(Art Credit: Sisi Recht)

If you’ve ever worked at a traditional job, whether it’s in the service industry, an office job, or something else, you know that having a great boss makes all the difference.

On the other hand, you could be working your dream job naming colors for Crayola crayons, but if your boss is a nightmare, you may fantasize about quitting. A good boss is everything.

You Get to be a Cool Boss

Whether you're just getting into the freelance game with big goals of working for yourself, or you’ve been successfully running your own business for years, I want to remind you that you always have the opportunity to be a cool boss. The wild thing about working for ourselves is that we dream about how ideal it will be while we work our 'regular jobs', and then when we finally become self-employed freelancers and quickly get caught up in the grind of making a livable wage. We forget how to treat ourselves as an employee.

Today I’m sharing some things that you can do, even in the beginning stages of your business, to keep yourself on the World’s Best Boss List:

1. Disconnect from Work

If your office boss demanded that you check your work email at every waking moment, respond to requests within minutes, work nights and weekends, it was probably an amazing day when you finally left to become a freelancer. Still, we often feel like our business depends on our immediate response to all inquiries, insane work speeds, and non-stop hustling. But this just isn't true. Working constantly with no breaks to recharge does not make you more productive or more money. In fact, it will burn you out quickly. Set healthy boundaries with your business right from the beginning.

Determine the hours that you are available to respond to work requests and when you are not. Make those boundaries clear.

I tend to work quickly and personally like to get things done immediately if I can. I don’t always follow my own advice, so I’ve been known to answer emails and do work at night, especially in this past few years when my boundaries were shattered due to the pandemic. Still, when I complete a project or respond to an email at 10 pm, I do not want to set the expectation that this is a normal response time. In these cases when I’m working late at night, I use Google's ‘send later’ function so my emails go out the next morning.

Turn off all your notifications on your phone so that you are deliberate about when you look at email and social media.

If you find yourself checking your work email the second you wake up at 7 am, check your phone settings for Digital Wellbeing (android) or Screen Time (ios) and set parameters around when and for how long you can open certain apps like Gmail and Instagram.

Inform clients of vacation time and stick to it. Use an out of office message while you’re gone.

I used to individually email clients when I was taking time off, now I usually just put it in my email signature a month in advance and then set up an out of office email. This simple hack has made actually taking time off way more seamless.

2. Take Time to Celebrate

Did you used to live for an office birthday party? I’m not saying it’s as good as a real party, but the chance to get away from your screen and get some free cake is undeniably appealing. I remember one Valentine’s Day early in my career when my company randomly invited everyone up to another floor of the office where a candy buffet was set up, complete with little bags for all the employees to load up. Those kinds of random breaks from the regular day-to-day are what makes work fun.

How can you inject this into your business?

When I celebrated my 8th anniversary of self-employment I sent myself chocolate-covered strawberries, which I wrote off as a business expense. I also held my own ‘office party’ for the holidays, which really meant I got some good takeout food and took the afternoon off.

Schedule in some fun

Even if you don’t have the extra budget to buy special work treats for yourself, what can you do for fun? Can you put some random days in your Google calendar for this year and mark them as Best Boss days, and then pledge to take them off when you get to them? How about writing out a few cards to yourself saying what an excellent job you’re doing or wishing yourself a Happy Birthday, and asking a friend or partner to drop them in the mail at scheduled intervals?

Or, you might use the aforementioned Gmail scheduling tool to write yourself emails from your personal account and schedule them for months in the future to be delivered to your business account. I know it sounds kind of silly but how fun will it be to get a message from your past self cheering current you on? Self high five! ✋

3. Give Yourself a Raise

Making good money is not the only way to judge whether a job is good, but it sure does help. If you’ve been in business for a while and haven’t raised your prices with clients, it’s time to do it.  In regular jobs, we usually expect to get at least a small raise each year. As our own bosses, we have to advocate for ourselves and our worth and ask for more money just as regularly.

With each new client, you should be edging your pricing up, and even with your repeat clients, you need to raise your rates after you’ve been working with them for a while. If you’re just starting out, the pricing and negotiating can feel overwhelming, and asking for a fair market price can be really intimidating. Remember that it’s a learning process. The advice I give is to start where you feel comfortable but be sure not to stay where you feel comfortable. I don’t want you making entry-level money when you’ve been freelancing for 3 years.

4. Make a Cool Workspace for Yourself

My partner used to work at Google in New York City, so I’m well aware of what an unlimited budget can do to make an office space cool. They had fully-stocked snack bars every 20 feet, a full-service free cafeteria, ping pong, video games, conference rooms that had New York City neighborhood themes, a library featuring a digital wall of books, and custom uber-cool wallpaper and art.

Your business may not have a Google budget, but you can still create a cool, inviting workspace for yourself that makes you happy to sit down to draw each day. Even if it’s just a corner of your dining room  - a nice lamp and a potted plant or a fun art print on the wall in front of you can do wonders. Honestly, something as small as a fresh desktop wallpaper can lighten the mood and make opening your computer feel refreshing. Do what you can to add some little touches to your work area to make you smile.

5. Don’t Forget to Socialize

A work happy hour or chat with coworkers in the break room can be the best part of your day, but working alone you don’t get that opportunity. Making connections with other designers is an integral part of entrepreneurial success and I recommend you set aside time in your week to connect with other artists and talk shop. Not only will you learn a lot about how others do business which may help you improve your own, but you’ll get a chance to bounce questions and vent client frustrations and take off that SOLO edge of being a soloprenuer.

So there we have it. Now is a perfect time to commit to being your best boss ever this year, whether you’ve been freelancing for ages or are still looking for your first paid gig. Which one will you implement for yourself today?