This is a guest post from Location Rebel Academy member Allison Troutner.
When Sean asked me if I would like to be interviewed about my path to freelance success, I started thinking about what got me from A to B.
Looking back, my success comes down to 4 things that allowed me to grow quickly. They involve a refrigerator, a trampoline, knowing very little, and most importantly just doing something.
No, this isn’t an “I made a six-figure business in four months story.”
This is an “I’m a badass who built a business in time, using my strengths, and honoring the process story.”
By doing this, I have clients I enjoy working with, I am making more per hour than any job I’ve had before, and I have flexibility built around what’s most important to me— my family (and exercising and eating and sleeping).
After 7 months working only 1-3 days a week, I’ve earned secured contracts worth over $13,000.
I’m sharing these tips with you because I want you to know it’s possible to build your freelance writing career in a way that feels genuine and on your terms. It’s so easy to be swept up in the momentum of the freelance grind, but there’s a lot more at stake than just earning money fast.
Go too hard too fast, without proper support and you’ll burn out. Spend too much time researching instead of ‘doing’, you’ll flounder like a fish out of water.
So how will a fridge, a trampoline, and knowing very little help you build a successful freelance career? I’ll tell you.
1. Know Your Why and Stick it on Your Fridge
What separates us from animals is our ability to reason, to find purpose in chaos. To not simply survive, but live.
This is your WHY.
Your why has to be big and I don’t mean vague. I mean it has to be true to your core. If at any point your “why” leaves the room, you feel empty, lacking.
I know for a lot of aspiring freelancers, their Why is often motivated by money. I need more, want more.
Must. Have. MORE.
But if you analyze those thoughts more closely, you’ll find you’re not motivated by money, but by what type of lifestyle it provides.
Philosopher Frederick Nietzsche said, ‘He who has a why can endure any how.’
The business of freelance writing isn’t easy. You will experience low points: criticism, writer’s block, and paid work droughts. Your Why will help you get through the mud of it all. But if your Why is purely financial, you’ll find it hard to justify the work you’re putting in.
“A clear sense of purpose enables you to focus your efforts on what matters most, compelling you to take risks and push forward regardless of the odds or obstacles.” — Dr. Margie Warrell
If you’re having trouble nailing down your Why, try going through these four questions:
1. What makes you come alive?
2. What are your innate strengths?
3. Where do you add your greatest value?
4. How will you measure your life?
Our why probably does involve money on some level, but it goes deeper.
For instance, my Why is:
“I must have a flexible lifestyle where I can work around my kids’ school schedules, doctor’s appointments, and family vacations. That we can meet the needs of that lifestyle including paying our bills, saving for emergencies, and earning disposable income for vacation and opportunities that will allow my children to grow as people through cultural experiences.
Having a flexible lifestyle will allow me to be close with my husband and have fun (dancing, drinks, date nights), and be there for my kids when they need me, at the drop of a hat, without requesting PTO or asking a boss.
The only career I can tolerate at this point is where my work + life is balanced to satisfaction.”
You’ll notice that my Why includes money “paying for bills, going on vacations” AND it includes the reason for those financial standards “so my kids can have experiences and my husband and I can go on dates.”
This is what I remind myself daily, especially when I get negative feedback, or I go a few weeks without a positive lead for new work. Failing or quitting is not a choice here because my Why is more important than my fear of failure. It’s more important than simple financial growth.
If it was only about money, I could’ve worked up to a CFO position at a previous employer. I chose not to because it didn’t meet the needs of my lifestyle and certainly was not how I wanted to measure my life.
Grab a fridge and post your Why: Take several minutes, and write down your Why.
Put it on the fridge, or bathroom mirror, computer monitor, coffee carafe. After a few weeks, you’ll notice it becomes your default mantra. I’ve found that when I start to doubt myself, my mantra just pops in and says “hello, don’t forget about me!”
Right. Hi. Okay, let’s keep going.
2. Build Your Support System like a Trampoline, You can Fall Without Hitting The Bottom (and it should include more than your mom).
Build up a support system and you’ll find that when the going gets tough, your support system is like a trampoline that keeps you from hitting rock bottom. They can’t climb the mountain for you, but they’ll bounce you back up with a little more oomph in your step.
Yes, it can be your mom, but more importantly, it should be multiple people who want to see you succeed and are willing to help in any way they can: from providing childcare, mentorship to therapy.
I know, it’s awkward to tell people about your business.
Do you know what’s more awkward? Hiding your business, then telling people it failed and hearing them say, “Wow, I wish you would’ve told me. I would’ve loved to help.”
Think about an entrepreneur you respect. How do you think they got to where they are? Alone? No, they had support from family, spouses, mentors, and investors.
- Nick Goodman, the guy who founded GoPro sold bead and shell beads out of his VW van and moved in with his parents at the age of 26 to save money and fund his idea (no, I’m not suggesting you move in with mom).
- Madam C.J. Walker, reputed to be America’s first self-made female millionaire, learned the art of business and entrepreneurship from another female entrepreneur. As she grew her own business, her husband helped her sell her products door to door.
- Bill Gates had a mentor, Warren Buffet, whom he gives credit for “teaching him how to deal with tough situations and how to think long-term.”
The point is that there’s a lot more to building a business than money or time.
You need people who can help take over household tasks or childcare while you spend time growing your business, especially if it’s not your full-time gig. You may just need someone who believes in you when it gets hard because it will get hard.
One of the very first pieces of advice I received from my mentor was to make sure my partner was on board. I was surprised by her urgency on this point. I already knew my husband was supportive of my writing career, but I didn’t realize how comprehensive his support would need to be.
To meet deadlines, I needed him to watch the kids in the evenings, do bedtime routines solo, or even take them for a day on the weekend. If he wasn’t invested, my business wasn’t going to work. He had to understand the value of my business as much as I did, or else it would’ve driven a wedge between us.
Build Your Trampoline: Make a list of the support you need to fall back on when building your business. Do this and you’ll never hit rock bottom.
Here’s what my support system looks like and how it helps me:
- Childcare/babysitter (or your dog walker): I don’t know about you but I can’t work when I have grubby little paws (of any species) begging at my leg at all hours. Give yourself some space!
- Partner/spouse/roomie: Delegate tasks. My husband always does the laundry and takes the kids in the evening or weekend hours when I need to work.
- Find a mentor(s): I talk about this in detail in my word-of-mouth marketing article. Bringing other people into your business who have experience can increase the rate of your growth exponentially. My mentor got me my first paid gigs and from that point on, I’ve grown much faster. I found my mentor by typing in “freelance writer + my city + niche.”
- LRA Writing Community: Need a pick me up or some advice? Every single person in the LRA community is in the trenches with you. Whether it’s sharing leads, swapping stories, or just venting about the process, my accountability group and the forums have been a massive resource for my business growth.
- Friends & family: I told friends and family that I trust. They listen and hand over leads when they come across them. If I need someone to watch the kids, they’ve been happy to help. When I just want someone to say “Wow, you’re doing amazing!” I can *usually* count on them.
- Therapist: For the times when you need an objective third party to hear you out, get a therapist. I’ve seen a therapist for more than ten years. Having a professional who can give you a birds-eye view of things can help you keep your goals in focus and offer actionable tools for coping with stress and change, which are frequent aggravators in entrepreneurship.
- Hobby: I joined a local bouldering gym that’s mission is to create a social fitness community. I can climb with friends, grab a beer, and recharge. No burnout out here!
If you try to build your business alone, you are actively working against yourself. Don’t do that, please.
Because I built this support system, not only do I have cheerleaders, I have people who are invested in my growth and want to see me succeed as much as I want to be successful.
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3. Not only should you not try to learn everything before you start, but you should also expect to know very little.
The most efficient use of your time as a new freelancer is to learn as you go. Yes, have a basic understanding of the industry. But if you learn as you go, you will earn money and build your business at the same time, instead of trying to learn everything before you start and then realizing that a lot of what you learn is not playing out in reality.
I stunted my growth in the early weeks because I tried to read, learn, and understand everything before I took one step. You will learn some things, but every client is different, every industry is different. I’ve learned so much by doing— working things out in real-time.
The best part of the LRA 12-week freelance writer boot camp is that it progresses with you. One week at a time. This may be the most confusing sentence you read all day, but it’s one of the truest things I’ve learned in this career: “You will only figure out what you need to know when you realize you don’t know it.”
Most people just say “You don’t know what you don’t know.” What I mean is, especially if you’ve never written professionally before, you will learn by doing.
You won’t know that you want to add social media campaigns to your skillset until a client asks you about it in an interview and is willing to pay you well for it.
Don’t Overthink Your Niche
In the first month or so of joining LRA, I waffled over my niche(s) obsessively. I had work experience and hobbies, but nothing that I felt I wanted to write about regularly.
Weeks wasted my life.
I finally decided to market myself as a content writer and picked three very general topics that I found mildly interesting and I had a little professional experience: finance, health, and EdTech. I wrote samples and put them on my site.
Do you want to know what I write about now? Cannabis, cyber tech and cybersecurity, music, fashion, financial advising, and writing.
I don’t just do content writing either, I do a lot of copywriting which was not a skill I thought I would gain this early in my career. Again, you don’t know what you don’t know. You just have to write around and see what sticks.
No, you don’t have to be an expert. I started (and still am) a bit of a generalist. This works for me because I have a background in research and love to learn. It’s a great combination.
Sean says, “Most generalists also have one killer skillset: they are awesome at research. So if you’re someone who loves learning tons of new information quickly, being a generalist might fit in with your interests.”
I’m not an expert and I don’t have to be. I just have to learn enough to be helpful and be willing to put in the effort. Expertise comes with time.
For more about this, watch this video about “relative expertise.”
Bonus Tip: Do what you can, when you can
If you’ve heard anything about starting a writing career you’ve heard you need to “write every day.” If you have the self-discipline and lifestyle to do that, you should because it is helpful.
But when I started I was home full-time with two kids during a pandemic. This meant that I was working during erratic nap times before kids woke up in the morning (5:00 am) or in the evenings (8:30 pm). That’s a rough schedule to write every day.
I couldn’t work that often in the mornings or the evenings because I was tired. Utterly wiped. Not to mention, I missed my husband.
So on the days when I could work, I didn’t always want to write. I was still motivated by my mood as opposed to habit, still exercising my writing muscles. My alternative was just to do something every day.
On the days when the writing wasn’t coming, I would:
- Pop on Twitter or Linked IN and start following industry leaders or prospective clients.
- Lookup a writer whose career was admirable and sign up for their email list or newsletter
- Read a chapter out of a content writing book, like Jennifer Goforth Gregory’s book
- Jumping on the LRA forums
- Add one new contact to the list of prospects
- Message your accountability group
- Find a well-written article on Medium or national publication and study it
Important caveat: It’s very easy to get stuck here, not writing. But I bring it up because it’s important to honor any momentum. All of those resources come with tips, tricks, and quotes that I logged away in my brain and I still draw from to this day.
For me, I had to write at my own pace, but by doing something most days, I kept that energy going.
And then here’s what happened: I started to crave writing.
I was inspired by clients I was finding, eager to email them, or motivated by the success of other writers. Then I started to write more, a few times a week. As the work came in, 5 days a week.
Now I’m posting at least a tweet a day (even just a retweet) and working towards a more robust daily writing habit.
Create Space for Luck To Exist
Another way to think of it is that each day you put energy into your career, you are creating space for it to grow.
Here’s a piece of wisdom I gleaned from Seth Godin: You can create space for luck to exist.
If you send one email, that might be the email that gets you a huge breakthrough gig.
For me, it was a Facebook post my friend sent me from a private group she belonged to. It ended up getting me a gig with an IT agency with a contract worth more than $10,000.
I put in the effort to talk to my friend about my work, followed through on the lead with an LOI, interview, and writing a sample. It was a combination of putting in the energy so that luck ( i.e. the client) could find me.
“Luck is a tactic. An unpredictable one, sure, but if it works, it works. A useful strategy might be: I’m going to establish a pattern of resilience and apply information and testing to discover what works. And one of the tactics to support that strategy could be showing up in places where luck can help me out. If I can persist long enough, I’ll get lucky.” — Seth Godin
Don’t let inexperience or feeling of failure keep you from doing what you love.
Yes, you will embarrass yourself. Say it with me, “I will embarrass myself.”
Good. Now, pour a glass of wine or mix one of Sean’s cocktails (Aperol Spritz is my summer go-to) and get out there.
If you’ve got a fridge, a trampoline of support, and a willingness to learn, you are well on your way to building a career you love that you can do from your bed, while holding your sleeping baby, or on a breezy porch with a fresh-squeezed lemonade. Pick your pleasure — I did.
We’re a community: Follow me on LinkedIn, Twitter, or Medium. I can’t wait to hear about how your business is growing similarly, or completely different than mine.
Allison Troutner is a freelance content marketing writer in Indianapolis, IN. She writes all things women’s health & technology, the arts, and personal finance. The things that make her tick include her two toddlers, fantasy fiction, and coffee in excess.
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