Popping in today to share a few lessons learned from my nine years as a full-time freelance writer.
These insights are useful to anyone running a business. I wish I would've known these things...well...nine years ago.
I’ve also added in relevant podcast episodes where there’s more detail on these specific points.
Let’s get to it.
1. Ask for help when you need it.
Freelance writers have to keep a lot of their own plates spinning, but that doesn’t mean they have to do everything by themselves. Asking for help and outsourcing tasks that make you frustrated will free up your mental bandwidth to focus on what you’re good at.
For me, outsourcing my retirement investing, taxes, accounting, and bookkeeping was a game-changer. I hated managing these aspects of my business, so I handed them off to folks who are specialists in these areas.
It came with a small price tag, but the peace-of-mind it provides is more than worth it. If there are areas in your business you need help with, find out who can help you and hire them to do so.
2. Start building an audience as soon as possible.
When the day comes that you finally want to start branching out beyond client work and leveraging your expertise in the form of consulting or products, you’ll need a relevant audience to share those with. That’s why it’s important to start working on growing that audience sooner rather than later.
This might be through an email list, your social following, a podcast; the medium is up to you. Just start sharing valuable lessons you’re learning as you go and let folks behind the curtain of your business. Bring them along on the journey with you.
3. Teach everything you know.
This phrase is one I swiped from Convertkit, but it applies to freelance writers, too. There’s no real guidebook for how to launch and run a successful freelance business, so teaching lessons learned through trial and error helps position you as an authority in the space and a go-to source of knowledge in your area of focus.
This approach has been the foundation of resources like my newsletter and digital products. Some freelancers worry that sharing their knowledge means other writers will take away from their business opportunities, but the truth is: Even if you share your “secret sauce,” no one will ever be able to replicate the exact experience and results you deliver as a professional.
Spread the wealth when it comes to your knowledge. There’s only an upside.
Get past those fears and find a way to sell that feels natural to you. Forgo the tactics that make you cringe, and constantly experiment and ask for feedback on how you can improve your approach. That along will separate you from the masses.
6. Beware of burnout.
Working too hard for too long is a recipe for disaster. Freelance writers don’t have an overarching supervisor or boss figure to remind them to take time off from time to time, so it’s easy to slip into the “always on” mentality. When this happens, not only does the work become less fulfilling, but you will also eventually start to resent it, too.
It’s important to have an accountability partner who can check in on you and keep you aware of when you’re showing signs of burnout. When the red flags pop up, give yourself permission to step away and take a break. You need a mental reset so you can come back fresh.
7. You don’t always have to love the work you’re doing.
Speaking of resenting your work: The reality is that you’re not always going to love the work you do.
Sometimes it’s a slog; sometimes it’s difficult. No one loves their work 100% of the time. It’s normal to feel unmotivated/uninspired from time to time.
This is why I’m a huge proponent of having creative side projects that help keep your brain sharp and engaged in different ways.
8. Creative side projects keep your brain stretchy.
Don’t lose sight of whatever your creative side project is, whether it’s painting, making YouTube videos, novel-writing…you name it.
These outlets can be your saving grace when you need to shift your mental energy and focus. Plus: They’re great mental gymnastics that can help you better execute your day-to-day client work, too.
It’s tempting to just veg out in front of the TV at the end of the day (and we all need that sometimes!) but it’s also important to have a just-for-fun project you can channel your imagination into as well.
9. Having a large online following comes at a cost.
It wasn’t until the past year or two that I started amassing a fairly large following online, mostly on Twitter. Having an ever-growing audience of folks who want to hear from me is great, but it also comes with some trade-offs.
The larger the audience, the more people there are to notice when you mess up, to criticize, etc. I’ve been fortunate to have 99% positive interactions so far, but there is the occasional troll with a M.O. of making me feel small, or stupid, or wrong.
It’s part of it, and I just do my best to ignore non-constructive criticism, but it does take its toll.
10. You don’t have to out-earn yourself month-over-month.
As a freelancer, the amount you earn each month is really up to you based on how much you’re willing to take on. That’s a fantastic possibility for the self-motivated, highly efficient folks out there, but it’s also dangerous, as it can set them up to be overly competitive with yourself to the point of burnout.
From experience, I can tell you that having an ever-rising benchmark for “success” is a recipe for disaster. Instead, focus on maintaining a workload that’s manageable and realistic for you.
11. Rejection and mistakes happen. How you deal with them is more important.
Your proposals and pitches will get rejected on a regular basis. You will, at some point, make an error within your work. All of these things feel bad; sometimes they even make us think, “Man, I’m not good at this. I should just give up!”
The reality, however, is that to get rejected and to mess up is to be human. It happens to all of us. The real issue of importance here is how you handle these negative experiences. Are you learning from them? Did you handle them proactively, professionally, and with grace?
Less-than-stellar experiences are powerful teaching moments. Don’t get stuck on the downside; turn them into another stepping stone along your journey.
12. It’s okay to call yourself a freelancer.
“Freelancer” often has negative associations that come with it: It’s something people do in-between jobs; it’s not a long-term, sustainable career path; people who do it are just scraping by. However, in my experience, none of these statements are true.
Sure, I could call myself a consultant, or use a brand name to market my services, or I could make up some fancy-sounding title for myself. But you know what? The easiest, clearest way to explain what I do is to use my name, face, and the “freelance writer” title to explain who I am and what I do. There’s no shame in calling yourself a freelancer.
Leave the negative associations behind and let your track record of success speak for you; not your title.
13. Every freelance writer needs a sounding board.
Working alone as a freelancer means most of the time there’s no one around to bounce ideas off. It’s just you. On days when you feel lost, or need to troubleshoot, or just want to vent, it’s important to have an outlet for that.
For some, working with a paid coach or mentor offers this plus the added benefits of accountability check-ins, guidance, and structure (like regular meetings.) For others, however, having a fellow freelancer friend does the trick.
Regardless of the route you choose, remember: You don’t have to do this alone. Make sure you have people you can call on for support.
14. Focus is an underrated skill.
Your attention can easily get stretched thin as you explore different projects, products, and ideas as a freelancer. However, when you split your attention in this way, it quickly becomes difficult to lean into any one particular area.
You can go wide or deep; not both.
Rather than keeping a lot of plates spinning, I’ve learned the returns are higher when you focus on just a few things (and doing them really well.) Focus is an underrated skill that can be a determining factor when it comes to long-term sustainability within a freelance career.
15. Celebrate your wins (no one else will do it for you.)
One of the biggest things I’ve missed since leaving the traditional office work environment is having co-workers to celebrate things with when things go well. I missed having work friends who can take you out to lunch on a good day or the boss who says “Well done” when you’ve accomplished something important. I realized that when you work independently, you have to do that for yourself.
That’s why I do an annual “year in review” post and try to do something fun on my “freelance-iversary” each year. No one else will do it for you, so it’s important to take time to celebrate accomplishments in your own way. Don’t let your big milestones quietly slip by.
16. Recurring work and long-term relationships = business longevity.
It’s much easier to keep working with clients who already know, trust, and like you than it is to sell yourself to a brand new client every time you need work. That means it’s crucial to develop deep, long-term relationships with the clients you want to work with regularly.
To accomplish this, I make a point to send them handwritten thank you notes, to regularly check in and see if there’s anything I can help them with, to ask questions like: “What can I do that would make your work easier?”, and to send small thank you gifts during the holidays. These small actions and gestures go a long way and help you stand out from the masses.
17. Form healthy workday habits and become a slave to them.
Okay, so I adapted this line from Matthew McConaughey’s book Greenlights, but I love the message. When you’re busy, it’s easy to sit at your desk all day, to skip lunch, to subsist on caffeine, and to hunch over your keyboard until it’s dark outside.
But guess what? Your body and mind will eventually revolt. Instead, be proactive about forming healthy workday habits (like getting up and going for a walk, doing yoga/meditation, drinking plenty of water, taking an *actual* lunch break, etc.) If you don’t, you’ll find yourself in a world of hurt.
18. Not everyone needs a schtick or “alter ego” for the sake of branding.
Lots of writers decide to create some sort of marketing gimmick or “alter ego” for themselves as part of their branding. For some, it’s great. For others, it’s noise that’s only getting in the way of the skills and services they’re selling.
Ask yourself: Is this really helping me sell? Or is it unnecessary? Talk to people who’ve hired you in the past and get their perspective on it; don’t guess. I’ve opted to just market my services using my name and face, and I’ve had no problem growing my business that way. It’s a personal choice at the end of the day, but it’s one to think about seriously.
19. Don’t be afraid to take the lead with clients.
Early in my freelance career, I always felt unsure of what *exactly* I was supposed to be doing, so I deferred to my clients when it came to processes and workflows. This meant I was at the mercy of learning various softwares, approval processes, etc. (which meant the work took longer.)
As I got more experienced, however, I figured out my own processes that were often more efficient and effective, so I started taking the lead on projects and laying out my workflow in a proactive way. So often clients were grateful to have an experienced professional take the lead, and more often than not, it got me hired, as it proved I knew my way around the work I was doing.
The sooner you do this in your business (and templatize much of your documentation), the faster you’ll be seen as a professional your clients can trust and defer to when it comes to project execution.
20. Raise your hand and say so when you have a good idea.
Speak up! All of the best opportunities I’ve had so far have come from speaking up and saying so when I’ve had a good idea or seen a problem I can solve. It’s easy to sit on the sidelines, and speaking up/putting yourself out there is risky, but what’s the worst that can happen?
You’ll get a “no.” And then you try again. When you see a need you can address, be sure to position it in the right way and focus on providing value to the person you’re pitching the idea to.
My go-to formula: “I think you could do X thing and produce Y result, and here’s exactly how I can help you do that via A, B, and C.”
21. Always be connecting.
Everyone loves a good connector, don’t they?
They generate so much goodwill and positive ripple effects. I’m always working to refer smart people, to connect folks on Twitter, and introduce people I think should know each other.
By doing this, the favor is often returned, and you become known as one of those highly valuable, well-connected people. You lose nothing by making these connections: It’s pure gain on all sides. (Just make sure everyone’s okay with you making introductions beforehand!)
22. Keep an eye out for clients who exhibit red flag behavior.
If you notice a client doing things that make you feel uncertain during your initial interactions, don’t let things get too far (and definitely don’t sign any long-term agreements with a client until you’re sure you work well together.)
Red flags are things like: Not respecting your office hours, telling you how the work should be done and when, missing deadlines or phone calls, etc.
Be clear about your expectations and work boundaries right from the start, and if they’re crossed, address the issues as soon as possible. If things go unresolved, you can respectfully end the working relationship and wind things down with your client. Be sure there is a section in your contract that outlines this as well.
23. Curiosity is a secret weapon.
Not only will a curious mind help keep your skills and mind sharp, but it’ll help you be a better writer, too. Curious people always ask, “But, why?” and answer those questions within their writing, which means they can go deep and write things that are valuable and relevant for a long time.
Plus: You never know where your curiosity will lead. When you follow it, it may open doors to new career paths, connections, and friendships.
Example: I’m fascinated by quantum mechanics, and a friend on Twitter who’s also curious about it has made some excellent book recommendations for me on that topic this year.
Those initial conversations eventually lead to work opportunities as we got to know each other better. Win-win!
24. Twitter opens more doors than you could ever imagine.
If there’s one social media platform that’s paid back dividends when it comes to investing time and energy there, it’s Twitter. Twitter offers a direct line of communication with potential clients, writers, editors, and smart people you want to know (and you can hop into lots of conversations already happening there.)
The thing to remember: It’s a cocktail party; act accordingly. People are watching and listening. Approach it not with a “what’s in it for me?” mentality, but with the goal of making new online friends, learning from experts, and participating in interesting exchanges. The more connections you build there, the more doors will open for you.
25. Goals are great, but only if they’re realistic.
The easiest way to set yourself up for failure is to get the bar too high for yourself. Don’t set crazy revenue or output goals, for example. If you’re an overachiever, you’ll break yourself trying to meet an unrealistic objective (and you’ll be mad at yourself when you fall short.)
Instead, opt for tiny wins that you can accomplish without overextending yourself. Those small steps of progress add up, and while they don’t have the big payoff that comes with accomplishing some near-impossible feat, they’ll help you make meaningful progress while maintaining your sanity.
26. Fancy tools and software aren’t always the secrets to better writing.
You can have the best toolkit on the market, but the reality is: The only way to truly improve your writing is to practice.
Sometimes those tools only even get in the way and make things more complex than they need to be. Don’t be seduced by fancy software that claims it’ll revolutionize your writing abilities; that’s just marketing. You are the key to better writing.
Establish a regular writing practice, read as much as you can, and keep at it. Tools aren’t the answer. You can waste a lot of money learning that the hard way.
27. You do not need to say yes to every call request, podcast interview, or guest post opportunity that comes your way.
Time is a limited resource, and you have to be protective of it. Be wary of things that can easily eat up your time for very little return on investment. Consider the potential returns that can come from various requests of your time (like podcast appearances, speaking opps, etc.), and make sure the upside is worthwhile.
After all, the more you say yes to these, the less time you have for billable working hours. Follow the rule of “If it’s not a hell yes, it’s a no” as a guideline.
28. Freelancing is 100% a lucrative, full-time career path.
There seems to be a generalization out there that freelancing isn’t a lucrative full-time career path, but the fact is: It very much can be.
Not everyone is going to reach the six-figure mark, but the motivated have an opportunity to earn more than they would with a set salary. And yes, freelancing is not for everyone: It’s best suited to self-starters who aren’t prone to procrastination and that do well with working independently.
Overall, don’t believe the naysayers. With remote work on the rise, freelancing is only going to become more popular and “normal” as a profitable, long-term career path.
29. Define what “enough” means to you within your business.
Because freelancing tends to be more open-ended (no set salary, create your own office hours, etc.) it’s easy to fall into a trap of self-competition. It’s important to define what qualifies as “enough” within your business.
Answer questions like:
How many hours do I want to work each week?
How much do I want to earn each month/year?
Once you’ve hit (or neared) your goals, you can give yourself permission to slow things down, take time off, and enjoy the flexibility freelancing provides. Without those benchmarks, though, you can easily form some workaholic, always-on, “never enough” tendencies which are a recipe for burnout and unhappiness.
30. Stay connected and don’t self-isolate.
Working alone and from home is naturally isolating in nature: There are no co-workers, no office holiday parties, etc. It’s important to be aware of this and to work hard to stay connected, both online and off, through things like virtual coffee dates, attending conferences, taking retreats with fellow freelancers, etc.
Being social is a skill, and when you fall out of practice, it becomes difficult (which will have a ripple effect into your client interactions.) Keep yourself rooted in a network of friends, peers, and like-minded people who understand your work and lifestyle. Find your tribe.
31. Automate tedious tasks to work smarter, not harder.
As a one-person operation, you have a lot on your plate (and your time is money.) Automate as much as you can to work at maximum efficiency with help from software, templatizing documents you use over and over, and creating easy-to-customize scripts for common conversations.
If needed, hire help! The apprentice model works great for this.
Prioritize your efforts by figuring out what you spend the most time on (or repeat most often) and work your way down the list.
32. Always get a signed contract before work begins.
It’s hard to do things like enforce boundaries and battle scope creep if both parties don’t sign off on a legal agreement before working together where all of this is defined.
In your contract, be clear about your payment expectations/process, your workflow, the project requirements, and the timeline. There are many templates out there you can purchase and then customize for each new client. Don’t skip this step.
33. Every new client should pay an up-front deposit.
For new clients you haven’t worked with before, it’s important to get a deposit paid before work begins as part of your onboarding process. This can range between 25-50%, but should be collected before work begins as a show of good faith. This also helps the client put some “skin in the game” by investing in your work at the start of the working relationship.
It’s also a fail-safe so you aren’t left empty-handed if a client falls off the face of the earth mid-project. Be clear about when the remainder of the deposit fee is due as well.
34. Learn how to handle edits with grace.
Working with editors is a regular part of a freelance writer’s job. It’s just part and parcel.
99% of the time, editors deliver notes and edit requests aimed at improving the writing. It’s not a personal attack, so don’t take edits personally. Know how to ask for helpful feedback and add clarity if you feel confused about an editor’s requests.
Also: Be clear about how many rounds of edits are included with your rates (so things don’t get out of hand.)
35. Charge what you’re worth.
Guess what? You should probably charge more.
If you have a solid track record of successes, are in high demand, and consistently do what you say you’re going to do (on time!) then you’re ahead of the pack. Know your value and charge accordingly…and raise your rates on a regular basis.
What would you add?
I’d love to hear from fellow writers and see what lessons you’d add to this list. Tweet me @kaleighf.
