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
- 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.
- 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?
- 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 [ ed@b2blauncher.com ]with “CLARITY” in the subject line. I’ll reply with all the details.
The notes that follow are a very basic, unedited summary of the show. There’s a lot more detail in the audio version. You can listen to the show using the audio player below. Or you can subscribe on Apple Podcasts, Spotify, Stitcher, Google Podcasts, Amazon Music or wherever you listen to podcasts.
Key Topics and Bullets:
- Midlife crisis due to personal/professional events
- Use of a coach and “Halftime” by Bob Buford for self-discovery
- The Halftime Concept
- Transition from success to personal fulfillment
- Proactive midlife journey without organizational guidance
- Economic Changes and AI
- Impact on freelancers reconsidering career paths for satisfaction
- Encouragement for self-reflection and career reevaluation
- Core Pillars of the Halftime Journey
- Pillar 3: Leverage Achievements
- Gradual Shift to Values-Aligned Work
- Experimentation and Guardrails
- Life Beyond Business
- Legacy and Phased Transition
- Client/project audit for energy drainage
Timestamp Overview:
00:00 Ed– I want to open this up with a story of a freelance copywriter. Let’s call her Kelly. That’s not her real name. Who was earning over $230,000 a year in income. Now that’s net before taxes. So that’s pretty much after her expenses. She wasn’t outsourcing any of the work. She was doing it all herself. And Kelly had everything she thought she wanted. She had great prestigious clients, steady work, fantastic income. But sitting in her home office one evening, as she stared at another pile of client briefs, she realized something was missing. The work that had excited her 12 years ago now felt hollow. And she was really kind of at a crisis because this is everything she wanted. She, 12 years before, had she seen herself at this enjoying this level of success, she would have been thrilled.But here she was enjoying everything she had described she wanted out of her business, and she just wasn’t feeling it. I’m seeing more of what Kelly is experiencing than I ever have in my nearly 20 years of being fully self employed. And if you’re in your fifties or sixties, even in your forties, especially late forties, there’s a good chance you’re feeling something similar right now. I found myself personally at a crossroads in my own life and my own career. Been really grappling over the past few years with feelings of resistance and really pondering what might be next for me. This journey and these questions started a little late in life for me. I’m in my early fifties, and this started about 2 years ago. And I remember I remember some of the triggers, some of the signs that it had actually been there a little bit longer, but I wasn’t paying attention.
05:05 Ed– So the pause button was key in and it was key because deep down inside, I knew I needed to step aside and take a closer look at what I was doing. And I just wasn’t listening to that voice. So when my operations manager left, all this kind of came crashing down on me. It all came to a head. And even then, even after stepping aside and looking at this a little bit more critically, honestly I just wasn’t sure what to do. I did start a very helpful process of self discovery with my own coach, and that started giving me some serious clarity. Now I’m gonna fast forward a little bit to about a year ago. So this is early 2023. I had made some headway. I had gotten some clarity, but someone recommended a book to me. And this was somebody who didn’t really know what I was going through at the time. Somebody who didn’t really know me that well. In fact, somebody who didn’t really know me. This is at an online forum. And I was asking a totally unrelated question, and they recommended a book that they thought would help me on a very specific question. And frankly, it was about retirement and investing.
06:38 Ed– And my interest really on this topic was more academic and based on a personal curiosity about the subject. But this person’s recommendation sent me down a bit of a rabbit hole. The book that he recommended is called halftime, moving from success to significance. And it’s by the author, Bob Buford. And this concept of halftime is a metaphor. It’s a sports metaphor referring to a pivotal midlife transition where individuals just start shifting their focus from external success to deeper personal fulfillment and significance. And this is meant to be halftime is meant to be an intentional pause. And it’s different, markedly different from a mid career crisis because a crisis feels reactive and powerless.
07:44 Ed– But this halftime concept that Buford was describing was very different from that. It was really more of a proactive and purposeful process where you’re in control. So what does this have to do with what we do and why would this matter specifically for freelancers? Well, I believe that and I have seen and I’ve been at this for about 20 years now, that solo workers don’t have a road map or organizational guide for this kind of transition. The burden and the freedom of direction is entirely ours. We get to make these choices, which is wonderful. But because we’re completely on our own and we get to chart our own course and really decide everything about what we do, that can be a burden as well. There’s no career path. There’s nothing kinda defined for you.
12:00 Ed– You analyze. You strategize. And you think about it from a totally different point of view because you’re not out there in the middle of the field under all that pressure. And based on those decisions, he can come out to the playing field and play that second half of the game. Another metaphor, if you don’t like a sports metaphor, could be that this is the process of an intermission. And, you’re gonna go back out there after some serious reflection, and go live your second act. So whatever it is, I’m gonna stick with halftime here today just so I don’t have to go back and forth. But the main idea here is that there needs to be some sort of pause that we all get to a point where we need to hit that pause button so we can step aside and reflect on where we are right now.
17:02 Ed– Burnout. Burnout or fatigue. And especially if you’re feeling burnout and fatigue despite achieving your goals or even exceeding your goals. You know, when you start asking this question, what is all this for? Right? When that starts popping up, when you look at what you’ve achieved and the period of feeling thrilled or ecstatic about what you’ve done is now much shorter. You know? We’re now at just you you get kind of a quick high that lasts 5 minutes, and then reality kinda sets in about, well, you know, what is I’m not really excited. This doesn’t really mean that much to me anymore. Then those are clear, clear signs. A lack of joy or creativity in your work
17:56 Ed– Maybe if you don’t care for it anymore. A coaching client confessed to me last year that content marketing just doesn’t make the world a better place. And that content was creating all kinds of internal conflicts for her just as she created it for clients because she thought in her mind, this felt like something that was actually making the world worse. And, you know, my first reaction when I heard that was, well, and I didn’t say this to her, but she’s really lost perspective here. But it didn’t take me long to realize that she had a point. I’m not saying she’s right or she’s wrong. It’s really about how she’s feeling about this. And this is clearly someone who is just hitting a wall and needs to start taking a different look at what she’s doing.
23:27 Ed– Moving on to pillar number 2. Pillar number 2 is the idea that your first half of your work life or career built the foundation, but your second half should really build your legacy. The skills, the networks, the experiences from your first half are invaluable assets. And you need to recognize that you can still and should leverage all of those in your second half. Half time in the process of taking this time, this intermission, halftime, whatever you wanna call it, isn’t about starting over. It’s just really about leveraging everything you’ve built to this point to now figure out your next chapter. You have a whole set of powerful tools that you can apply differently now.
27:17 Ed– So how could you start building your legacy again? This is not an overnight thing. Well, I think it really starts by envisioning your second act or the second half of your life, of your career, of your work. You know, and ask yourself a different set of questions. So for example, what kind of work or clients would feel like a legacy for you? What would that legacy have to come from your traditional work? Or could you somehow leverage your core gifts and talents in some other way? You know, I think we take our skills and our abilities and our talents for granted. We do this work for so long, whether it’s copywriting or content marketing or content strategy, whatever it might be, public relations. We do it. We do it well. In fact, the better you do it, the more you take it for granted.
30:04 Ed– You know, I I think this world is designed to prepare us for maybe the financial aspect of a second or third act in our lives, But it does a really, really poor job to help prepare us for how we’re going to live meaningful lives in the second, third, and fourth act of our lives. So just some food for thought there. You don’t have to retire in order to make these shifts. I see this as an off ramp or an on ramp depending on how you look at it. Where you do, how you do it with whom you do it evolves little by little by little. You don’t have to wait until you’re completely retired, so to speak, in order to make these shifts. In fact, I think that’s a huge mistake. This overnight shift, it
31:43 Ed– You could do this for other people, other groups, other industries. So I just wanted to open that up and get you thinking about that a little bit more. Building a team or a collaborative structure to amplify your impact or shifting your focus to projects with either social or community or industry significance. You know, these are things you can start thinking about right now and maybe testing at a small scale because, you know, not only is that lower risk, but you may not have the time to make something really big or invest in something completely new right now in terms of time and financial resources. But you can certainly start thinking about it and you can start experimenting. You could start putting some feelers out there. So what might that look like? You know, what could you do? Where do you even start? So let me give you a reflective exercise here. I want you to try and write your legacy statement for the next decade.
37:19 Ed– Look, we all have to keep the lights on. Right? We all have to pay our bills. But I think many times we use that as a crutch. I think many times we go ahead and take on clients and opportunities by convincing ourselves that, well, I, you know, I have to be responsible. And this is what I have to do when I have to say yes. When in reality, you don’t necessarily need to say yes. You know? And this is why it’s so important to take the time to get clear on these things because that’s what’s gonna give you direction and help you make better decisions. And you don’t have to make these changes again overnight.
41:36 Ed– But in the past you would have glossed over it and you would have just listened to them, you know, catch yourself feeling that nudge inside you that says, hey, that sounds like something I might be able to get involved with. And you don’t have to commit to your friend. You know? But maybe that the next move there would be, hey, tell me more about that. So what are you doing with that organization? How are you involved? What are you guys trying to accomplish? So probe a little further. When situations come up that, you know, your intuition is telling you, you might want to learn more about, listen to your intuition. Also start to gradually phase out work that drains you or feels misaligned. And again, I know what might be coming up for you when you hear that. It’s like, well, Ed, that sounds, you know, that must be nice that you could do that, but I can’t afford to do that.
43:51 Ed– You could create quarterly vision days to reevaluate your goals and your progress. Or you could plan a semi-annual personal retreat in a remote location for a couple of days. Where you plan ahead and you give yourself some really good questions and food for thought to explore and to unpack over those 2 days. Prioritize Joey. That would be another really important piece of advice that I would give you. So one example would be reviving passion through personal projects. A freelance content writer, for example, decides to set aside 1 morning per week to create a newsletter focused on a personal interest, like sustainable living or travel writing. And she finds that this project allows her to explore a topic she loves without client constraints and allows her to showcase her unique voice and creativity.
47:27 Ed– I want you to take a moment to think about your current clients or projects. And ask yourself, which one brings me the most energy and excitement? At the same time, I want you to ask yourself, which one feels the most draining or uninspiring? Next, I want you to identify one small action you can take this week to bring a little more joy into your work. So for example, maybe spend an hour brainstorming ideas for a passion project, Or maybe reach out to a client or prospect whose mission excites you. Yeah. Are some of these things gonna be scary? Probably. But again, we have to start somewhere. It’s gonna require even the small actions, the small steps are gonna require some courage. And then I want you to block out 30 minutes in your calendar within the next week to re
51:35 Ed– Now before I sign off, I have an invitation for you. If you find yourself at a similar crossroads, struggling to find your way forward, I might be able to help. I’m about to coach a small group of solo professionals who are seeking a renewed sense of purpose. They’re seeking a clear path ahead and the confidence to make a real breakthrough in their business, in their work, in their lives. And starting in January and over the course of 8 weeks, I’m gonna provide a supportive environment where you can engage deeply with your professional challenges. Together as a small group, we’re gonna tackle tough questions that are going to help you discover the answers you need to confidently navigate your future. So we’re gonna enter in a way this intermission. We’re gonna start entering this halftime process.
53:58 Ed-So not somebody who’s looking for answers on a silver platter. I’m looking for people who understand that they’re gonna have to do the work and unpack things on their own with my guidance and leadership so that the right solutions, ideas, and direction will emerge for them. I’m looking for people who are willing to confront tough questions and explore underlying issues and who are open to discussing their challenges, their fears, their aspirations candidly and authentically with me and a very small group of like minded peers. People who are at the same stage of life going through the same challenges and issues. They’re all gonna be unique, of course, and, you know, what specifically they’re dealing with. But at the core, we’re all gonna be in the same phase of life. I’m looking for people who are friendly and coachable. You know, this is an 8 week journey.
55:50 Ed– But this is really an experience that’s designed for those of us, who are ready for and maybe even way overdue for this halftime process. I’m calling this experience from chaos to clarity, an 8 week journey for freelancers seeking peace and direction in their career. I’ve opened registration already, and I got a few spots left. If what I’ve shared here today is resonating with you, if you’re finding yourself at a crossroads in your career, this might be exactly what you’ve been searching for. And I’d love for you to consider joining us. I don’t have a sales page for this. I’m keeping this relatively low key, but I have a PDF that I can send you with all the details. And if you want that, just simply email me, ed@b2blauncher.com.
By the way… whenever you’re ready, here are 4 ways I can help you grow your freelance business:
1. Claim your free book:
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3. Work with me for 90 days
Need a trusted “sparring” partner to tackle your most pressing business challenges? I occasionally offer an intensive 90-day coaching program for freelancers at all income levels. We work together 1-on-1 to identify your most critical business obstacles, come up with innovative solutions and develop a customized, actionable plan. Email me at ed@b2blauncher.com with “90-Day Accelerator” in the subject line to learn more.
4. Banish 6-figure burnout
One of my core specialties is helping 6-figure freelancers earn more in less time with less stress. If you’re at that income level but you’re burning out and want to create a business that actually serves you, let’s connect. Email me at ed@b2blauncher.com and put “Boardroom” in the subject line and I’ll get back to you with more details.
