We've all been there.   We make a mistake in our business. And for days or weeks we get caught up in a mental loop of "what if..." and "if only..."   Regret can feel overwhelming, but the real problem is not just the mistake. It's how we respond to it.   In this week’s short episode, I explain 3 mistakes most of us make when trying to deal with regret — and how we can deal with the issue more productivity.

Have you ever felt ready to give up on prospecting because you weren’t seeing results? You’re not alone. Many freelancers quit just before the seeds they’ve planted begin to sprout. In this episode, we explore why consistent prospecting is crucial, even when it feels like nothing’s happening.   In this episode, I explain why timing is everything in prospecting. I share powerful analogies and strategies to shift your mindset. And I offer a practical, habit-building approach to make prospecting a seamless part of your routine. If you’ve ever doubted the effectiveness of your outreach efforts, this episode is for you.   What You’ll Learn Why only 5-10% of prospects are ready to say "yes" at any given time. How to stay consistent even when it feels like you're getting nowhere. The "garden analogy" for understanding the slow but steady process of prospecting. Why a mediocre message at the perfect time can outperform a perfect message at the wrong time. How to build a prospecting system that works for you, using small, actionable steps.   Key Takeaways Timing Beats Great Copy: Even great emails won’t land if the timing isn’t right. Learn to accept this reality and focus on staying visible for when the timing aligns. The Dip is Your Friend: Seth Godin’s concept of "The Dip" explains why most people quit right before they succeed. Don’t be one of them. Consistency Beats Perfection: Imperfect but steady action is more effective than sporadic perfection. Build habits that make prospecting automatic. The Four Laws of Prospecting Habits: Make it Obvious: Create cues and systems to make prospecting part of your daily routine. Make it Attractive: Pair prospecting with something you enjoy and celebrate small wins. Make it Easy: Break down outreach into manageable steps, like sending two emails a day. Make it Satisfying: Reward yourself for consistent effort, not just responses.   Actionable Exercises Start Small: Commit to sending just 2-3 prospecting emails a day for the next 30 days. Track Consistency: Use a simple tracking sheet to monitor your efforts daily. Celebrate Wins: Keep a journal of small victories, such as completing your outreach for the day. Try the “Garden Perspective:” Imagine each email as a seed—focus on the process, not immediate results.   Memorable Soundbites "A mediocre message at the perfect time beats a perfect message at the wrong time." "Success in prospecting isn’t about perfection—it’s about showing up consistently." "Prospecting is like planting a garden. The magic happens beneath the surface before you see results."   Deploy a Powerful Prospecting System in Just 21 Days I’m starting a new prospecting workshop next week. We’re going to work together over 21 days (Mon-Fri only) to help you implement effective prospecting techniques and habits that actually stick. We’ll roll up our sleeves and actually create your prospecting plan and assets together. And I’ll be there every day to give you direct and personal feedback.   You’ll implement the material day by day, one baby step at a time. And you’ll come away with everything in place, all ready to go.   Would you like to join us? Email me at [] and I’ll respond with all the details.

Happy New Year!   If you're looking to make 2025 one of your best years yet, I have a different approach for you to consider...   Start with zero. And by zero, I mean absolutely nothing.   Doing so will help you accomplish more... and faster.   That’s the topic of this week’s short episode below.

Freelancing can be an exhilarating journey — building a business from scratch, gaining financial freedom, and securing prestigious clients. But what happens when the work that once lit you up begins to feel hollow?   If you've ever wondered if there's more to your career than just success, this episode is for you.   In today’s show, we explore the concept of “Halftime,” a mid-career pivot that shifts your focus from external achievements to deeper personal fulfillment and significance. Drawing from personal experiences and the transformative lessons of Bob Buford’s book Halftime: Moving from Success to Significance, this episode invites you to rethink your path and take actionable steps toward a more meaningful second act.   What You’ll Learn The concept of Halftime and why it’s a proactive, purposeful pivot—not a reactive crisis. How to identify the signs that you’re ready for a career transition. Strategies to realign your work with your core values and personal goals. Practical ways to leverage your existing skills and experience to build a meaningful legacy.   Key Insights and Takeaways Why Halftime Matters for Freelancers As a solo professional, you don’t have a corporate roadmap for navigating career transitions. The freedom to chart your own course is both a burden and a gift. Halftime provides a framework to help you pause, reflect, and realign your business and life in a way that serves your higher purpose.   Recognizing the Need for Change Do any of these resonate with you? You’ve achieved financial milestones but feel unfulfilled. Burnout or fatigue has crept in, leaving you questioning the purpose behind your work. The creative spark that once energized you has faded. These are common signals that it’s time to pivot toward significance.   The Pillars of a Successful Halftime Journey 1. Success Without Significance is Hollow Many freelancers measure success by income, clients, or accolades. But these metrics alone often lead to burnout and dissatisfaction. Reflect on moments in your career that felt truly meaningful. What made them stand out? Practical steps: Revisit your core values and align them with your business goals. Conduct a career audit to identify areas of fulfillment and disconnect.   2. Build on Your Foundation to Create Your Legacy Halftime isn’t about starting over; it’s about using your experience and skills as a launchpad for the next chapter. What does legacy mean to you? It could be as simple as meaningful client work or as ambitious as creating a program that outlasts you. Envision your ideal second act. What kind of work excites you? How can you structure your career to reflect your values?   3. Embrace Experimentation and Small, Purposeful Steps Transitioning doesn’t require a drastic overhaul. Start with small shifts: Say yes to projects that align with your values. Begin phasing out work that drains you. Introduce joy and creativity back into your routine with passion projects. Create margin in your schedule for reflection and exploration.   Actionable Exercises Identify Your Big Why Ask yourself: What matters most to me at this stage of my life and career? Write down 3-5 values that guide your decisions and revisit them regularly. Conduct a Legacy Audit Reflect on your career and identify moments of significance. Ask: How can I create more opportunities for this kind of work? Try the “Joy Alignment Check” List current clients or projects. Which ones energize you? Which ones drain you? Take one small action this week to bring more joy into your work. Draft Your Legacy Statement Example: “In the next 10 years, I want to be known for helping [audience] achieve [outcome] through [method].” Use this statement as a guidepost for decisions moving forward.   Listener Challenge This week, carve out 30 minutes for a personal “vision session.” Ask yourself: What would my career look like if it fully aligned with my values? What small changes can I start making now to move closer to that vision?   Memorable Soundbites “Success without significance is ultimately unfulfilling.” “Your first half built the foundation; your second half builds the legacy.” “This isn’t about starting over—it’s about leveraging everything you’ve built in a more meaningful way.”   Join Me for a Transformative Coaching Experience If today’s episode resonated with you, I have an invitation. Next month, I’m hosting an 8-week small-group coaching program designed for freelancers and solo professionals ready to embrace their Halftime journey.   We’re going to work together over the course of 8 weeks to write a new story for yourself — one that’s unique to you and will enable you to navigate through this fog of doubt and overwhelm.   I'll provide a supportive environment where you can engage deeply with your professional challenges. Together, we'll tackle tough questions that will help you discover the answers you need to confidently navigate your future.   This journey could very well be the catalyst for that profound transformation, helping you navigate through uncertainty with newfound clarity and confidence.   The program is intentionally small and deeply personal. If you’re in your 40s, 50s, or 60s and ready to explore your next act, email me [] with “CLARITY” in the subject line. I’ll reply with all the details.

Do you ever feel like you’re constantly dealing with the same frustrating challenges in your business?   Maybe you get stuck managing messy revisions from unexpected sources, or a client keeps hitting you with last-minute rush work.   In this episode, I discuss how we often react to these situations rather than respond thoughtfully—and why that difference matters.   We explore two key steps to improve your responses:   Taking a pause before making decisions. Asking yourself better, more open-ended questions that lead to more productive solutions.   This episode is all about how the quality of your internal questions can shift your perspective and help you navigate difficult situations with clarity.   Listen below or subscribe to the podcast on your favorite platform.

As freelancers, many of us crave the freedom to explore new places without the financial burden that travel can bring. But what if you could fly in luxury without spending a fortune? That's where points travel comes in, and today's guest is a true expert in this game. Spencer Howard, the mastermind behind , has helped countless people book premium travel with points instead of cash—making dreams of business and first-class travel a reality. In this episode, Spencer shares his journey from a political career to building a freelance writing business to becoming a full-time freelancer in the world of points and miles. He dives deep into the strategies freelancers can use to leverage credit card rewards and optimize points for travel, breaking down complex topics like transferable points and airline-specific credit cards. And he explains how to do this without getting into debt or paying credit card fees that don’t make sense. I learned a lot from this conversation. I realized that many of my hang ups about points travel were unfounded. And I discovered that I’m actually making some pretty big mistakes with a strategy I assumed was getting me huge travel perks (but it’s really not a great value!). If you love to travel, you’re going to find several actionable tips on how to maximize your points, avoid common pitfalls and plan your next dream trip—all without breaking the bank or getting into debt. Enjoy!

Have you ever had a client, prospect—or even an acquaintance—ask to "pick your brain"?   At first, it might feel flattering. But after the fourth or fifth time, it starts to feel like a burden.   You feel taken advantage of.   In this short episode, I talk about how I changed my approach to these requests. Instead of making excuses or feeling resentment, I started charging for “brain picking” sessions—and it completely transformed how I handle these situations.   I walk you through how I reframed these requests into a structured offer, how I set the price, and how you can do the same to ensure that clients and prospects value your time and expertise.   It doesn’t matter what type of work you do as a solo professional. If you get these requests regularly, this episode will give you practical tips on how to handle them with confidence.

Most freelancers and solo marketers focus their marketing efforts on prospecting, networking, or LinkedIn.   But guesting on podcasts that your target audience listens to? Not so much.   And that’s too bad, because appearing on podcasts can be a powerful way to build your brand, meet and network with great people, generate leads, and establish yourself as a thought leader in your market.   In this episode, I sit down with Angie Trueblood, a seasoned podcast publicist, to explore how freelance writers and solo marketers can harness the power of podcast guesting.   Angie shares her unique journey into the world of podcast publicity and breaks down why being a guest on the right shows can make a huge positive difference in your business. We dive deep into actionable strategies, including:   Why podcast guesting is an underused but highly effective strategy for freelancers How to identify the podcasts that will bring real value to your business Insider tips on crafting a genuine, irresistible pitch Practical advice on preparing for your podcast debut to maximize impact How to track and measure the success of your podcast guesting efforts   Whether you’re looking to expand your client base, increase your visibility, or simply explore new avenues for growth, Angie’s insights will open your eyes to the untapped potential of this marketing strategy.

A growing number of writers are incorporating AI tools into their workflow.   Those who’ve kept an open mind and experimented with different approaches and ways to increase their productivity and scale their creativity have seen remarkable improvements in both the quality and quantity of their work, allowing them to stay ahead in an ever-evolving industry.   The current models are powerful out of the box. But what if there was a way to take things a step further and create personalized AI tools tailored to your unique needs?   In this episode, I sit down with Erynn LaFlamme, founder and CEO of Ethic Agency, a marketing agency based in Metro Atlanta. Erynn and I discuss how writers can harness the power of custom GPTs to handle nuanced parts of their client workflow.   Erynn has become an expert in using AI for content creation, and she walks us through the process of building Custom GPTs and shares real-world examples of how her team is leveraging this technology to produce better work.   We dive deep into:   The difference between Custom GPTs and using standard ChatGPT Key steps involved in creating GPTs for specific clients Challenges and ethical considerations in AI-powered workflows How to refine and improve Custom GPTs over time Deciding when to use a Custom GPT versus a general AI tool   We also explore what this means for the future of freelance writers and content professionals—will AI replace us, or will it become an essential tool in our toolkit?   Whether you’re curious about integrating AI into your business or looking for ways to refine your processes, this episode offers some very practical ideas, insights and tips.

I was doing an exercise the other day where I looked back over the past 3 decades of my career to think through every major breakthrough I had and every big move I made.   Not only was this a fun trip down memory lane, it also made me realize a few very important things.     One of them is that nearly every breakthrough happened during a very challenging moment in my career. And in a few cases, they happened when I was desperate—when I was in a very tight spot and desperately needed things to turn around.   And that got me thinking, “You know ... desperation can lead to some very powerful breakthroughs!”   That’s the topic of this week’s short podcast episode below.