Career Roadmap Creation

How do you build a long-lasting career as a freelancer, instead of it being a stopgap or short-lived side hustle? For starters, optimize for interesting, focus on financial longevity, and diversify your offerings. Passing the decade milestone as a freelancer, I’ve identified what’s helped to sustain my interest in the work, continue to drive demand from clients, and other insights that have made self-employment a viable, rewarding path. In my latest for Fast Company, I explore lessons in building a long-term practice based on what’s proven effective for myself and other freelancers. ➤ Niche down strategically so it’s clear what you offer, the types of clients you serve, and what’s unique about your expertise. You can’t be everything for everyone, get specific instead. ➤ Consistently share your ideas publicly, whether through podcasting, a newsletter, or otherwise so clients find you based on your insightful ideas and solutions. ➤ Craft a deployable network. According to Lola Bakare, build relationships with colleagues across sectors, and when the time is right, deploy their willingness to support you. “Be very willing to not just ask for help, but surround yourself in help,” she suggests. You can’t just rely on yourself to make it happen. ➤ Secure social proof. “Over-index on social proof. Early in your career, it's essential to ensure you're being taken seriously,” advises Dorie Clark. “The best way to do this is to gather as much social proof - i.e., easily understood and verifiable symbols of your competence - as quickly as possible.” ➤ Prioritize reliability. “This doesn't mean you have to perform perfectly. It means that you need to show that you value the relationship, and have appreciation and respect for clients who've hired you. That means doing what you've committed to doing, when you've committed to do it, and ensuring open communication around that process,” says Melissa Doman, M.A. ➤ Commit to yearly growth by setting aside time annually to go in-depth on a new learning opportunity that allows you to explore a new area of your business or expand upon an existing offering. ➤ Learn from missteps. “We will all make mistakes, and in my early years, I made a costly error when I relied on a verbal agreement with a friend. That experience taught me the indispensable value of contracts. By clearly defining what our services include—and do not include—we eliminate confusion and potential disputes. It's a preventive measure that has saved me from challenging clients,” added Nicte Cuevas. ➤ Pass on misaligned work. “Many freelancers burn out by working for difficult clients at low rates and then quit. They do this because they need the work — any work. If you can help it, don’t go full-time until you have enough savings to confidently turn work down. Even better, don’t go full-time until your business is threatening to interfere with your job,” suggests Josh Garofalo. Read the article below for all the lessons in more detail. ⭐

𝗛𝗼𝘄 𝘁𝗼 𝗰𝗿𝗲𝗮𝘁𝗲 𝗮 𝗣𝗿𝗼𝗱𝘂𝗰𝘁 𝗥𝗼𝗮𝗱𝗺𝗮𝗽? 🛣 Product roadmaps are not just a list of features. It's not even a project plan. 👉🏻 They are like your product’s GPS that specifies where your product is headed and outlines the vision, strategy and priorities over time. This is where a PM should spend most of their time - strategizing. It helps aligns your team and keeps everyone focused on long-term goals. 🔵 There are different types of roadmaps, each serving different needs: - 𝗦𝘁𝗿𝗮𝘁𝗲𝗴𝗶𝗰 𝗥𝗼𝗮𝗱𝗺𝗮𝗽: This is the high-level view, capturing the product vision and major initiatives for the next 12-24 months. - 𝗥𝗲𝗹𝗲𝗮𝘀𝗲 𝗥𝗼𝗮𝗱𝗺𝗮𝗽: A more granular view, detailing the features and enhancements for the next few releases, typically over 3-6 months. - 𝗙𝗲𝗮𝘁𝘂𝗿𝗲 𝗥𝗼𝗮𝗱𝗺𝗮𝗽: Focuses on specific features, breaking down sub-features, dependencies, and timelines. 🔵 𝗔 𝗽𝗿𝗼𝗱𝘂𝗰𝘁 𝗿𝗼𝗮𝗱𝗺𝗮𝗽 𝘁𝘆𝗽𝗶𝗰𝗮𝗹𝗹𝘆 𝗶𝗻𝗰𝗹𝘂𝗱𝗲𝘀: - Product vision: The goal of your product - Key themes or initiatives: The major areas of focus for your product over time - Timeframes: When you plan to deliver each theme or initiative, such as quarters or releases - Milestones: Key deliverables or checkpoints along the way - Dependencies: Factors that could impact your roadmaps, such as engineering constraints or market conditions 🔵 𝗛𝗲𝗿𝗲 𝗮𝗿𝗲 𝘁𝗵𝗲 𝗸𝗲𝘆 𝘀𝘁𝗲𝗽𝘀 𝘁𝗼 𝗰𝗿𝗲𝗮𝘁𝗲 𝗿𝗼𝗮𝗱𝗺𝗮𝗽𝘀: 1️⃣ Start with the Vision. What is your product’s ultimate goal? Identify the key initiatives that will drive you toward that vision. 2️⃣ Gather input from your team, customers, and other stakeholders. Their insights are crucial for setting the right priorities. 3️⃣ Focus on initiatives that offer the highest value and are most feasible. Prioritize them. The best roadmaps emphasize impact over sheer volume. 4️⃣ Break down your roadmap into timeframes - whether by quarters or releases and identify key milestones. 5️⃣ Choose a roadmap format that suits your product and audience. Whether it’s a Gantt chart, Kanban board, or timeline, keep it simple and focused. 6️⃣ Share your roadmap widely. Ensure everyone is on the same page, from your team to stakeholders and executives. 7️⃣ Iterate it constantly based on new insights and changing market needs. 👉🏻 𝗠𝗮𝗸𝗲 𝘀𝘂𝗿𝗲 𝘆𝗼𝘂 - - Prioritize solving user problems over building specific features. Great roadmaps are outcome-oriented. - Don't reinvent the wheel. Explore resources and best practices from experienced product managers. 𝗣𝗦. Share with people who might need this within your network!

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?

The brutal reason top employees leave startups (and how I fixed it) Startups don’t lose their best people because of salary. They don’t leave because of workload either. The real reason? "They stop seeing the future with you." I’ve seen this happen firsthand. A top performer, fully committed, delivering results… and then one day, they’re gone. When I asked why, the answers were almost always the same: 💬 “I don’t know where I’m headed.” 💬 “I feel stuck.” 💬 “I don’t see growth for me here.” In the fast-paced chaos of building a company, I made a mistake—focusing too much on short-term execution and not enough on long-term career paths for my team. Here’s how I fixed it: ✅ Created ‘Future Maps’ for key employees – We started mapping out potential career paths inside the company. Instead of waiting for them to ask, we proactively discussed their growth every 6 months. ✅ Shifted from ‘What I need’ to ‘What they aspire to be’ – Instead of just assigning roles, I started aligning responsibilities with their bigger goals. ✅ Gave them more skin in the game – Equity, leadership opportunities, and decision-making power. If they feel like owners, they think long-term. ✅ Built an internal hiring pipeline – When people know they can move up, they don’t look elsewhere. Retention isn’t about perks or free coffee. It’s about vision—not just for the company, but for the people building it. Founders: If your best people are leaving, ask yourself— Are they excited about their future with you? #team #success #growth #leadership

THE GREAT DIGITAL DIVIDE In today's rapidly evolving digital landscape, the chasm between those proficient in digital technologies and those without —the digital divide—is widening. This divide not only hampers individual opportunities but also poses significant challenges to organizational growth, talent acquisition, and workforce development. 🖇What happens when there is lack of Digital Adoption? Digital technologies are the backbone of modern economies, driving innovation, efficiency, and competitiveness. Organizations that embrace digital tools and platforms can streamline operations, enhance customer experiences, and unlock new revenue streams. Conversely, those lagging in digital adoption risk obsolescence in an increasingly tech-driven market. A study analyzing data from 59 countries across seven regions between 2018 and 2020 found a positive relationship between economic growth and digitalization. This underscores the critical role of digital adoption in fostering economic development and competitiveness. 🗺Digital Literacy - It is a Non-Negotiable Skill Digital literacy encompasses the ability to effectively and critically navigate, evaluate, and create information using a range of digital technologies. It's no longer a supplementary skill but a fundamental requirement. ♻Impact on Talent Sourcing Organizations seeking digitally proficient candidates often find a limited pool, especially in regions where access to technology and digital education is scarce. This scarcity can lead to increased recruitment costs and extended vacancy periods, hindering organizational performance and growth. 💪Workforce Upskilling: Bridging the Gap Continuous upskilling is essential to keep pace with technological advancements. Organizations must invest in training programs that elevate employees' digital competencies, ensuring they remain competitive and innovative. How can digital literacy be emabraced well? For Individuals: ✔ Take Online Courses – Platforms like Coursera, Udemy, and LinkedIn Learning offer digital skill training. ✔ Practice Hands-On – Use digital tools like spreadsheets, collaboration platforms, and AI-powered apps. ✔ Stay Updated – Follow tech news, attend webinars, and engage in digital communities. ✔ Teach & Share – Help colleagues reinforce learning. For Organizations: ✔ Invest in Training – Provide employees with digital literacy workshops and certifications. ✔ Promote a Digital Culture – Encourage the use of tech tools in daily operations. ✔ Offer Mentorship & Support – Create peer-learning groups to share digital knowledge. ✔ Improve Accessibility – Ensure all employees have access to digital tools and resources. Embracing digital adoption and literacy isn't merely advantageous—it's imperative. How to incorporate a digital mindset? 💡https://lnkd.in/dGGM5vCK #sonniasingh #sonniasinghleadershipcoach #digitalmindset #futureofwork #digitaladoption #workplace #productivity

10 practical freelancing tips that actually lead to long-term growth (And it has worked 100% for me) 1. Position before pitch → Most freelancers rush to pitch before they’re positioned. → Build your online identity like a brand before you send cold messages. → People research you. Be worth finding. 2. Create a ‘freelancing’ origin story → Your why is your weapon. → Most freelancers only talk about what they do and not why they do it. → Write a short story: What made you choose freelancing? → This builds emotional connection and helps potential clients remember you. 3. Screenshots brings trust more than testimonials → Client wins in DMs > polished testimonials. → Start collecting raw proof: WhatsApp, Slack, emails. → Authentic > aesthetic. 4. Create ‘client kits’ → Most freelancers don’t think like businesses. → Design a kit: onboarding doc, SOPs, pricing, delivery timeline. 5. Don’t market like a freelancer. Market like a category → E.g. You’re not a content writer; you’re a conversion partner for SaaS → Rename your role → Rewire how you're seen. 6. Public wins = Private leads → Post your process. → Your before-after results. → Even your thought experiments. → Being “seen working” drives DMs more than being “perfect and silent.” 7. Ask your client what made them choose you → Then use their actual language in your next LinkedIn bio/intro line → No copywriter knows your client like your client. 8. Never negotiate deliverables in DMs → DMs are for intent. Send a “calm confidence” proposal after. → Looks more pro. Makes them 𝘱𝘢𝘶𝘴𝘦 before ghosting you. 9. Show proof of personality → People work with humans, not PDFs. → Share your quirks, principles, values. → It builds invisible loyalty even before the first call. 10. Build a ‘Brand Bank’ Start a folder with: → Wins → Failures → Client quotes → Story prompts → Hooks you wrote It’s your personal brand library. Every post = a deposit.

Digital Literacy and Digital Mastery are entirely different things. You don't need mastery to be Digitally literate and have a Digital Mindset. All you need is 30% competency in a handful of Technical topics. Tsedal Neeley and Paul Leonardi have created this amazing framework ---The 30% Rule to Digital Literacy, in their book “The Digital Mindset”. Here is what it means. To build a Digital Mindset, you need to have 30% competency in three areas — Collaboration, Computation, and Change. 1/ Collaboration: The first element is to learn how to collaborate with the Machines. For instance, how do you collaborate with AI tools to make yourself and your organization more productive? Building enough knowledge to be able to confidently speak about technology and what it can unlock for your organization. Then how do you interact and innovate using technology? This requires only 30% knowledge of different ML and AI techniques. 2/ Computation: Understand 30% of how technology is collecting, categorizing, consuming, and storing the data. This means basic knowledge of different data analyses and statistical measures. You don’t need to become a statistician, but knowing what different terminologies mean when presented, will make you more confident in making data-driven decisions. 3/ Change: In the context of Digital Transformation, adapting to change is vital. How do you create a culture of change, experimentation, and psychological safety to drive digital adoption in your organization? Again you don’t need to become a project and change management expert, but understanding and acknowledging what is needed to support a culture of change is the key here. 🌐 The beauty of the 30% rule is that it simplifies digital literacy making it an achievable goal for anyone willing to invest in their digital skills. Remember, it's not about mastering every digital tool or trend but about being competent and confident enough to navigate the digital aspects of our world. Let's embrace this mindset and empower ourselves to thrive in the digital age! Share your thoughts in the comments below. #DigitalLiteracy #DigitalMindset #FutureOfWork #professionaldevelopment #DigitalTransformation ——— I regularly write and speak about: 👉 How digital disruption is reshaping the workforce of the future. 👉 Simplifying and automating core processes. 👉 Empowering the future workforce with Digital skills and even more importantly…mindset! ✅ Follow me or connect for more on this.

Are You Charting Your Path or Just Wandering? I often meet people with a vague idea of where they want their career or life to go, yet they spend no time mapping out their journey. As a result, they flip-flop from one opportunity to the next, without a clear direction. Years ago, I dreamed of traveling with work, raising three children, driving a specific car, and living exactly where I wanted. I made a plan. That plan didn't just give me clarity, it gave me a laser focus that was crucial in achieving those dreams. Now, I'm crafting an even more ambitious plan because if there's one thing I've learned, it's that I wasn't ambitious enough the first time around. The best advice I can offer anyone looking to find a new role, make an international move, or take the next step in their career is this: Reverse engineer your goals. Identify your target, plot the steps to get there, and seek mentors who've already walked that path. They can help accelerate your journey. MCG Talent

Grateful for the opportunity to share my story in this podcast and how a design approach can help Singaporeans plan for longer, more fulfilling careers. As industries evolve and populations age, more people will find themselves at the crossroads of career pivots and reinvention. Many of us will navigate a second or even third careers. The rapid pace of technological advancements and shifting job markets makes it increasingly difficult to predict what’s next. To tackle this “wicked” challenge, applying design thinking can help shape your next career chapter. In the context of career transitions, design thinking encourages reflection on strengths and passions while providing a structured yet flexible way to explore new possibilities. The first step in planning for a late-career transition is self-empathy—stepping back to reflect on what truly brings you joy, what you excel at, and where your values align. This can uncover unexpected opportunities. Ask yourself: - What do I enjoy doing? - What are my strengths, and how can they transfer to a different industry? - What unique experiences do I bring to the table? After reflection comes prototyping—experimenting in a low-risk, manageable way with different roles or industries to see what resonates before making a full commitment. Fractional roles and volunteering with cause you care about are great ways to stay engaged, learn, and discover what’s truly meaningful. I’ve personally benefited from this process, transitioning from two decades as an entrepreneur to my current roles as an Entrepreneurship Trainer and Advisor to budding startups. If you’re curious about designing your next career move, feel free to reach out—I’d be happy to chat and share more. https://lnkd.in/gn3_b_GX

A simple infographic I put together last night breaking down the creative macroeconomics of the past and upcoming 10 years in the industry... The value we create through design is set to keep growing - no doubt about it. More companies and influencers are investing increasingly in brand. That’s the good news. The not-so-good news? Fewer creatives are driving most of the value. Robots are here, handling a lot of routine tasks. While they’re not yet streamlined for everyone (primarily creatives at the moment), as they become mainstream and more user-friendly, tasks that once took 10 days will be completed in hours, inevitably driving down prices due to simple market trends. Some of this is already happening. As machines take on more and fees decline, the industry will be dominated by commodity creatives. And a tiny group of highly skilled creatives with sharp strategic insights (the work machines can’t replicate) will see disproportionate rewards, creating a significant gap in wealth and opportunity in the creative economy. How to make sure you're in the tiny pink dot in the top right corner? We are all trying to figure it out but here are some tips: - Listen. Listen. Listen. - yep, listen to your clients/users. Ask. Hear what they are not saying. - Build strategic thinking - Connect design, business goals and strategy. Forget the idea that you do only one part of the process. You are master of one, but your part doesn't exist on its own. - Leverage Data - stop guessing. Use real data to inform creative decisions. Do your own research. Understand competitors and market trends before jumping to the drawing board. - Focus on Brand Storytelling: Master storytelling to help brands communicate unique narratives that go beyond visuals. - Enhance Your Soft Skills: Build strong communication, negotiation, and client relationship skills. You need to be able to sell your crazy ideas to make them alive. #creative