summer! It’s an ideal set-up for people who are generalists, perpetually curious, or get bored easily.

Seek connection


If you are an introvert or just love being at home, freelancing might be for you. However, many people crave human contact, and it can feel lonely or isolating to work solo from home. Here are a few ideas:

1. Work from a coffee shop with Wi-Fi. You might find a slew of regulars who do the same thing.
2. Join a co-working space, an innovative shared-economy model, where workers reserve desks or offices in a common workspace, with almost unlimited flexibility.
3. Create informal freelancer groups using Meetup, Facebook, Townsquared, or other online tools and communities.
4. Engage in frequent Skype, Google Hangouts, or other video calls with clients and colleagues, so you feel connected to them.
5. Organize regular coffee chats with friends and colleagues.

Stay calm

The confidence that the next project will in fact arrive is born out of experience. As Lisa Halpern relates, “I’ve been doing this for so long, I understand there are peaks and valleys. The challenge is to stay calm. It’s like the stock market. Just because it drops, doesn’t mean you’re lost. It’s a question of weathering the storm.”

Think of a psychological magic carpet that provides the sensation of stability, even when you’re not on steady ground.

Learn from mistakes and move on

“Do not look backwards except to learn,” counsels Michael Stearns of Hybrid3. You will make mistakes. We all do. If I hadn’t made mine, I wouldn’t be able to write this column. But it doesn’t help to dwell on regrets. “Life cannot be lived backwards,” Michael reminds us, “except to gain perspective on life moving forward.”

Take care of yourself

It’s liberating to be your own boss. You get to make your own schedule, fly by the seat of your pants, and pick your projects. But it can also be exhausting and overwhelming.

Be sure to take time for yourself. Take breaks, take vacations, go to the gym. Freelance graphic designer Stephanie Hinderer agrees. “I always used to feel guilty about taking time off, but I would get really burned out really fast,” she says. “Then I learned that if I didn’t leave time to inspire myself and to rest, it was hard to find the inspiration for my design work, as well.”

Do you have additional advice from your own freelance experience that you’d like to share? I’d love to hear your thoughts!

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