Career Roadmap Creation

In my 15-year career in tech + freelancing, here are some truths: 1) You are just a resource, replaceable anytime, always be prepared with options! Especially for freelancing, never settle for a single project, always keep 1+n and never depend on one income stream — diversify (consulting, teaching, side projects). 2) Office/Company/Clients/Colleagues!= Family (don't confuse, they don't) 3) Learn to say “No” — overcommitting kills both productivity and peace of mind. 4) Upskilling is your insurance. The tech you know today can be irrelevant tomorrow. 5) Don’t chase titles; chase impact and freedom — those last longer. 6) Networking beats résumés. Opportunities come from people, not portals. 7) Emotional intelligence > Technical brilliance when it comes to leadership. 8) Work-life balance isn’t a luxury; it’s what keeps you in the game long-term. 9) Document everything — it protects you, helps others, and earns respect. 10) The real growth happens when you start mentoring others. I learned the painful way; you don't have to!

5 Priceless Freelancing Growth Tips I Wish I Knew Earlier ➊ The most underrated freelancing skill is reliability. Deliver on time, keep your word, and communicate well. Clients value freelancers they can depend on more than those with the flashiest portfolios. Reliability builds trust—and trust leads to repeat business. ➋ Charge for the value you create, not the hours you spend. Early on, I undervalued my work and billed only for time. The truth is, clients care about results, not how long it takes you to deliver them. Price your services based on the impact you bring to their business. ➌ Your network is your safety net. The best freelance gigs rarely come from job boards. They come from referrals, conversations, and relationships. Make networking a regular part of your workflow—it’s just as important as your deliverables. ➍ Treat every client like your most important one. Even small projects can lead to big opportunities. Go above and beyond for every client—they’ll remember, refer, and come back for more. ➎ Invest in skills that clients pay top dollar for. Identify high-value services in your industry and master them. Whether it’s a technical skill, communication, or strategy, clients will gladly pay a premium for expertise that solves big problems. Freelancing isn’t just about finding clients—it’s about building a sustainable, thriving business. What’s the best freelancing advice you’ve ever received?

How do you build a career out of freelancing and actually make it sustainable? Here’s what’s helped me stay engaged, avoid burnout, and make freelancing a stable, financially rewarding path. 1. Diversify your income. Never rely on one client, one industry, or one type of work for your entire income. Spread the risk. When one sector slows down, others keep you steady. This effort has kept my business thriving through economic shifts and client churn over the last twelve years. 2. Pivot when the market shifts. Freelancing is about adaptability. You’ll need to evolve as client preferences change, technology advances, and industry trends shift. Making small and big pivots as a freelancer (in any career) is necessary for long-term viability. 3. Invest in continuous learning. Your expertise skills are your business, so you have to make the time to sharpen them. Take courses, learn complementary disciplines, and explore tools that extend your value. The freelancers who learn fast stay relevant. 4. Protect your enjoyment. Not every project has to be lucrative. Some should simply be interesting. Creative satisfaction fuels consistency. Without joy, freelancing becomes just like a salaried full-time role and burnout will find you fast if all your work is mundane. 5. Design for flexibility, not just $$$. Money matters, but so does how you earn it. Freelancing ideally gives you the freedom to shape your schedule, your clients, and your priorities. Continue to design your practice around your own fulfillment, not just income. Freelancing can be a stable, fulfilling career if you treat it like one. It's an active practice and not the type of job you can leave on autopilot. I wrote more on these tactics for building a lasting career as a freelancer in the latest edition of the Career Freelancer newsletter this week, check it out below. #freelance #selfemployed #solopreneur #freelancetips

In the last month, I’ve had 8 offers of freelance writing work. I turned them all down because I’m booked until 2026. This isn’t a boast. It’s a broadcast: work is out there. These are the 8 strategies I used to get oversubscribed: 𝟭. 𝗪𝗲𝗯 𝗰𝗼𝗽𝘆 𝗽𝗿𝗼𝗷𝗲𝗰𝘁 – 𝘃𝗶𝗮 𝗲𝗺𝗮𝗶𝗹 This relationship started in 2021 when I wrote a cold email to the founders that was part poem, part fanmail, part brain fart. 💌 𝗦𝘁𝗿𝗮𝘁𝗲𝗴𝘆: Send client-centric, quirky, human cold pitches consistently. That’s how I built my entire business with no contacts, no experience, and no portfolio. 𝟮. 𝗖𝗼𝗻𝘁𝗲𝗻𝘁 𝘄𝗿𝗶𝘁𝗶𝗻𝗴 – 𝗿𝗲𝗳𝗲𝗿𝗿𝗮𝗹 𝗳𝗿𝗼𝗺 𝗮𝗻𝗼𝘁𝗵𝗲𝗿 𝘄𝗿𝗶𝘁𝗲𝗿 When I started working with one of my clients, I added their other writer on LinkedIn to say hi. Months later, he came to me with work he couldn't take. 👯 𝗦𝘁𝗿𝗮𝘁𝗲𝗴𝘆: Network with other writers in your niche so you’re an easy choice when they're booked. 𝟯. 𝗖𝗼𝗻𝘁𝗲𝗻𝘁 𝘀𝘁𝗿𝗮𝘁𝗲𝗴𝘆 – 𝗶𝗻𝗯𝗼𝘂𝗻𝗱 𝘃𝗶𝗮 𝗳𝗼𝗿𝗺 No prior relationship with this brand. Dream client. They found me a week after I added 10+ links to my contact form. ☎️ 𝗦𝘁𝗿𝗮𝘁𝗲𝗴𝘆: Make it INSANELY EASY to contact you and be clear who you’re a fit for. You need to put off the wrong people to attract the right ones. 𝟰. 𝗕𝗿𝗮𝗻𝗱 𝘃𝗼𝗶𝗰𝗲 𝗽𝗿𝗼𝗷𝗲𝗰𝘁 – 𝗶𝗻𝗯𝗼𝘂𝗻𝗱 𝘃𝗶𝗮 𝗲𝗺𝗮𝗶𝗹 An agency reached out cold after finding me on LinkedIn. 🔍 𝗦𝘁𝗿𝗮𝘁𝗲𝗴𝘆: Make sure your bio, About, and work experience sections say what you do and who for. People use LinkedIn as a search engine. 𝟱. 𝗩𝗶𝗱𝗲𝗼 𝘀𝗰𝗿𝗶𝗽𝘁 – 𝗟𝗶𝗻𝗸𝗲𝗱𝗜𝗻 𝗺𝗲𝘀𝘀𝗮𝗴𝗲 I had a intro call with this agency owner in Jan. She didn't have any work then, but we stayed in touch. 💡𝗦𝘁𝗿𝗮𝘁𝗲𝗴𝘆: Suggest a pre-emptive intro even if there's no offer. You'll be more memorable if you've connected face-to-face. 𝟲. 𝗧𝗩 𝗽𝗿𝗼𝗱𝘂𝗰𝗲𝗿 𝗷𝗼𝗯 – 𝗪𝗵𝗮𝘁𝘀𝗔𝗽𝗽 𝗳𝗿𝗼𝗺 𝗳𝗿𝗲𝗲𝗹𝗮𝗻𝗰𝗲𝗿 𝗜’𝗱 𝘄𝗼𝗿𝗸𝗲𝗱 𝘄𝗶𝘁𝗵 Ok so strictly I don't work in this role any more but this is still relevant... 🗣️ 𝗦𝘁𝗿𝗮𝘁𝗲𝗴𝘆: Stay. in. touch. with. everyone. you’ve. ever. worked. with. 𝟳. 𝗪𝗲𝗯 𝗰𝗼𝗽𝘆 𝗽𝗿𝗼𝗷𝗲𝗰𝘁 – 𝗳𝗿𝗼𝗺 𝗮 𝗕𝟮𝗕 𝘀𝗼𝗰𝗶𝗮𝗹 𝗺𝗲𝗱𝗶𝗮 𝘀𝗽𝗲𝗰𝗶𝗮𝗹𝗶𝘀𝘁 𝗦𝘁𝗿𝗮𝘁𝗲𝗴𝘆: Network with people in your niche 𝘣𝘶𝘵 𝘰𝘶𝘵𝘴𝘪𝘥𝘦 𝘺𝘰𝘶𝘳 𝘥𝘪𝘴𝘤𝘪𝘱𝘭𝘪𝘯𝘦 so that you can team up without competing. 𝟴. 𝟮𝘅 𝗴𝗵𝗼𝘀𝘁𝘄𝗿𝗶𝘁𝗶𝗻𝗴 𝗽𝗿𝗼𝗷𝗲𝗰𝘁𝘀 - 𝗳𝗿𝗼𝗺 𝗲𝘅𝗶𝘀𝘁𝗶𝗻𝗴 𝗰𝗹𝗶𝗲𝗻𝘁 💎 𝗦𝘁𝗿𝗮𝘁𝗲𝗴𝘆: Make yourself indis-freaking-pensable to your current clients. You have a ~70% chance of getting rebooked VS ~5% of selling to a brand new prospect. These aren’t quick fixes. It took me ~12 months to go from feast-and-famine to having a healthy pipeline of recurring revenue. But find a mix that works for you, commit to it over the long term, and you will get booked. And if you're a writer/freelancer in B2B please say hi - I'd love to send work your way ⚡ 

Don’t quit your job until you’re making $1,000/month as a freelancer. Here’s why: Freelancing is freedom, but only when you’re not constantly chasing the next paycheck. - You know how to find work. - You’re reliable. - And clients trust you enough to pay. Here’s how you can build a $1,000/month freelancing system: 1/ Start building while you’re still employed. Don’t wait to quit to figure things out. Use your evenings and weekends to test the waters, find clients, and refine your offers. 2/ Treat freelancing like a business. Set up systems—track leads, follow-ups, and finances. Even a simple spreadsheet can help you stay organized. 3/ Create one core service and master it. The biggest mistake? Offering everything. Pick one service you can deliver exceptionally well and make it your signature offering. 4/ Focus on landing your first three clients. Forget scaling for now. The first three clients teach you everything—how to sell, deliver, and build trust. 5/ Build proof of work. Nobody cares about titles; they care about results. Case studies and testimonials speak louder than words. 6/ Learn to price strategically. Start with introductory rates, but don’t undersell yourself. As you build credibility, adjust your rates accordingly. 7/ Invest in learning sales and communication. Freelancing is 50% skills, 50% sales. The better you are at pitching your value, the faster you’ll grow. Hope this helps!

When you've been freelancing a while, you realise that more hustle doesn’t equal more clients. The problem usually isn’t that you’re not pitching enough… it’s more that not enough of the right people know you exist or trust your judgement. Getting people to SEE you is one thing, but getting the like and trust factor is a different beast entirely. Here’s how I do it. 1. Build a warm lead ecosystem instead of using one-off tactics Most freelancers treat lead generation like a buffet: a bit of posting here, a few DMs there, maybe a networking call if they feel brave. Individually, these actions can work. But it’s when they’re all used together, consistently, that they turn into a flywheel that pretty much runs on its own. Think of your lead generation as an ecosystem with different layers of visibility, proof, and connection. 2. Create a “people map” It’s tempting to go with the scattergun approach of finding leads, and sometimes this can work (especially early on when you’re not 100% sure who you serve). But, if you want to really drill down into it, ask yourself: Where are the rooms full of clients who already want what I do? Use the answer to start building a living document of the people, companies, and communities worth staying visible in. - Founders you admire - Ideal client companies - Newsletter writers your audience reads - LinkedIn creators talking to your people - Agency owners who subcontract - Podcast hosts in your niche 3. Warm yourself up in rooms before you reach out A CLASSIC freelancer mistake: 1. Arrive. 2. Pitch (and hope that it turns into something). A better approach: 1. Observe 2. Add value 3. Become familiar 4. Pitch only if it makes sense I call this “warming up” and it creates warmer leads that are more open to you pitching/asking for work when the time is right. Some low-effort, high-impact warm-ups include: - Thoughtfully commenting on content - Replying to newsletters or stories - Sharing content with an added insight - Offering a micro-observation about their brand or positioning Once you start building out your people map, you can spend 5-10 minutes a day warming a few people on it. 4. Show your brain Clients don’t hire you because you write, design, code, or strategise. They will often hire you because of how you think and how you show up. Share: - How you make decisions - What questions you ask in projects - Problems you’ve solved and how - Mistakes you’ve made + how you fixed them - Screenshots from inside your process - 60-second voice notes or short videos explaining an insight Aim for one “thinking” post per week, which could be a small breakdown of how you’d approach a client problem. 5. Use micro-asks to unlock hidden opportunities Instead of “Do you need help?”, ask smaller, softer questions that open the door. Try: - “How are you currently approaching X?” - “Do you ever outsource Y?” - “Who owns X inside your team?” Send 5 micro-asks per week to people already in your orbit.

I’ve been making six-figures freelancing for many years now. But if I woke up tomorrow with zero clients and had to get back to $100k by summer… here are the first three moves I’d make. MOVE 1: I’d design the offer around the buying decision, not my skillset This is where most freelancers go wrong. They start with their service. I wouldn’t. I’d reverse-engineer: • how the client gets internal approval • what makes the decision feel “safe” • what risk they’re actually trying to avoid Then I’d build the offer to remove friction from that moment. That’s why I’m able to close fast without “selling.” It’s not because I’m persuasive, it’s because I’m aligned with how decisions are actually made and I’ve match made any offer to their specific pain. MOVE 2: I’d treat my business like a customer journey, not a to-do list Most freelancers wake up asking: “What should I work on today?” I’d ask something very different: “What pieces am I moving down the board today?” Every single day, I’d do at least one thing for each transformation of the customer journey we use to organize our business: • Stranger → Lead • Lead → Client • Client → Lifetime Client That might mean: publishing one piece of visibility following up with warm leads developing a valuable recurring offer for current and past clients Most freelancers stay busy. $100k freelancers stay intentional. MOVE 3: I’d stop measuring effort entirely, and only track constraint Most freelancers measure: • hours worked • posts published • messages sent None of that predicts income. I’d track just one thing: “Where does progress slow down?” Then I’d redesign the business to relieve that constraint. If sales stall → the offer isn’t safe enough. If leads stall → the problem isn’t visible enough. If revenue stalls → value isn’t being captured cleanly. Income doesn’t grow evenly. It grows at the constraint. That’s why some freelancers work less and earn more... they’re relentless about neutralizing choke points. Most freelancers optimize for activity, the appearance of progress… I’d optimize for decision flow, directional effort, and constraint removal. None of this is complicated, but it takes years to piece together on your own if you don’t know what to look for. So on 12/30, I’m hosting a live, practical workshop where we’ll map these three levers directly onto your business and turn them into a clear, week-by-week plan. Everyone leaves with a personalized handbook, and live attendees will also get access to a tool I’ve been building to make pricing decisions far simpler. We’re keeping the room small, and the last 2 workshops sold out. If you want to start 2026 on the exact path to a $100k year, comment “26” and I’ll send you the link.

I started my freelancing journey when my daughter was an infant… and she recently got her driver’s license 🤯 In honor of my daughter, here are 16 things I’ve learned since I started my journey: 1) Find your people. Working solo can feel overwhelming and lonely at times so find others who are similar work who want to trade ideas. It makes all the difference. 2) Collaborate, don’t compete. There is plenty of work out there and we all move further and more quickly if we work together. 3) Be open to the universe. I believe good things happen when you put yourself out there — even though what you get back may not be what (or when) you expect it. 4) Get comfortable being uncomfortable. There is a lot of times where the answer isn’t clear and you need to make your best guess. 5) Give yourself grace to make mistakes. See above. You will make wrong moves. You need to make peace with that and realize it's part of the journey. 6) Get a system in place for your financials. This is super boring — but super important. (And, at times, super stressful if you miss something.) 7) Leave your ego at the door. You will get negative feedback. Feel it, learn from it and move on. 8) Attend events. Sometimes my natural inclination is to stay home but I ALWAYS feel energized when I’m learning and with my people. 9) Invest in coaching. Yes, you can learn for free, but coaching will get you there faster and with more confidence. 10) Define success on your terms. This life can be about much more than income. Understand why you are doing this and what success means to you. (It may change over time.) 11) Find your niche. It makes it so. much. easier. to pitch clients and develop proposals. 12) Be open to shifting your niche. As much as I love the simplicity of having a niche, realize that the market and your interests change. Experiment. 13) Don’t compare your journey to others. Comparison really is the thief of joy. And no one has your circumstances, so be proud of where you are. 14) Celebrate the wins. Keep a running list and/or mark the milestones of your business, no matter how small. Some days, you'll need it. 15) Take breaks. One of the best and worst things about LinkedIn is there is no set time off. Don't feel guilty for recharging but instead make it part of your process. 16) Be a lifelong learner. There is ALWAYS something to learn about your niche and running a business. What would you add to the list above?

I've been on both sides of the freelancing world. These 7 freelancing dos and don'ts could save your career!   As a freelancer, a recruiter, and now as the founder of Organaise, I've seen the freelancing world from every angle. Along the way, I've witnessed firsthand what works and what doesn't in the freelancing world.    Here's what you should definitely take care of:   🚫DON'T - Jump into work without clear project scope. ✔️DO - Spend time defining deliverables and milestones before starting. It prevents misunderstandings later.   🚫DON'T - Undervalue your services out of fear. ✔️DO - Research market rates and confidently price based on your skills and experience.   🚫DON'T - Take on every project that comes your way. ✔️DO - Be selective. Choose projects that align with your expertise and career goals.   🚫DON'T - Work without a contract, even for friends. ✔️DO - Always use clear, written agreements. It protects both parties and sets expectations.   🚫DON'T - Neglect your own professional growth. ✔️DO - Set aside time and money for learning new skills and staying industry-relevant.   🚫DON'T - Overwork yourself to meet unrealistic deadlines. ✔️DO - Communicate openly with clients about realistic timelines and manage their expectations.   🚫DON'T - Isolate yourself in your home office. ✔️DO - Network regularly, both online and in person. Connections often lead to new opportunities.   These lessons have shaped how we approach freelancing at Organaise, where we're using AI to streamline the process while still honoring these timeless principles.   What's your most valuable freelancing lesson? #freelancing