This post originally aired as an episode of my podcast, The Fearless Creative.
Make sure you subscribe so you never miss an episode! If you’d rather read instead of listen, I’ve included the abridged transcript below.
Welcome, welcome, welcome to the show everybody. I am so happy to be here talking to you. I’m recording this episode on Sunday…and I had a very productive week last week and a nice relaxing weekend. We went up to the Gem and Mineral show yesterday, which was a lot of fun. There’s one in Woodland Park and another in Lake George…The area where we live in Colorado is a hotbed for gems and minerals. We actually mine some of the world’s best Amazonite, and so it was really cool to get up there and meet some of these miners and crystal enthusiasts in person.
I’ve been putting the final touches on my book before it goes to my editor, and this week, because I was so busy, I gave myself a bit of a mental break.
Now those of you who know me well know I love my bullet journal. It’s how I set goals, it’s what keeps me on track, but sometimes when I’m really busy I start to get the feeling that I’m living in my to-do list…almost like my to-do list is running my life rather than me using the to-do list. And so this week I made the conscious decision not to use my bullet journal at all.
I haven’t made a to-do list at all this week. I just had my goals for the week that lived in my head and in my writing calendar, and anything else that I really needed to remember to do, I put on a sticky note. There were only two or three things that I needed to write down so I wouldn’t forget, and it was so liberating not to have to consult this list all day. I feel like it really helped me stay in the present moment and be more productive.
So if you’re ever feeling overwhelmed, I would highly recommend stepping out of your to-do list just to see how it feels. It’s counterintuitive, but it works.
This week I also got some exciting news…I heard from a friend of mine who’s also my neighbor, and he told me that he is officially giving notice at his job to start his own consulting business. He’s been talking about this for a while, and he’s been taking some steps to get things rolling…and I was really excited when I heard this because I love it anytime someone decides to stick it to the man and strike out on their own.
But it also got me thinking about some of the hurdles that I faced when I first left my 9-to-5 to write full time and some of the challenges that every self-employed person has to deal with — especially creative types running creative businesses.
That’s why this week I’m talking about the four big hurdles that every creative entrepreneur will face when going full time with their small business and some of the ways that I’ve overcome them.
But first, it’s time for this week’s Discovery segment. This is the part of the show where I talk about something useful or interesting that I’ve found helpful this week. And today that is a book called “A New Earth: Awakening to Your Life’s Purpose” by Eckhart Tolle.
In a previous Discovery segment, I mentioned the podcast series hosted by Oprah where she has conversations with Eckhart about the book. I may have enjoyed those conversations more, but I actually listened before I read the book, so it’s tough to compare.
But this is the book I’ve been reading in the mornings, and to be completely honest with you, it’s taken me a little while to get through. Eckhart Tolle can be challenging to read because he’s a little woo-woo and out there. But I’m glad I didn’t stop reading because it’s a book that really challenged me and gave me some big a-ha moments about my life. It’s one reason I ditched my to-do list this week, and it’s really been opening me up to the idea of surrender and not having an adversarial relationship to the present moment.
Once again, the book is called “A New Earth” by Eckhart Tolle. It’s definitely worth your time to read so that you can open your eyes to ways in which you may be sabotaging your own happiness without really being aware of it.
But let’s go ahead and dive into today’s topic: the four hurdles you’ll face when you go full time with your creative venture.
The first hurdle, of course, is…
I want to talk about the income piece first because this is kind of the hardest part about being self-employed. If you’re working your way out of your day job gradually, which I highly encourage, it can seem like it takes forever to get to a point where you feel comfortable leaving your day job. If you’re jumping in with both feet because you quit your job or got laid off, this can be a really stressful ramp-up period.
The good news is that if you work for yourself, you have the potential to make way more money than you ever made working for someone else. You aren’t paying the price for keeping the lights on at someone else’s company, but you are paying to keep the lights on at your own business (and in your own house!), so whatever you think you need to earn to replace your day job income, add 20 to 30 percent.
When you are self-employed, you are going to be responsible for paying state and federal tax, medicare, and social security. You also might be responsible for paying sales tax, and you’ll definitely be responsible for paying for your own health care.
So if you have a regular job, your employer withholds taxes from your paycheck for you. That’s over now. So I pay my federal taxes monthly after I get my salary, and I pay state taxes quarterly. Then I settle up with the government at the end of the year, and if my accountant has done a good job, I don’t owe anything more. I might get some money back, though that has yet to happen to me.
One distinction that people often don’t understand is that if you have a regular job, your employer also pays half of your social security and medicare taxes. When you’re self-employed, you’re considered the employer and the employee, so you have to pay both.
But the biggest expense that self-employed people have to account for is health care.
As a self-employed person, you will be responsible for selecting and paying for your own health insurance if you live in the United States. Now, if you’re really lucky, it’s possible you can pay to get on your spouse’s health care that he or she gets through work. If that’s an option for you, I’d definitely explore that. You’ll probably be able to access higher-quality care for less than you’d pay to get your own plan.
If not, you get to tackle the health-care marketplace, where you can expect to overpay for mediocre health coverage. So since Ben and I are both self-employed, I handle our insurance myself through the marketplace. We pay about $700 a month for the two of us this year. I’m 28; he’s 39. (Of course, your age will factor into what you have to pay.)
I sprung for a middle-of-the-road plan for us because I sometimes need to have bloodwork done to monitor my platelets. Ben does very physical work, and so I wanted him to be taken care of if he ever got hurt on the job. In hindsight, I think a middle-of-the-road plan may have been a mistake. He’s been to the doctor once this whole year; I haven’t been at all. So we probably could have gotten away with a cheaper plan and saved maybe $100 a month.
If you are young, in good health, have no major health conditions that need monitoring, my suggestion would be to go get yourself the cheapest catastrophic health plan available and then use Teladoc for regular doctor’s visits. It’s an app. I’ve never used it myself because I rarely get sick, but my dad really likes Teladoc, and he said it’s about $40 to get a doctor to check you out.
If you’re older or you are in and out of a doctor’s office quite a lot, don’t cheap out on your health plan. Really take the time to look at the benefits and spring for something nice. I like it when there’s a set out-of-pocket cost for a visit to your provider.
Neither of us has dental or vision coverage; we just pay on an à la carte basis for our teeth cleanings and eye care. I find this works out to be cheaper. I wear contacts, but I have really good teeth and hate the dentist, so I go in for a cleaning about once a year.
There are three suggestions I’d make around the topic of income if you’re getting ready to leave your day job.
- Have a nest egg. Save up at least three months of living expenses for yourself before you quit. You might want to save up more if you have kids, but it’s also going to depend on whether you’re partnered or single, how much debt you have, and how steady your creative venture is.
- Get out of debt, and stay out! Jumping into self-employment is much less stressful if you aren’t saddled with a bunch of debt. When I talk about debt, I’m not referring to a mortgage. Most people will still have a mortgage or pay rent, and owning your house is always a better investment than renting. Even though you’re paying interest on your loan, your house should be appreciating or gaining value that outpaces what you’re spending on interest. And you’re gaining equity in that house with every payment. I’m talking about credit card debt, car payments, student loan debt…Stuff like that.
- Look at scalable income. Can you grow your income or turn on more streams of income if you want or need to earn more money? If you’re freelancing, for instance, you can always look for new clients to get more work. Before you go into your creative venture full time, really consider how you could generate more income if your personal or business situation changed.
So that’s my best advice around income. Now let’s look at your schedule.
One of the best parts — if not the best part — of quitting your 9-to-5 to go work for yourself full time is owning your time. You are no longer selling your time off hour by hour as you creep toward death. (Just kidding — but really.) You own your time, which means you can use it as you choose.
This is definitely my favorite part of being my own boss, but it was also one of the hardest things to figure out when I went full time. Now, full disclosure: I came from a Millennial-run startup with flexible hours and unlimited vacation. No one was standing over my shoulder all day…No one would scold me if I came into work five minutes late. If you’re coming from a highly structured corporate environment or government job where you were intensely micromanaged, this is going to be much harder. I’m not saying this to discourage you; I just want you to prepare for it so you aren’t blindsided.
When you become your own boss, suddenly you no longer have another person who’s responsible for structuring your time — even indirectly. Because if you worked on a project-by-project basis or had deadlines or quotas, you still had someone managing your time. They were just measuring your productivity instead of hours spent at your desk.
The closest analogy I have for this is going from high school to college. When you go to college, suddenly you don’t have a parent or guardian around. You can stay out late. You can eat crappy food. You can drink yourself into a coma. You don’t ever have to go to class if you don’t want to. But you will fail out and waste tens of thousands of dollars…and, of course, you’ll waste your education.
When I went off to college, I found that I had way more free time than I ever had in high school. It took me a minute to get my footing, but I eventually figured out that I should be filling some of that free time with an internship or a job.
The same applies to quitting your 9-to-5 to work for yourself. When you’re self-employed, no one knows or cares if you blow off work. No one is going to micromanage you, so you need to be naturally disciplined.
If you’re not naturally disciplined, you need to set hard rules for yourself — especially if you work from home. Those rules could be things like “No social media during business hours” or “No Netflix over lunch,” or “no cleaning when I should be writing.”
This isn’t a hard rule I have, but I like to get dressed to go out every day even if I plan to work from home the whole time. For one thing, it minimizes awkward pajama interactions with the UPS guy at 2 in the afternoon, but it also puts me in a work mindset.
If you work from home, you should prepare for some potential conflicts around your schedule…
One point of conflict Ben and I had when we first started living together was that Ben doesn’t care about weekends. Personally, I like to keep banker’s hours, but to Ben it doesn’t matter if it’s Monday or Saturday…He works when he needs to work and takes off when he wants a break. The days of the week may no difference to him.
The first year we moved to Colorado, he wanted me to take off during the week during snowboard season so we could go to Breckenridge or A-Basin when it was less crowded. He didn’t think it was a big deal if I could just work over the weekend, but it really threw me off not to have a regular five-day week. Eventually, I had to set some boundaries with him that I wasn’t going to take off on a weekday unless it made sense with my production schedule.
You might not have that problem if your spouse works regular hours, but you might have a different problem. Your spouse might not understand why you can’t take care of the kids while you’re working if you work out of the home. Or people might expect you to do extra things for them because you don’t have to stay in the office all day.
It’s really awkward and hard to set boundaries at first, but you eventually get better at it because you have to.
If this continues to be a problem for you, it might be a good idea to work outside the home at a coffee shop for a few hours a day or pay to work at a co-working space so you have an actual office to go to.
I think it’s important to note that I don’t ever write for a full eight hours. I just can’t. If I wrote for eight hours straight, by the end of the day I would be no more than a shriveled husk of a human being.
If I’m writing fiction and I’m generating all new material, I might write for 4 to 5 hours. That’s pretty decent. If I’m doing a developmental edit, this is about the same. It’s only when I get into the later stages of proofreading that I can work on the material for seven, eight, nine hours. But I like to work regular hours anyway, so if banks are closed, I’m probably not working.
This really helps me with my next hurdle, which is…
Managing Your Creative Energy
Now when I talk about managing creative energy, I mean being able to produce and produce and produce day after day. Because this is the life of a creative person. In most cases, you get paid based on output. And this can be challenging if you’re not super prolific or you aren’t used to producing constantly. I was used to this type of production, but I still had to find workarounds and hacks to better manage my own creative energy.
So this is my podcast, and I would be remiss if I didn’t tell you that my upcoming book Creative Morning Magic is going to give you the most critical tool you need to manage your creative energy. Shoot me an email at firstname.lastname@example.org if you would like a free review copy before the book is released.
But besides an enriching morning routine, one of the most important things you can do for yourself to manage your creative energy is to do your most important work first. I was not born a morning person, but I still do my very best work in the mornings. I always have a big writing session before I even eat breakfast.
And when you’re doing your first stint of heavy creative work, it’s really important to try to insulate yourself from the rest of the world as much as possible. Don’t watch the news. Don’t go on social media. Don’t check your email or your sales stats. All of that really derails your creativity and lowers the overall quality of your work.
I organize all of my writing and creation sessions around my meals. So as I said, I do my first writing session before breakfast, which lasts about an hour and a half…maybe two hours if I’m on a roll. Then I eat a late breakfast, and I’ll have my second writing session of the day. This can last about three hours before I’m completely depleted and I have to go eat lunch.
I eat breakfast and lunch super late. It’s not necessarily the most healthy, but it helps me get more work done. After lunch, I’m kind of winding down, and I usually won’t have any more writing left in me. This is when I might create ads or look at finances or something undesirable.
I call this “low-value work,” and so I save it for that point in the day when I’m feeling like a wet sponge that’s been fully wrung out. Sometimes Ben comes home around this time and wants me to look at stock charts, but I just don’t want to spend any more time squinting at a computer screen.
Being on a computer for so long is one thing that’s really hard on me physically. I do have an adjustable-height desk, an ergo keyboard, and a laptop riser…I did a really in-depth blog post on my ergonomic desk setup and some of the tools I use to not be a hunchback, but if you’re spending your entire day behind a computer, it’s really not good for you.
I take a walk almost every day with my dogs. I do yoga several times a week. I’m also really motivated right now to get back into martial arts, because I never had any carpal tunnel symptoms back when I was boxing and hitting people all the time. I got out and went for a run and hit the bag on Friday, and it felt so good just to get really physically aggressive and sweat.
Staying active is just super important for your physical health if you’re a laptop entrepreneur, but it’s also great for your creative energy. Nothing recharges me better than going for a hike or hitting the bag. It’s just like a reset for the brain.
Mental rest in general is important for managing your creative energy. I like to take time to do nothing. I like to get out in nature and get away from the computer and away from my smartphone. This is one reason why I try not to work on the weekends. Weekends are the time when I recharge my creative batteries.
And finally…sleep. I cannot tell you how critical sleep is to your overall creative performance and productivity. If you currently get five or six hours of sleep and you think you’re doing just fine, it’s only because you literally don’t remember what it felt like to be fully rested! You’re probably also compensating with heavy caffeine.
I’m telling you: If you can find a way to get eight hours of sleep a night, your performance is going to improve so dramatically you won’t even believe it.
Lately, I’ve also gotten really into sleep hygiene, which is basically optimizing your sleep conditions so that you can make the most of the rest that you get. Avoiding blue light before bed is the first pillar of sleep hygiene, but equally important is eliminating any artificial light coming into your bedroom and getting your sleep environment as cool as possible.
The light we get before and during sleep controls this super-complex symphony of hormones that our bodies release. Light can either help us fall into our natural circadian rhythm or prevent us from getting into that good natural rhythm. The other night Ben was like, “Why do you hate the air purifier?” because I’d covered the bright red and blue lights with duct tape and put something over the top of it. Those lights on the machine are tiny, but they were filling our entire bedroom with weird artificial light. We also have some orange light from the street that comes in through the blinds, so I sleep with a sleep mask, too.
Taking care of artificial light really makes a difference — especially if you’re not getting quite enough sleep or you struggle to fall asleep and stay asleep.
Most mornings I wake up naturally…I said my favorite part of being an entrepreneur was owning my time, but this week I think I actually came to the realization that my favorite part is not waking up to an alarm. About half the time I wake up naturally just because I reach a good place in my sleep cycle and my body wakes me up, but when I don’t, Ben wakes me up with a kiss before the markets open at 7:30, and this to me is just the best part of being self-employed.
So sleep is super important for everyone but especially important for creative people.
Now that I’ve covered managing your creative energy, that brings me to the last hurdle of quitting the 9-to-5 and going full-time with your creative venture, and that is…
Now when my dogs were young, socialization was our number-one focus. Anytime you get a new dog, you want to take them to the dog park, the pet store — really anywhere you can — so that they can get used to people and other dogs and learn to be friendly out in public.
Yesterday when we took Nelson to the gem show, he was super weird and afraid of everything, which tells me we have a lot of re-socializing to do with him.
Humans are just like dogs. We are social creatures, but if we spend too much time by ourselves, we start to have a harder time socializing.
This is especially true if you’re an introvert, which Ben and I both are. Now I’m actually really good at socializing with one or two people at a time — especially if I know them — but I find crowds and big groups of new people exhausting. In truth, I’ve always found them exhausting, but when I worked a full-time job I had to do it out of necessity. I was generally more annoyed with people back then because of the constant forced socialization, but I was more practiced. So I could network if I had to.
If you quit your job to become self-employed, you will no longer have a built-in group of work friends. You will no longer have structured happy hours that someone else plans. You will have to engineer your own social opportunities.
I’ll be honest: This is one area of self-employed life that I have yet to master — partially because I really enjoy my alone time, and partially because Ben and I really enjoy each other’s company. He’s better at socializing with strangers, but he hates to make plans, so he’s often reluctant to follow through when we make social connections.
But there are two really helpful things I do to maintain a connectedness to the creative community: I have a monthly mastermind group of authors that I’m a part of, and I try to make it to at least one industry conference or retreat per year.
I find that writer-centric events are fabulous for making other introverted author friends because writers tend to spend a lot of time alone. When they’re put in a room with other writers, they’re actually really friendly. Conferences are great for turning Internet friendships into real-life friendships, so I would highly recommend going to one that is geared toward creatives like you.
So if I hadn’t made it clear throughout this episode, quitting the day job to go full time has been a wonderful decision — one of the best decisions I’ve made in my life. But it’s also posed some really big challenges that I continue to work through.
If you’re thinking of making the leap or you’ve already taken steps to quit your 9-to-5, I would just say not to expect too much from yourself right off the bat. If you get into it and it’s not quite what you expected, you’re not alone. Everybody struggles at some point in their self-employed journey.
I’ll see you next time, and happy creating!