10 Things My Dad Taught Me About Being Your Own Boss

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When it comes to being self-employed, I can think of no greater inspiration than my own father. He’s been a freelance illustrator for nearly 30 years, doing everything from political cartoons to product designs to children’s books. He made a career for himself when there was no internet, really, and he had to go door-to-door with a giant portfolio in his arms in the summer heat, hoping someone would give him an assignment. Since then, he’s made a wonderful life for himself by doing what he loves, and through being diligent and professional, he’s never had to chose between his passion and his day job.

In celebration of Father’s Day, I thought I’d share with you the lessons he’s taught me — both in words and in example — about being your own boss. It happened that I followed in his entrepreneurial footsteps, but even if I hadn’t, his lessons are still hugely useful to anyone who wants to make the most of their career. Here, 10 things my dad taught me about working for yourself.

1. Set a routine and keep it. My dad has gotten up at 5:30 in the morning for as long as I can remember, and though it irritated me enormously when he would be chipper and productive on school mornings (when all I wanted to do was sleep), I now realize how huge that’s been for his success. It means that he’s able to get the bulk of his work done when he is most productive (aka early morning), and it keeps him in “work mode” by having the routines he associates with starting his day. I’m no morning person myself, but I’m online and making my coffee at the same time every day — 9:15 AM — and it makes working from home feel nearly as structured as being in an office.

2. Set your boundaries to separate the feelings of “work” and “life.” As kids, my sister and I never understood why my dad would get so angry when we’d call him from school and ask him to bring us something we forgot. We simply thought of dad as “being at home,” and therefore available when we needed him. But he would always remind us that just because he was at home did not mean he wasn’t working, and that we needed to respect his boundaries. We learned not to bother him during work hours unless it was an emergency, and to treat his office as off-limits — which made him ending the work day feel like he was coming home after being away.

3. When it comes to clients, always be a friendly presence. My dad’s most notable skill in life — aside from drawing, obviously — would have to be his ability to make friends and turn a conversation to the positive. He’s the kind of guy who will call up to complain about an issue at a store, and walk away with a friend and a huge gift card. He has mastered the ability to be nice, thoughtful, and light with people, especially with clients. He knows that to get what you want out of a situation, you need to make the person feel at ease (and never attacked, particularly when it’s out of their control). He always starts his professional calls with 10 minutes of chatting, and makes whoever he’s dealing with feel like a friend, instead of a stranger he’s trying to get something from.

4. Follow up. When he doesn’t hear back about something work-related, he follows up, because he knows that half the time, someone might have simply forgotten. He knows that it’s up to the freelancer to stay on top of things, and keep a clear calendar of what is happening when. A friendly reminder to a client can be the difference between getting a job and losing it, and he’s mastered the art of checking in (in a way that isn’t annoying).

5. Go the extra mile to make sure your client is a repeat client. A huge part of maintaining a client is doing a little above and beyond to make sure they are extra happy with the work. If this means going back for an extra round of edits, or tacking on a tiny bit of extra work, or giving a little freebie now and then, it’s worth to create a long and fruitful relationship. My dad is always willing to do a little extra, because it always proves to be worth it.

6. Know when to say “no.” On the flip side, when a client is being unreasonable or disrespectful, knowing when to walk away is essential. Just because you are freelance doesn’t mean you must take every job, regardless of what it does to your work/life balance or mental health. Standing up for yourself and advocating for your own respect as a professional is of huge importance, because if you don’t put your foot down, you will never get treated with the attitude that you deserve. And being comfortable with walking away from things is the key element in making sure you get that respect.

7. Create “colleagues,” even when you work by yourself. My dad has several work relationships — friends, clients, fellow artists — that span nearly three decades. These people are essentially “colleagues” to him, people he works with and learns from, who create a sort of human landscape to his work life. Finding and keeping these people close is huge when you work alone, because it makes the process feel less isolated, and creates the basis of a network (which all freelancers must have).

8. Create a clean, inspiring office space. My dad’s office was always a sacred place — a separate room in an isolated part of the house, which made his “work” time much more contained and mentally separated. While I don’t yet have room for a home office (soon!), I do take after him in the sense that my workspace at home is clean, organized, and always inviting to work in. (It has prime real estate in front of a big, east-facing window, which at least temporarily makes up for the fact that it’s not yet in its own room.)

9. Set your value, know it, and continue to increase it. One of the hardest things to do as a freelancer is setting a value for your work and truly being confident in it, but my dad has always shown me that the temporary discomfort in asking for money (and a good amount of it) is always worth the professional and financial comfort of setting your price points at an appropriate place. If you don’t advocate for your worth, no one will.

10. Work smarter, not harder. Growing up, my dad used to listen to the traffic report while drinking coffee and working, because it made him feel grateful to be able to work from home and do what he does. In his efficient, smart way of working, he taught me that if you understand when you do your best work, and are serious about the time you put in every day, your work days can be shorter and without time-wasters like a long commute. My dad embodies working smarter, not harder, and I hope to do the same in my career. (But I’m never waking up at 5:30 to do it. Lol.)

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