A little less than two years ago, I decided that I needed to start blogging about my pregnancy before our child went to college was born. About a year ago, I launched the grown-up version of the same blog, and (for some reason) people started giving me money to write and design things for them. Now I make about half my teaching income working less than a third of the hours I used to. My schedule is flexible enough for me to snuggle Monkey when he’s sick, or sit with a friend in labor until her husband gets back to town (true story!). I work with people doing cool things, and they appreciate (and pay me well for) my skills and experience.

I feel really grateful for all of this. I’m thankful that Science Guy works full-time to provide stability and benefits as a counterpoint to my freedom and flexibility. I’m thankful for the zookeepers teachers who take care of Fire Monkey and a dozen other tiny humans every morning for three hours. And I’m reaaaallllyyy thankful that my offspring takes long naps!

I also feel mildly…guilty? rueful?…let’s go with conflicted…that I’m no longer teaching. Not just because I’m on track to make at least as much income working a lot fewer hours, but because, for a good portion of my life, I believed that teaching was my Calling. And in the church environment of my upbringing, you don’t disobey your Calling.

But I realized over the years that Calling is as nebulous a concept as Passion. For most of mid-twenties, I did a lot of mental acrobatics trying to shoehorn the pursuit of my passions (which really were more accurately described as “temporary interests”) into a nobler framework of a divine Calling. (“God has called me to be a teacher! No, a wedding planner! I mean, a photographer! No, a teacher again!“) As it turns out, at least for me, Passion and Calling were just part of my need to have someone else tell me what to do with my life. As I sloooooooowlyyyyy matured emotionally and spiritually, I learned to listen to my own thoughts, emotions, and intuition, make my own choices, take responsibility for my own actions, and chart my own path.

My path usually looks like the graph on the right. But learning how to muddle through deftly navigate the ups and downs has arguably been more valuable than any actual forward progress I’ve made. I honestly never expected that freelancing would yield all of my personal income AND make a significant contribution to our family budget. (Because someone can definitely do the first without achieving the second, yikes!) For all outward appearances of my freewheeling freelancing life (GOING TO A DIFFERENT GROCERY STORE THIS AFTERNOON #WANDERLUST), I am actually a moderate to severe security whore. I don’t like ups and downs, or surprises, or not having three backup plans and running seven different disaster scenarios before trying anything. (Seriously, I don’t even like watching movies I haven’t seen before. This is why my cinematic preferences skew toward Land Before Time and The Brave Little Toaster.)

But as I was reflecting on my own entrepreneurial journey this week, I realized that my strong desire for security is not a handicap. Planning ahead and test-driving ideas before taking the plunge helped minimize the risk to our family and allowed me to grow at a sustainable pace. (Because obviously I have never bitten off more than I could chew. Ever in my life.) Could I have reaped greater rewards by taking bigger risks, probably. There are personalities and situations better suited to winner-take-all strategies than mine happen to be. And I’m okay with that.

So if you’re severely risk-averse like me but want to strike out on your own, here are some of the things I’ve learned from treading my own tangled professional path. Like just about everything in life, the key for me was finding an acceptable balance between being brave enough to take risks and being wise enough to know when and how to take those risks. I call this balance being Fearless. It’s not that I was never afraid of failure and rejection and risk (MBAHAHA)…I just tried to make decisions that led to less fear overall.

The Cautious Freelancer’s Guide to Starting a Fearless Business

Know your goals and values.

One of the most useful exercises my business coach had me do was create a Death List. What would cause me to close up shop and stop doing my thing? For where our family is in life, no amount of money is worth me having to work 60 hours a week and show up at set times in a set place. If I constantly had to do things I wasn’t good at and/or didn’t enjoy, my soul would shrivel up and start projecting so much negative energy that all small electronics in a mile radius would spontaneously combust.

Thinking about the death of your business may not jive with the whole, “If you can dream it, you can do it!” mindset, but knowing what would kill my enterprise means I know what to do to keep it alive. And from knowing my values, I can set goals from which all decisions can more confidently flow. I’m now better than I’ve ever been at setting and respecting boundaries around my time. It took me awhile to work up to this point, but I can now be choosy about which clients I work with and the terms of how I do that work. I went from charging $35/post to $120/post in less than six months, but I let that $120/post client go because I didn’t like writing about water filters. And letting them go made space for better clients to come along later.

Don’t dive all into your work-from-home dream or innovative idea until it’s on a sustained, upward trajectory.

Thanks to the explosion of law of attraction snake oil on social media, I’ve seen quite a few people betting all their chips on hope and desire, believing that if they want something enough, it will happen. I do believe there is some truth to making room in your life for what you want (see above), but it’s not enough to just create a vacuum without having something in hand to fill that space with.

I didn’t consciously decide, “I’m going to be a freelance writer, designer, and marketer!” until several people had hired me to do work, paid me well for it, and appreciated the results I delivered. In other words, I didn’t choose the freelance life…the freelance life chose me. (In the interest of full disclosure, I didn’t quit my day job to freelance. I wasn’t working full-time while my business was gestating. But I was raising a tiny, needy human being twenty-four hours a day, so I know a little bit about trying to fit a side hustle into an already packed schedule.) I made sure I could provide viable products and valuable services before investing time and resources into creating the infrastructure for my business.

Make a business plan that focuses on your process.

In my previous post, I wrote a lot about the importance of sharing your process with customers. Figuring out your process for yourself, and running through it a few times with some patient friends or clients, helps you determine how much to charge, manage your time, and identify the tools and helpers you need to be successful. It’s also a major confidence boost to know what the next step will be, and to be able to communicate that to clients.

Have a cushion and a backup plan that you can implement within 30 days.

Side hustling is really hard. There will almost certainly come a point where you have to drop your safety net in order to realize your full potential. But don’t let it go too early, if at all possible. Build your savings and build your plan before you take the plunge. Don’t quit your day job yet, and don’t burn the bridges leading to your backup plans. I renewed my teaching license last year knowing that if I ever need to, I can get into a substitute teaching pool pretty quickly. My resume is up to date and I haven’t ditched all of my business casual wardrobe even though I’m getting damn tired of hauling it around.

Don’t spend time or money you don’t need to yet.

One of the items on my death list was the business becoming a money pit. Fortunately, blogging, copywriting, and web design has pretty low overhead: computer and Wi-fi. (I also use Adobe Creative Cloud for my design work.) I think one of the biggest temptations entrepreneurs have to face regularly is trying to buy a feeling of legitimacy by spending money on fancy websites, professional branding, and custom logos. Keep in mind that I make fancy functional websites, professional branding, and custom logos, so I’m not saying those things aren’t important or useful. But you don’t need all of that right out of the gate. Get a workable process for providing a viable product/service and an excellent customer experience first.

Invest in things that will save you time and energy.

I know I just said not to spend money you don’t have to. On the other side of the coin, though, there are products and services you can pay for that will save time, energy, and maybe even money.

The first thing I invested in was business coaching, which was worth every penny for the bulletproof working process I had at the end of it. The next thing I paid for was a subscription to Dubsado, which is a web-based customer relationship management (CRM) software. Admittedly, I probably only use about 40% of its features, but sending proposals, questionnaires, and proposals makes me money, so it’s well worth the monthly subscription fee. (They also have yearly and lifetime options. You can get 20% off your first month with my code: aminusmama.) I am probably going to start hiring a cleaning service to give me back several hours of my week which I can then use to pick up more projects, or do things that make me a happier, healthier human being.

It’s a delicate balance between not spending more than you have to and investing in tools that will help you grow. That balance looks different for everyone, so go back to your goals and values to help determine what will be most helpful for you.

Get help if you need it.

Hiring employees or outsourcing certain business tasks may seem like an unbearably decadent expenditure, but sometimes the time savings and return on investment are well worth it. I worked as an assistant in the real estate industry, and all of my employers said that my service enabled them to do more business. If paying someone $15/hour to respond to emails allows you to go out and sell houses or coach executives or build websites and make $50 or $500/hour, that’s money well spent. If you can pay someone to write your website copy (heeeeyyy!) instead of banging your head on the keyboard for 6 hours and procrastinating for 3 months, it might be worth finding someone to help you.

Getting help doesn’t always mean an ongoing expense. Take a photography class and learn to shoot your own products. Hire a consultant to help set up your ledgers and teach you basic bookkeeping. Find a copywriter to help you develop your brand voice or a designer to tweak your existing visual brand. (Hello!)

Assess constantly and hold everything lightly.

From my teaching days, I learned the importance of constant assessment. No, I don’t mean standardized testing. I mean checking in with whether my students truly understand what they were learning, and adjusting my teaching (sometimes VERY quickly) when things weren’t clicking. As a business owner, it’s critical to keep tabs on what’s working and what isn’t. Keeping a light grasp on what I think my business “should” do or have or look like allows me to cut bait on ideas and expenses that aren’t bringing a good return. Admittedly, I can sometimes be overly lean and mean about trimming costs and dumping ideas that aren’t viable immediately, so again it’s about balancing expenses now and potential efficiency gains or return on investment later.

Stay in your lane…but don’t be afraid to take profitable detours

I joined several online communities for writers and freelancers, and many of the writers in those groups seem to focus on more traditional publishing models, i.e. pitching and getting placed in periodicals and large websites. I started feeling some major imposter syndrome about my lack of bylines in The New York Times until I realized that few, if any, of my small business clients cared about my publishing record. They wanted to know how I was going to take care of them. Period, full stop. And that’s what I’m choosing to focus on, though for personal gratification I also work on getting published on external platforms.

There’s a lot of conflicting advice about when, how, or even if to narrow down to a specific niche. When I first set up my business plan, my intended niche was mompreneurs with established businesses. Guess how many of those I had when I started out? Actually, my first blogging client was a doula agency, BUT I also worked for educational startups, companies that sold water testing kits, and research scientists. Were any of them my “ideal” client? No, but they were willing to work on the terms I set forth (read: pay me well for my time) and gave me constructive feedback and valuable work samples. While I concentrate on writing for small businesses, I keep my eyes open for any opportunity that might be interesting and lucrative.

Embrace humility and “good enough.”

My final piece of advice kind of circles back to my first point, as well as my revised beliefs about Calling. I used to think that I had to do something big and fancy to please God, and then I thought I had to do something big and fancy to please other people. I thought I was going to be the next Good Will Hunting, then the next Preston Bailey, then the next Bambi Cantrell. Not surprisingly, reality didn’t meet those expectations.

My aspirations are much humbler now: be well, do good work, keep in touch. Five years ago, lowering my expectations felt like a cop-out. But honestly, life is way more fulfilling now than five years ago. I don’t need to make six-figures or have thousands of social media followers or be a bestselling author on Amazon. I need to do quality, creatively fulfilling work, keep my own flexible schedule, and make enough money to care for my family. Those goals are the only things about my business that are set in stone, and they’re the only ones that need to be.

What are the goals and values that allow you to be fearless in your business?
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