Challenges of Building a Successful Freelance Career

The Freelancer’s Paradox: “If I can earn more than RM10,000 on my own and work whenever I want, why should I tie myself to a company?” — A Malaysian freelancer. Let’s call them FL. At first, freelancing felt like freedom. No boss. No office politics. No fixed schedule. No ceiling on their income. But years later, FL realised they had not escaped the system—they had simply become the entire system. When they stopped working, the whole business stopped earning. In their later age: 1. They had little retirement savings (no employer contributing min 13% to their EPF) 2. Property financing became difficult because of inconsistent income. 3. During good times, they burned out. 4. During quieter months, they struggled financially. 5. They could not afford to be sick. 6. Public holidays became “days without income.” 7. The freedom to work anytime became working all the time. 8. Higher personal tax. 9. Competing with larger companies offering broader services & stronger resources. 10. Competing with freelancers who charge much less. 11. Continuously fund their own training to remain relevant. The problem was not freelancing. The problem was building a career that depended entirely on one person’s time, energy & health with no capped downside. If freelancing is the life you choose: 1. Contribute consistently to EPF or long-term investments. 2. Set an annual budget for professional development. 3. Live below your average income, ideally less than 50%. 4. Build recurring revenue through retainers or long-term contracts. 5. Dedicate regular time to branding, marketing and lead generation. 6. Maintain an emergency fund (6–12 months of expenses) 7. Productise, automate or delegate parts of your work. 8. Protect yourself with medical and income-protection coverage. Another possible path is to move from working alone towards building a business supported by an established system. For some, this means developing their own team, processes and IP. For others, it may mean joining a franchise, where the brand, programmes, operational systems and support network already exist. This thinking also shaped the MicFront franchise model. It was designed for people who believe in education, children’s development and the power of communication, but may not want to create every curriculum, resource and process from the ground up. Of course, a franchise is not effortless, nor does it guarantee success. It still requires capital, leadership, discipline and consistent execution. The difference is that you are building upon a tested foundation instead of beginning entirely alone. Freelancing provides independence. A well-built business creates leverage. A franchise offers a more structured starting point. The right path depends on the kind of life, responsibility & future you want to build. True freedom is not simply being able to work whenever you want. It is having the systems, resources & support to keep creating value without everything depending entirely on you.

If you’re a full-time freelancer (esp. <5 yrs exp.), don’t make these 9 mistakes: 1) Changing your positioning too frequently (“SaaS writer” one month, “finance writer” the next.) You dilute your expertise in front of ICPs who’re looking at you from afar 2) Publicly marrying a niche (unless you know exactly what you’re doing). It shrinks your surface area for opportunities 3) Overlooking how your portfolio “looks.” (A good presentation creates good perception.) 4) Building a portfolio that shows just samples. (Serious prospects want to see what you shipped, why you chose that approach, what moved because of it... Screenshots + context beat 12 Google Doc links.) 5) Discounting too quickly in negotiations. (The moment there is pushback, you lower the number instead of tightening scope, changing terms, or clarifying the outcome.) 6) Never documenting wins properly. (You finish a project and move on, and you forget to capture testimonials, metrics, screenshots, and process notes while everything is still fresh.) 7) Not tracking your effective hourly rate. A $2,000 project sounds great until you realize it took 40 hours, five calls, and three rounds of revisions. 8) Not building a simple pipeline.. no weekly outreach target, no follow-ups, no referral asks, no clear “who do I want to work with” list. So work becomes luck + mood. 9) Letting one client become your entire business. (One big retainer feels safe until it becomes a single point of failure, and then you’re negotiating from panic instead of leverage.) What else?

The first 6 months of my freelancing journey: I earned €500 a month. I struggled to find clients. I questioned my skills. And honestly, I felt like giving up more times than I’d like to admit. What changed everything: I stopped chasing clients and started building a trusted freelancing brand. The kind that draws clients to you. Here’s how you can do it too: 1. Your content is your portfolio. ✔️ Share lessons you’ve learned. ✔️ processes you follow, and small wins. ✔️ Teach something valuable instead of just selling. 2. Build and refine your skills ✔️ Clients pay for expertise ✔️ Every project is a chance to level up. ✔️ Focus on improving both technical and soft skills. 3. Master negotiation ✔️ Understand what the client truly needs. ✔️ Don’t undersell yourself to "close the deal." ✔️ Be clear on what is that you bring to the table. ✔️ Confidence grows when you’re ready to say no. 4. Network with intention ✔️ Engage with potential clients daily. ✔️ Build relationships with fellow freelancers. ✔️ Nurture connections—they lead to referrals. The goal isn’t to be just another freelancer. Be the freelancer clients trust and refer. PS: Need more tips? Grab my freelancing cheatsheet (500+ freelancers already have it) here: https://bit.ly/3LWwyZ7

I still remember the day I left my prestigious marketing lecturer job in my 30s to dive into the world of freelancing. It felt like stepping off a cliff into the unknown. The first shock? Realizing I was competing with freelancers half my age. Doubt crept in. "Have I made a terrible mistake?" I wondered, feeling out of place and outpaced. But here's what I discovered: 1. Time is a great filter. Many young freelancers left the field, tried something else, stopped etc. but I persevered. 2. Age isn't a creativity killer - it's an asset. My maturity became my secret weapon. 3. Trust is everything. Clients valued my experience and reliability. Fast forward to today: I'm 41 now I'm not just freelancing I'm building an agency and multiple ventures! The key? Continuous effort and understanding the freelance game: * It's not just about skills - it's about handling pressure and building connections. * Clients want peace of mind and deliverables they can trust. * The ability to manage projects and people is invaluable. For those feeling stuck or doubting themselves, PS: If you take action, nothing can stop you. Here's how to start: 1. Plan your goals: Where are you now? Where do you want to be in 2 months? 2 years? 2. Set SMART Goals: Specific, Measurable, Achievable, Relevant, Time-bound. 3. Create a roadmap: Use mind-mapping and tools like Notion to visualize your path. 4. Hold yourself accountable: You're in charge of your journey. 5. Regular self-growth checks: Measure your progress or find an accountability partner. See, age takes a backseat when quality work shows up. Your unique experiences are your superpower - use them! #CareerTransition #FreelanceSuccess #PerseveranceWins #NeverTooLate

Freelancing is hard. Anyone who tells you otherwise is ignorant, lying, or trying to sell you something. For 15+ years my freelance business has been a parade of problems. That’s not to say I plan to stop, or that I recommend another path to freedom-hungry creatives and consultants, but that each of us must ask the Six-Figure Question… “Which problem do I prefer?” Take specialization, for example. I coach advanced freelancers one on one and in groups. Many are still generalists. They enjoy solving a variety of creative and intellectual problems. Variety is the spice, after all. The fear of missing out speaks up: “What if I niche down and someone outside of my niche doesn’t want to hire me?” There’s also a fear of boredom: “I’m just not sure I want to do the same project over and over.” What I bring up, gently, is that boredom may actually be preferable to the problems that motivated them to get in touch with me. I also point out that our conversation was never about specialization being a perfect solution. No perfect solution exists. My role as a coach involves helping my clients make decisions based on logic, hope, and what I’ll call the persistence of a problem-full reality. Any big move you make in a freelance business involves picking the path with the set of problems you prefer. Problems with being a generalist: - Not the go-to person for solving a painful, expensive problem. - Difficulty standardizing processes for so many different tasks and projects. - Complicated marketing because anyone with a budget and pulse can be a client. - Harder to charge a premium because you’re the jill-of-all-trades, not the specialist. - Harder to protect and raise your effective hourly rate because your processes aren’t dialed in. Problems with being a specialist: - Multipassionate types, myself included, struggle to stay interested after we’ve solved the core problem. - You can’t depend on referrals because the people you know don’t know enough of your dream clients. - Therefore, you must develop a Morning Marketing Habit and generate leads who are strangers. - Therefore, you must charge premium prices to subsidize hours spent on marketing and sales. - Therefore, you must work on the confidence required to charge premium prices. Staying a generalist is playing the freelance game on hard mode. Being a specialist is no walk in the park either. Yes, freelancing is hard, but some problems, such as the feast-or-famine roller coaster, have a higher emotional toll than other ones (”I’m not stimulated by what my high-paying clients are asking me to do.”) This whole endeavor isn’t about building a problem-free life or business but purposefully picking problems and tradeoffs you can live with. I’d rather have a repetitive, profitable business and put myself in a position to hire support and get my entertainment elsewhere. Pick your problems with the same care you pick your friends. Does this change your mind about any moves you need to make?

I left my full-time job 7 years ago this month (time flies!) to start freelance writing. Here are 7 things I've learnt that I wish I'd have known back then: 1/ Create a separate bank account for all of your income and pay yourself a salary from that account. It stops you living invoice-to-invoice and helps you manage cashflow. It's also good for saving $$$ if you only take X amount each month. Anything you earn on top is saved. 2/ Tax is expensive. Create another bank account (or space inside your existing one) to save for it. Put 30% of every invoice in there. Have an emergency back-up, too... Especially in your first year. Payments on account in the UK are a nightmare. 3/ Relationships are EVERYTHING. I wouldn't have 99% of my clients, nor work with companies with such high budgets, without an intro to them (or vice versa.) 4/ Set aside at least 1 hour/week to learn new stuff. Never think you've learnt it all. 5/ Do what you said you'd do, when you said you'd do it. 6/ If your rates don't scare you, they're not high enough. Think of the value you bring with your content and charge an extra 20% for the benefits you don't get for being a freelancer (i.e. insurance, PTO, sick leave, etc.) 7/ Work-life balance is HARD when you do both in the same house. Have a dedicated workspace and office hours. Don't work outside of those. Nothing is ever that urgent. I can't stick to 7 so here's a bonus: Don't feel pressured to set long working hours. Just because you worked 8 hours/day in an office, it doesn't mean you have to now. You'd probably drag out the same work you could do in 4 hours by cutting distractions and focusing. (Now, I only do "real work" in the afternoon.) What would you add? 👇

Six years ago, I took the leap and went freelance (right before a pandemic! 😅). Here are six things I've learned since then: 1. Being self-employed is HARD. Your entire career trajectory, success, income, happiness, etc., is all based on you. That's not for the faint of heart, especially when you're faced with imposter syndrome, feast or famine seasons, setting boundaries, marketing yourself, and generally having the motivation to keep going when someone isn't telling you what to do. 2. But being self-employed is REALLY exciting and can be super rewarding. Again, your entire career trajectory, success, income, happiness, etc., is all based on you — and that's great! I have been able to lean into my strengths and double down on the work that I really enjoy doing (which no boss or reorg can then move me off of). If I want to pivot into an industry or change an offering, I can just do it. And I enjoy the flexibility and autonomy in my schedule the most. 3. My biggest Achilles heel has been confidence. I'm sure I'm not alone when I say that having the confidence to offer something of value to others or think I know what I'm doing has been the biggest hindrance to me. "Who am I to think that I could run my own business based solely on my skills and talents?" "Sure, I've been writing content for 20+ years, but do I really KNOW anything or have anything to offer?" It's kind of a constant fight. 4. I had to learn how to market myself in terms of value offered. This is something I'm still working on, but I've come a long way from the first days of pitching just my experience and what I could do. Then I learned how to position a pitch to address "you" and a client's needs. Today, I'm working on positioning myself in terms of the results I can achieve. It's an ongoing journey. 5. Pricing is hard (see # 3: Confidence above). Before I went freelance, I crash-coursed myself in anything I could get my hands on about how to do freelance right, so I went in knowing about premium pricing. Still, it took me a while to move out of hourly-based pricing to project-based, and now trying to understand value-based pricing (see # 4 above). I've also learned that while raising my rates freaks me out, it often doesn't freak my clients out! 6. I've been doing freelance "wrong" for six years, but I'm not giving up yet. I've always relied on, "Well, at the end of the day, I'm a great writer, and my work will speak for itself, and clients will flock to me!" Big fat NOPE. While I've had the chance to work on some really amazing projects with cool clients, freelance hasn't turned into what I expected it to be. And it's because I haven't run it like a business. So at the six-year mark now, I'm doubling down on learning how to actually run this thing like a business: systems, networking, positioning as a strategy partner, all the things. I could probably easily crank out six more learnings from my freelance years, but that's what I've got for you today!

Advice I would give to you BEFORE you start your freelance business if we were sitting down having coffee: - Don't low-ball your pricing. It might be tempting to price your services super low, but it actually makes you seem less desirable. Clients will think, "If the price is this low is the service even good?" You can price a little lower in the beginning to get experience and client reviews, but make it clear it's a limited-time starting price. - Don't stay hourly. Hourly means you're paid based on the time you spend doing the work, but as you become more efficient, you're paid less while still providing the same (if not better) value. Focus on getting paid for the value you provide, not the amount of time it takes. Move to project-based or retainer as soon as you can. - Niche down. You can start as more of a generalist in your field, but don't stay there. Determine what you want to be known for and lean in to that by niching down. You'll also be able to charge more because your credibility is specific. Think about the knowledge, experience, and expertise you have and how that can help you to niche down. - Create work boundaries. It's easy to work all the time when your income is directly tied to your output. You'll eventually get burned out if you don't have clear boundaries in place. Determine when you're working and when you're not, then put your laptop away. - Don't take just anyone as a client. Make sure clients are a good fit for working with you. You'll regret it if you take on a crappy client just for the money. Explain the benefits of your services but don't sell your soul just to get a client. Your dream client could be right around the corner. - Create community in your work. Being a freelancer can be lonely. Your family/friends may not get what you do or how to help when something comes up. Find a work community that you can lean on when you have questions, need advice, need resources, and for general connection. - Always be learning. Keep up with changes in your field and spend time learning new skills if it makes sense for your services - the higher skilled you are the more you can charge for your expertise. - Keep your business and personal finances separate. Don't make it messy by combining your freelance businesses finances and personal. I recommend following Profit First (a book by Mike Michalowicz). Dedicate a monthly CFO day. The percentages I use: 5% goes to profit acct 50% goes to owner pay acct 15% goes to tax acct 30% keep in operating expense acct - Be aware of scams and be thoughtful where you search for jobs. There are so many scam job postings out here. If it seems too good to be true, it likely is. There are also a lot of freelance job boards/platforms that don't post quality jobs and recirculate low-paying jobs. Find your trusted sources and revisit them frequently + sign up for notifications of new jobs. Continued in comments ⬇️

When I left my corporate job and set out on my own, I thought I was prepared. I had a year of savings, a growing side hustle, and a plan. But no one tells you what reinvention really demands of you. Here are the 3 biggest challenges I faced when building a portfolio career: 🌀 1. Income Whiplash: Some months felt like I had cracked the code. Others? I was quietly panicking and tapping into savings. Eventually, I realized I needed a baseline - something that provided consistency and aligned with my values. Coaching and facilitation topped my skill stack, so I leaned into them and secured a fractional role with a leadership development firm I love. 💬 2. Isolation: I never expected to miss Zoom meetings, hallway chats, or offhand brainstorms. But working solo got lonely - especially during the pandemic. What changed everything? Reaching out to people I admired and forming creative partnerships. The result: more connection, more opportunity, and a lot more fun. ⚠️ 3. I Re-created the Grind I Was Trying to Escape: At first, I thought I had found freedom. But I had unknowingly created another job for myself. My calendar was full. And my flexibility? Better ...but my earnings were still tied to me showing up several hours every day. That’s when I committed to 5-hour workdays. This constraint has forced me to rethink my business model around leverage, value, and joy - not just constant hustle. Reinventing your work life isn’t for the faint of heart. But it can lead to something far more meaningful than you might be able to imagine. 👉 I’d love to know: What’s been the biggest challenge (or fear) in your own work/life reinvention? Let’s compare notes 👇 #Reinvention #PortfolioCareer #Solopreneurship #FutureOfWork #TheNewWealth #CareerTransition

Picture this: It’s 2022, I’m burnt out at my agency job, and something inside me snaps. Two weeks later, I quit. Two months after that, I abandon the job hunt and dive headfirst into freelancing… with zero clients lined up. Was it reckless? Absolutely. Did it work out? Eventually — but not before I learned some hard lessons. Freelancing is equal parts terrifying and liberating. While I don’t necessarily recommend my “leap first, figure it out later” approach, I can share what I learned the hard way — so you don’t have to. I also asked some friends in Top of the Funnel for their tips, and together, here's a mega-list of do's and don'ts for starting freelancing! ✅ The Do’s: What Actually Works ✔️ Build Your Emergency Fund First – Have at least 3-6 months of expenses saved. ✔️ Start With Your Network – Your next client could be a former coworker, manager, or even a friend. ✔️ Build a Pipeline Early – Even when you're busy, keep pitching and networking so you’re not scrambling later. ✔️ Charge What You’re Worth – Low rates = recipe for burnout. Research market rates and price accordingly. ✔️ Find a Great Tax Pro – Self-employment taxes will sneak up on you. Don’t wait to figure them out. ✔️ Learn to Be Tenacious – It’s not just about talent. Freelancers who stick around the longest tend to win. ✔️ Work On Your Portfolio – Showcasing great work makes a big difference. ✔️ Request Testimonials – Happy clients are your best marketing tool. ✔️ Find Community – Fellow freelancers can be your biggest source of referrals, advice, and sanity. ✔️ Treat Freelancing Like a ‘Real Job’ – Set work hours, take breaks, and budget for sick time & vacations. ❌ The Don’ts: Learn From Our Mistakes 🚫 Don’t Undercharge Just Because You're New – Clients won’t magically start paying more later. 🚫 Don’t Ignore the Business Side – Contracts, invoicing, and financial planning are just as important as the work itself. 🚫 Don’t Panic During Slow Months – Use downtime to market yourself, build skills, and rest. 🚫 Don’t Burn Out on Freelancing Platforms – Fiverr & Upwork can be a starting point, but they’ll underpay and take a cut. Keep your revenue streams diverse. 🚫 Don’t Say Yes to Everything – Bad-fit clients and projects will drain you. Be selective. 🚫 Don’t Work for Free – “Exposure” doesn’t pay the bills. Even trial projects should be paid. 🚫 Don’t Jump Into Freelancing With Rose-Colored Glasses – Flexibility is great, but freelancing also means irregular income, constant outreach, and self-discipline. 🚫 Don’t Hesitate to Ask for Help – Whether it's pricing, contracts, or taxes, someone in your network has already figured it out — lean on them. 👉 Want the full breakdown, plus real stories from experienced freelancers? I dive into each of these lessons (and how I learned them the hard way) in my latest post for command + create, linked below. Thinking about making the leap? Already in the trenches? Drop a comment — let’s talk about it. 👇