Freelancing offers freedom, but it also comes with its fair share of struggles—unstable income, no safety net, and difficult conversations about pricing.
In this episode, we speak with Adrian Ashton, a freelancer with over 20 years of experience in enterprise, social impact, and policy development who guides organizations and individuals through uncertainty and helps them see the light at the end of the tunnel 🤩
From this episode, you'll learn:
✅ Why financial insecurity is a major challenge for freelancers.
✅ How to protect yourself financially, emotionally, and physically.
✅ The real reason undercharging can cost you clients.
✅ How to approach pricing discussions with confidence.
✅ Why freelancing is like a poker game—and how to play it right.
Watch now and take control of your freelance journey! 🚀
🎧 Or listen to it here on Spotify
The biggest freelance struggle: no security, no guarantees
One of the toughest realities of freelancing is the lack of stability—there’s no guaranteed work, no employer benefits, and clients who might cancel projects or delay payments.
🔹 No income security – Projects can be canceled anytime, and clients may not always pay on time.
🔹 No health or welfare safety net – Unlike full-time employees, freelancers must handle sick days, vacation, and health insurance on their own.
🔹 No long-term stability – Freelancers must constantly find new clients, negotiate contracts, and manage unpredictable work cycles.
💡 Solution: The guest emphasized the importance of saving early to create a financial buffer and investing in private health insurance to ensure long-term security.
How to protect yourself as a freelancer
Self-protection is key to survival and thriving as a freelancer.
Here are some strategies shared in the episode:
✔️ Financial Protection: Build a safety net by saving several months’ worth of expenses.
✔️ Health Protection: Invest in health insurance to prevent disruptions in case of illness.
✔️ Mental Well-being: Regularly check in with a counselor and engage with freelancer communities.
✔️ Community Support: Join online groups like Freelancers Unite UK, Being Freelance, and IPSE to avoid professional isolation.
💡 Pro Tip: The guest introduced the idea of “convivial procrastinated drinking” (CPD)—grabbing a casual drink with fellow freelancers to discuss wins, failures, and problem-solving strategies in a relaxed setting.
The most time-consuming part of freelancing
Beyond doing the actual work, freelancers spend a huge amount of time on other aspects of running their business:
🔹 Client acquisition & admin work – Searching for clients, handling invoices, negotiating contracts.
🔹 Personal obligations – Many freelancers juggle caregiving, family responsibilities, and personal commitments.
🔹 Continuous learning – Freelancers must constantly upskill to stay competitive in the market.
💡 Solution: Use time-blocking techniques, but be flexible enough to adjust when life happens.
The most nerve-wracking part: talking about pricing
Freelancers often struggle with setting and negotiating rates. Many fear losing clients by charging too much or losing credibility by charging too little.
🔹 Undercharging makes you look inexperienced – Clients may assume you’re not good at what you do.
🔹 Overcharging without confidence can push clients away – If you don’t back up your rates with value, clients may reject your offer.
💡 Solution: Benchmark your rates by researching freelancer platforms like Juno, IPSE, and industry-specific communities.
Freelancing is like a poker game—are you playing it right?
Pricing and client negotiations often feel like a high-stakes poker game. The guest shared a powerful insight:
🃏 "Sometimes, I let the client decide what to pay me at the end of a project—and every single time, they pay me more than I expected."
This strategy builds trust and transparency in client relationships, though it’s not for the faint of heart!
💡 Lesson: Confidence in your value leads to better pricing discussions—and better-paying clients.
Top 3 lessons every freelancer must know
1️⃣ Always have backups – Your tech will fail at the worst time. Be prepared.
2️⃣ Budget aggressively – Plan for both business and personal expenses.
3️⃣ Redefine work-life balance – Without traditional benefits like paid holidays, freelancers need to create their own self-care structure.
💡 Freelancing isn’t just about work—it’s about designing a sustainable lifestyle.
If you were starting freelancing today, what would you do differently?
Answer: Charge more from the start.
🎯 Charging too little leads to financial struggles and lost opportunities.
🎯 Clients often assume low rates mean low quality.
🎯 Raising rates attracts better clients who respect your expertise.
💡 Pro Tip: Know your worth, benchmark your rates, and never be afraid to charge what you deserve.
TL;DR
✔️ Build financial security with savings and smart budgeting.
✔️ Protect your health and well-being—both physically and mentally.
✔️ Be confident when discussing rates and avoid undercharging.
✔️ View freelancing as a game of strategy—learn how to play it well.
✔️ Join freelancer communities to avoid loneliness and get support.
Quotes from this conversation:
1️⃣ “Freelancing means no guaranteed work, no guaranteed income, and no safety net—so you have to build your own.”
2️⃣ “If you undercharge, clients will question your professionalism. If you charge more, you’ll attract better clients who respect your work.”
3️⃣ “The biggest mistake I made? Not charging enough from the start. It cost me financially and lost me opportunities.”
4️⃣ “Freelancing is like poker—you need to read the table, know when to push, and when to walk away.”
5️⃣ “As a freelancer, you’re not just working for yourself—you’re also your own safety net, accountant, negotiator, and therapist.”
