One of the greatest things about being a full time calligrapher is the freedom to work from home and another is of course being your own boss. The flexible schedule, the ability to manage your projects and clients the way you want to, and the freedom to focus on what you really need to do without coworkers interrupting you are just some of the perks of my job.

However, working from home can bring both isolation and misunderstanding from others. Our graphic designer, who also works from home, says some members in her family still ask “so, you don’t work, right?” It is always a sucker punch to the gut when people STILL can’t understand what you do or take you seriously because you don’t work in a typical 9-5 office setting.

I’ve experienced a wide range of creative entrepreneur workspace scenarios, and they all have pros and cons. I have worked from my parents’ home, in a small studio in Hermosa Beach with one assistant, in a home office in my own house when I moved to Virginia, and currently I work in our own studio outside the home. Alyssa has worked out her own balanced work-from-home life, and together we’ll cover some of the positives and pitfalls of working from home and being a creative entrepreneur in general.

By knowing what you are getting yourself into, we hope this post can help you figure your ideal working environment or, at least, offer you an opportunity to say “me too” from one fellow creative to another 🙂

On the working-from-home dress code:

Pro: Working from home gives you the absolute freedom to work from your yoga pants, without makeup, and make your own hours. Personally, even when I worked at home I still showered and got dressed every day because it helped get me going – but HAVING the option is still a perk that I occasionally take advantage of even when I head to the studio. Alyssa takes full advantage & sometimes “gets ready for the day” at 5pm, lol.

Con: It’s hard to not want to go take a nap or switch on the tv midday when you’re running out of steam and in your comfy clothes. You can feel pretty blah being in your workout clothes all day, especially if you didn’t actually get in a workout!

On working from “anywhere”:

Pro: Making your own hours gives you the freedom to work from anywhere at whatever time suits your schedule. Alyssa just needs a phone and laptop to work, so she really can taker her work anywhere! Technically I can’t do my calligraphy anywhere, but I can take it on travel weekends with my husband. Also if I have appointments in the morning, I can just work later in the day – the shifting schedule is definitely a perk.

Con: Freedom to work from anywhere at anytime can make you feel like you should always be working. Especially as a small business owner, it feels like I should always be getting ahead on the schedule, thinking about future goals, sharing on social media, replying to emails, etc. You have to consciously decide to stop – we’ve gotten much better about not working evenings & weekends, but it took actually cutting back on the number of orders we accept and consciously “turning off” each evening and weekend.

On limited social interaction:

Pro: Working from home means it’s quiet without interruptions – this one was key for me personally as I need to really focus when I’m doing my handwritten work. I am also an introvert so this is really when I get recharged.

Con: It can be lonely and sometimes you have no human interaction for the entire day. Alyssa, who is slightly more extroverted than me, experiences this one big time and has had to schedule lunch dates and happy hours with friends to make up for the lack of social interaction. 

On home life distractions:

Pro: Having the opportunity and time to do housework & errands during the week to avoid the crowds is a HUGE perk. The amount of time I save when I go grocery shopping at a non rush hour time is a thing of beauty. Also, I can pick when I want to drive anywhere to avoid traffic as well.

Con: Your significant other or roommate may come to expect that you can handle all the housework/cooking since you’re “home during the day” but oftentimes work is so busy you don’t have time to do any housework at all, and that stack of dirty dishes or laundry isn’t getting any smaller….this is without adding kids to the combination, which I imagine gets significantly more difficult! It is definitely a good idea to communicate with your loved ones about your “office hours” and draw some good boundaries and expectations with them. These conversations will also help with the guilt you might feel about leaving those dishes untouched or laundry un-laundered.

On being your own boss:

Pro: This means you have no one to report to but yourself {as long as your work gets done of course}. Even a client-contractor relationshiop is different than a boss-employee relationship. When I am working on a project for a client, I am getting paid for my services, not when I clock in and out.

Con: People don’t often consider that you have a “real job” or real work hours, since you work from home. Oftentimes friends will expect you to take prolonged lunches or off from work completely because you have no one to report to, except yourself. And you’re the one that has hours of catch up to do the next 2 days for the work you missed. Also, vacation days are kind of nonexistent, especially at the beginning of your business since the days you don’t work, you don’t get paid! Just like you need to communicate to the people you live with about expectations, it is important to educate your friends on what your day actually looks like so they know you aren’t being rude because you can’t just go get your nails done with them!

A note about explaining your job to others:

The not having a “real job” comment can be a biggy. It can be so difficult to explain your job to others, and in general people may think you don’t work as hard or that you have a ton of free time. When you own your own business or work from home even if you don’t own the business, there is a mentality that you need to always be working, always thinking of the next goals or projects, always available, the list goes on and on. Just remember that if you like what you are doing and are working hard doing it, it doesn’t matter what people think. This is a great skill to start honing, especially as you launch your career as a calligrapher. Trust me, people think I just write pretty for a living, and I had to learn early on that it’s OK if they don’t fully understand what I do. The best thing I can do is be proud of what we’ve built and continue to educate people on my business, appreciate the balance in life that I do have and be grateful I get to do what I truly love every day!

The truth is there are definitely significant perks for ditching the 9-5 corporate life, but there are also drawbacks, both logistically and mentally. There are pros and cons for both, and only you can decide what is best for you and your family.

What are YOU most grateful for as a small business owner or what are you most looking forward to when you eventually take the leap? Tell us in the comments!