How to Start Freelancing: Do's and Don't's
Tips from other experienced freelancers on what works - and what doesn't.
Picture this: It's 2022, I'm sitting in my home office, burnt out to a crisp at my agency job, when something inside me snaps. Two weeks later, I hand in my notice. Two months after that, I give up the full-time job search and start freelancing without a single client lined up.
Was it reckless? Absolutely. Did it work out? Eventually — but not before I learned some hard lessons about what it really takes to make it out here as a freelancer.
Here's the thing about YOLO-ing your way into freelancing: it's equal parts terrifying and liberating. While I don't necessarily recommend my particular brand of diving into the deep end, I can share what I learned from taking the plunge, as well as some thoughts from some colleagues from TOFU — a content marketing Slack group that I highly recommend.
Whether you're planning a more calculated transition or feeling that same burnout-induced restlessness I did, these insights might help you avoid some of the mistakes I made along the way.
The Do's: What Actually Works
Do: Build Your Emergency Fund First
You know in horror movies when someone says "I've got a bad feeling about this" right before everything goes sideways? That's what starting freelancing without deep savings feels like. I learned this the hard way when my first famine season hit and I had to dip into my emergency savings for an extra $2000 to cover my mortgage. (Thank goodness I had savings.)
Trust me, you want at least three to six months of expenses saved up — even if you think you've got work lined up. Maybe even more than that.
Do: Start With Your Network
One of my first closed deals came from a former client from my agency job. I'd almost talked myself out of messaging her because I was worried that she didn’t like working with me. But lo and behold, she did. That project ended up covering two months of bills.
The lesson? Your network is bigger than you think, and people generally want to help if they can.
Do: Build a Pipeline Early
Here’s a hard truth: freelancing is feast or famine. One month, you’ll be drowning in work; the next, your inbox will be a ghost town. The key to stability? Consistent outreach.
Make it a habit to pitch new clients, even when you’re busy. Use LinkedIn, email, or whatever platform your ideal clients hang out on. Keeping your pipeline full makes sure you’re not panicking during slow months. (Ask me how I know about this…)
Do: Charge What You’re Worth
Pricing your services is one of the hardest parts of freelancing. But here’s the thing: if you don’t value your work, neither will your clients. Do some research on market rates for your industry, set a baseline, and stick to it. Over time, adjust based on demand and the value you bring due to your expertise.
Pro Tip: Factor in More Than Just Your Time
Remember, freelancing comes with overhead: taxes, health insurance, software subscriptions, and more. Your rates should cover all of these expenses, plus a profit margin that makes the leap worthwhile.
Do: Find a Great Tax Pro
Full confession: I still don't have a tax professional, and every quarter when I'm calculating my estimated taxes, I deeply regret this decision. Those self-employment taxes aren't going to figure themselves out, and let me tell you — trying to learn the tax code through trial and error isn't an adventure I'd recommend.
Do as I say, not as I do: get yourself a good accountant who knows freelance businesses inside and out.
Do: Learn to Be Tenacious
Freelancing isn't always about who's the most talented — sometimes it's about who sticks around the longest. Shannon Clark puts it perfectly: "Play the long game. There are no magic beans, wish-granting genies, or perfect clients, but there is a silver lining if you're willing to stay in the game and allow yourself to grow in the process."
This resilience extends to handling feedback too. As Imogen Sharma notes, "Do have a thick skin. You'll face rejection and criticism sometimes, it's part of the process. Don't take it personally, learn from it, grow from it, and keep moving forward."
Do: Work On Your Portfolio
“Work on your portfolio right from the get go. Don't get swamped with client work to the extent of leaving behind working for yourself through your portfolio building,” says Deborah Oyewole. “The portfolio doesn't have to be complicated, just an online space to showcase your work.”
Hsing Tseng
I spent hours perfecting my portfolio website when I first started freelancing, and I believe that effort paid off in terms of my inquiry to client conversion rate. But you don't need anything fancy — even a basic Notion page or carefully curated Google Doc can work.
Do: Request Testimonials
Speaking of portfolios — they're even better with social proof. As Deborah admits, "I regret not knowing this as one of freelancers' tools early enough." She recommends asking for testimonials as soon as projects wrap up. I personally ask for them at the 6-month mark or so — when the timing feels right. I currently use Senja (affiliate link) to do so, and it’s been a great experience for both me and my clients to use.
Pro tip: Keep a "praise" swipe file in your Google Drive or Notion where you save nice feedback from clients, even the casual "thank you, this is exactly what we needed" messages. These make great social proof for your portfolio and proposals, and they're excellent mood boosters during those inevitable imposter syndrome moments.
Do: Find Community
My first year of freelancing, I tried to figure everything out alone because I thought asking for help meant I wasn't cut out for this. Now I know better.
Faith Foushee, freelance writer, shares: "Genuinely investing your time in others and building relationships is always worth it. You never know what a conversation might lead to. Whether it be now or years from now, it all starts with one conversation."
She's right. Several of my current clients came through other freelancers who were too busy to take on new work. I've found my people in Slack communities and LinkedIn connections. These bonds aren’t just about finding work — they're about having someone to bounce ideas off of, share wins with, and vent to when a client drops you suddenly.
Nadira Bostic, another freelance writer, adds practical advice: "Join Facebook groups, Slack groups, talk more on LinkedIn. It might not lead to you getting work immediately, but you'll learn new things from people who've been doing this longer than you have. Plus, you might be able to share tips with people and help them, and maybe they'll help you in return."
Pro tip: Don't just join communities — engage regularly. I set aside 30 minutes each morning to check in with my freelance groups and LinkedIn feed. It's led to collaborations, referrals, and friendships that make this freelancing journey feel a lot less solo.
Do: Treat Freelancing as a Real Job
This might be my favorite piece of advice from Imogen: "Do set clear boundaries from the start. Decide your working hours and when you'll communicate with clients, and stick to those rules. This will protect your time and your well-being. Do treat your freelancing like a 'proper' job. Have a start and end time. Take regular breaks. And have money set aside for holidays, sick time and personal days."
I used to work a bit chaotically and constantly. These days, I have set working hours (8pm to 12 am, with flexibility for calls during the day), a dedicated workspace (not my bed anymore!), and actual weekends. I batch my client communications into specific time blocks, and set aside dedicated time for non-billable admin work. The result? Better work, happier clients, and a much healthier relationship with my business.
The Don't's: Learn From Our Mistakes
Don't: Undercharge Just Because You're New
In my first few months, I charged $500 per blog post for SEO content writing because I felt guilty asking for more as a newbie. The reality? That rate barely covered my time, let alone taxes and business expenses. It took me six months to work up the courage to raise my rates — and you know what? Not a single client dropped me when I did.
Hsing Tseng
“Don't undersell yourself. Know your worth and charge accordingly. Research rates and ask for what you deserve,” says Imogen.
Don’t: Ignore the Business Side
Freelancing isn’t just about doing great work; it’s also about running a business. That means:
- Invoicing: Make it easy for clients to pay you on time.
- Contracts: Protect yourself with written agreements. A verbal agreement won’t cut it.
- Taxes: Set aside money for taxes from every payment you receive.
Tools That Saved My Sanity:
- Accounting: Wave or QuickBooks
- Contracts and E-Signatures: Google Docs + PandaDoc
- Project Management: Airtable
Still, a hefty tool stack isn’t necessarily the answer to all your problems. You don’t need “all the tools” to be successful. What works for me might not work for you, etc.
Hsing Tseng
Don’t: Panic During Slow Months
Remember what I said about feast or famine? That happens to every freelancer. Instead of spiraling, use slow months to:
- Market Yourself: Update your portfolio, revamp your website, or work on LinkedIn posts.
- Upskill: Take a course or dive into a book that helps you level up.
- Rest: Freelancing is a marathon, not a sprint. Take advantage of the downtime to recharge.
Don’t: Burn Out By Saying “Yes” To Everything
Early on, I said yes to everything — social media management, email marketing, website copy, etc. I was spreading myself thin and doing a mediocre job at all of it. Once I niched down to focus on B2B long-form content writing, not only did the quality of my work improve, but I started attracting better-fitting clients who valued my expertise.
“Don't be afraid to say no. Not every project or client is a good fit. It's better to turn down work that isn't right for you,” says Imogen.
Don’t: Work for Free
"But it'll be great exposure!" If I had a dollar for every time I heard this, I wouldn't need to freelance anymore. Here's the thing about exposure: it doesn't pay the bills. While there might be strategic reasons to take on pro bono work (like building a portfolio in a new niche or supporting a cause you believe in), don't make a habit of working for free.
I learned this lesson after spending two weeks on a "trial project" that was supposed to lead to ongoing work. Spoiler alert: clients who don't value your time during the trial rarely value it after. These days, I'm happy to provide samples of relevant past work, but my time and expertise come with a price tag.
Don’t: Jump Into Freelancing With Rose-Colored Glasses
“Don’t jump into freelancing only because of the flexibility + potential of no income ceiling + (insert any other benefit that seems glorified when not seen along with the scary parts of freelancing),” says Akansha Rukhaiyar. “The grass will seem greener on the other side (self employment) if you don’t know the entire story.”
She’s right. I've seen too many people dive into freelancing because they hate their boss or want to work in their pajamas. While flexibility is great (and yes, I'm writing this in sweatpants), it shouldn't be your only motivation.
The reality check? That flexibility comes with irregular income, self-imposed discipline, and the constant hustle of running your own business. Make sure you're running toward freelancing for the right reasons, not just running away from a bad job. (Speaking from experience…)
Don’t: Hesitate to Ask for Help
My biggest regret from my first year? All the hours I spent struggling with problems that more experienced freelancers could have solved in minutes. As Akansha Rukhaiyar reminds us, "No question is dumb, no doubt is too small."
When I finally worked up the courage to ask former colleague Anna Burgess Yang how she handled scope creep, she shared a contract template with me that has saved me countless hours and headaches. That’s just one example of how other freelancers have saved my butt.
Hsing Tseng
Whether it's pricing strategies, client red flags, or the best project management tools — someone in your network has probably already figured it out.
Navigating the Emotional Rollercoaster
As a freelancer, some days you'll feel like you're crushing it, and others you'll wonder if you made a huge mistake. Both feelings are normal, and neither lasts forever.
Here's what helps me stay sane:
- Having a routine (even though you technically don't have to)
- Setting OKRs for yourself
- Finding other freelancer friends who get it
- Celebrating small wins (landed a new client? That's cake-worthy!)
- Keeping track of positive feedback for those inevitable imposter syndrome days
What I Wish Someone Had Told Me
Here’s the truth: there's no "right" way to start freelancing. Whether you're planning a careful transition or considering your own YOLO moment, the key is to just start somewhere. My chaotic dive into the freelance world worked out, but not because I did everything right — but because I stayed flexible, learned from my mistakes, and kept showing up even when things got tough.
The best freelancers aren’t just lucky or more skilled; they’re resilient. Everyone’s been knocked down a few times, but the successful freelancers just keep getting back up. Remember: everyone started from square one at some point and kept going and going, one project at a time, until they figured it out. You've got this.
Ready to take the leap? Start with one small step today. Update your LinkedIn profile. Reach out to one person in your network. Draft your rates. The path to freelancing doesn't have to be all or nothing — unless, of course, you're feeling particularly YOLO about it. In that case, I'll be here cheering you on, sharing war stories, and reminding you that yes, this is bonkers, and yes, you're going to be okay.
