The Freelance Insider Show

Al Calder
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  • Entrepreneurship
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The Freelance Insider Show gives you a real-world look at what it takes to build and grow a successful freelance business. Whether you're just starting out or leveling up, each weekly episode delivers practical tips, strategies, and no-fluff advice you can actually use — from landing clients and setting your rates to managing burnout and staying motivated. 🎯 Ready to hit reset and build a freelance business that works for you? Grab your free Freelance Reset Checklist at https://alcalder.eo.page/hq52z and start strong. Let’s get started!

  1. 3d ago

    How to Build a Freelance Business by Thinking Differently (Not Following the Rules)

    What Can You Actually Control in Your Business? What if the biggest thing holding your business back isn't the economy, the competition, or the clients you're trying to attract—but the things you're not doing? In this episode of The Freelance Insider Show, I’m joined by Major Hillard, entrepreneur and real estate investor, to talk about building a business, developing systems, playing to your strengths, and focusing on what you can actually control. Major shares how he got started while working three jobs with just $1,500, and how a book called "Deals on Wheels" by Lonnie Scruggs introduced him to mobile home investing. We also get into the lessons he's learned along the way and why building systems and learning to delegate are essential if you want to grow beyond simply creating another job for yourself. Whether you're a freelancer, solopreneur, or small business owner, there are some valuable lessons here about taking responsibility, making better decisions, and building a business that can grow without depending entirely on you. In this episode, we discuss: ✅ Starting with very little: How Major began his entrepreneurial journey while working three jobs and starting with approximately $1,500. ✅ Finding opportunities in unexpected places: The book "Deals on Wheels" and how it introduced him to mobile home investing. ✅ Taking responsibility: Why blaming the economy, competition, algorithms, or clients doesn't move your business forward. ✅ Focusing on what you control: Putting your attention and energy into the things you can actually influence. ✅ Playing to your strengths: Understanding what you're good at, recognizing your weaknesses, and bringing in help where you need it. ✅ Building systems early: Why documenting your processes makes it easier to delegate and train others. ✅ Delegation and growth: How to stop doing everything yourself and create room to focus on the work that matters most. ✅ Building a business, not just a job: Why freelancers need to think beyond simply trading their time for money. Chapters: 00:00 Introduction: Entrepreneurship, Real Estate, and Freelancing 00:10 Starting With $1,500 While Working Three Jobs 01:36 The Book That Changed Major's Life 02:12 Buying His First Mobile Home Park 04:00 Negotiating Deals and Finding Opportunities 06:00 Building a Real Estate Business From the Ground Up 08:00 Learning Through Experience and Overcoming Challenges 09:00 Why Major Wanted to Share Practical Business Knowledge 11:00 Networking, Collaboration, and Building Relationships 13:00 Turning Knowledge Into Business Opportunities 15:00 Why Entrepreneurs Need to Play to Their Strengths 17:00 Focusing on What You Can Actually Control 19:00 Building Systems and Processes Early 21:00 Why Freelancers Should Think Beyond Selling Their Time 23:00 Delegating and Outsourcing to Grow 25:00 Creating a Business That Doesn't Depend on You 27:00 Avoiding Common Entrepreneurial Mistakes 29:00 Building Confidence Through Experience 31:00 Getting Help and Guidance When Starting Out 33:00 Developing Systems That Can Be Repeated 35:00 Scaling Your Business Without Losing Control 37:00 The Difference Between Building a Job and Building a Business 39:00 Making Your Business More Efficient 41:00 Turning Expertise Into Content and Opportunities 43:00 Why Being Seen and Heard Matters 44:00 Clarifying Your Offer and Serving Your Audience 46:00 Focusing on the Client Instead of Yourself 48:00 Building Trust and Making It Easier to Hire You 50:00 Final Lessons on Growth, Systems, and Entrepreneurship Resources Mentioned Deals on Wheels by Lonnie Scruggs Connect with Major Hillard Website: https://mhestates.com Connect with The Freelance Insider Show Website: https://remoteofficeworld.com Listen to more episodes: https://remoteofficeworld.com/the-freelance-insider-show/ Connect with Al on LinkedIn: https://ca.linkedin.com/in/allan-calder-59066391 If you enjoyed this conversation, subscribe to The Freelance Insider Show for practical conversations about freelancing, finding clients, AI, productivity, and building a sustainable freelance business.

    How to Build a Freelance Business by Thinking Differently (Not Following the Rules)

  2. Oct 19

    Why Skilled Freelancers Stay Broke (And How to Fix It)

    You can be great at what you do and still struggle to get clients if nobody knows who you are. In this episode of The Freelance Insider Show, I’m joined by Christine Blosdale, an expert authority coach with 25 years of media experience, including work with AOL and Microsoft. Christine helps entrepreneurs and business owners become more visible, build trust, and communicate their expertise so the right people understand what they offer. We talk about why talented freelancers often hold themselves back, how to build credibility without feeling like you're bragging, and why being good at your work isn't enough on its own. Christine also shares practical ways to make your expertise more visible, stand out from the competition, and turn that visibility into real business opportunities. In this episode, we discuss: Why Expertise Isn't Enough: Why people need to see and trust you before they're likely to hire you. Overcoming Imposter Syndrome: How fear of judgment and rejection can keep talented freelancers hiding in the background. Building Your Expert Authority: How to identify what makes you different and communicate it clearly. Networking Without the Hard Sell: Why genuine conversations and relationships work better than immediately pitching your services. Charging What You're Worth: Why pricing your services too cheaply can undermine how potential clients perceive your expertise. Getting Comfortable With Visibility: How to put yourself out there without turning yourself into an online personality. Demonstrating Expertise Without Bragging: How to communicate your value in a way that feels authentic and natural. Using AI Without Losing Your Voice: Why AI should enhance your message rather than make you sound like everyone else. Turning Your Content Into More Opportunities: How to repurpose recorded conversations, workshops, and presentations into other forms of content. Making Your Offer Clear: Why potential clients need to understand who you help, what you do, and how you can help them. Using Testimonials to Build Trust: How client feedback can help prospective customers see the value you provide. Choosing the Right Visibility Strategy: Why you should focus on the platforms where your potential clients already spend their time. Chapters: 00:00 Introduction: Visibility, Expertise, and Freelancing 00:29 Christine's Journey From Broadcasting to Expert Authority Coaching 02:45 Why Being Seen and Trusted Matters 03:18 How Podcasting Can Build Long-Term Visibility 04:19 Why Talented People Struggle With Imposter Syndrome 06:13 Using Your Experience to Build Credibility 08:29 Why Freelancers Need Practical, No-Nonsense Advice 09:14 Networking on LinkedIn Without the Hard Sell 11:23 Building Relationships Before Selling 13:15 Turning Conversations Into Opportunities 16:51 Finding a Unique Angle That Helps You Stand Out 17:15 Why Christine Became an Expert Authority Coach 20:03 How to Make Your Expertise More Memorable 21:52 Using Stories to Connect With Your Audience 23:38 Can Expertise Make Imposter Syndrome Worse? 24:01 Overcoming the Fear of Being Seen 26:28 Why Confidence Isn't the Same as Arrogance 27:13 Communicating Your Value With Confidence 28:52 Why Freelancers Shouldn't Compete on Price Alone 29:07 Clarifying Your Offers and Pricing 30:15 Demonstrating the Value of Your Experience 31:29 Why Visibility Can Feel Uncomfortable 32:05 Building Confidence Through Experience 32:43 Getting Testimonials When You're Starting Out 34:14 Self-Promotion vs. Demonstrating Expertise 34:37 Using AI Without Sounding Like Everyone Else 35:17 A Simple Test for Better Messaging 37:03 Becoming More Visible Without Being Everywhere 37:23 Choosing Visibility Strategies You Actually Enjoy 38:09 Turning Recorded Content Into Books and Other Assets 39:24 Why Sharing Your Expertise Builds Authority 40:08 Why Talent Alone Isn't Enough 40:47 Turning Workshops and Videos Into Written Content 41:06 Using Video to Blog to Repurpose Your Content 43:12 Turning Visibility Into Clients and Opportunities 43:30 Why Your Offer Needs to Be Crystal Clear 44:23 Making Your Potential Client the Focus 45:00 Simplifying Your Offers to Help People Decide 45:49 Why Testimonials Help Build Trust 46:15 The Missing Link Between Being Seen and Getting Paid 46:38 Building Trust With Potential Clients 47:18 Making It Easy for Clients to Hire You 48:41 Where to Focus When You Have Limited Time 49:06 Finding the Platforms Where Your Audience Already Is 50:28 Why Desperation Can Push Potential Clients Away 51:04 Get Your Website and Offers Right First 52:19 How to Work With Christine 53:14 Christine's Advice for Freelancers Who Are Hiding 54:00 Final Thoughts on Visibility, Trust, and Getting Paid Connect with Christine Blosdale: Website — https://expertauthoritycoach.com Book a complimentary discovery call — https://chatwithchristineb.com Video to Blog — https://videotoblog.ai Connect with The Freelance Insider Show: Website — https://remoteofficeworld.com Podcast Episodes — https://remoteofficeworld.com/the-freelance-insider-show/ LinkedIn — https://ca.linkedin.com/in/allan-calder-59066391 Subscribe to The Freelance Insider Show for practical conversations about freelancing, finding clients, AI, productivity, and building a sustainable freelance business.

  3. Oct 12

    The #1 Daily Habit of Highly Successful CEOs

    You can be incredibly motivated and still be heading in the wrong direction. When you're constantly chasing the next client, worrying about your pipeline, and trying to keep up with everything, it's easy to sacrifice your well-being in the name of performance. But what if the ability to focus your attention—not simply working harder—is one of the keys to better results? In this episode of The Freelance Insider Show, I sit down with Aaron Hendon, a real estate professional and mindfulness teacher who has spent 30 years helping people perform at higher levels and has coached more than 10,000 people. Known as the Mindful CEO, Aaron shares how mindfulness and meditation can help entrepreneurs and freelancers improve their focus, build stronger client relationships, and create a more sustainable way of working. We explore why mindfulness isn't just about relaxation or personal well-being. It's a practical skill that can help you stay present, listen more effectively, make better business decisions, and stop letting fear dictate your next move. In this episode, we discuss: Mindfulness and Performance: Why your well-being isn't a distraction from success—it's the foundation you perform on.The Hustle Culture Trap: How wearing busyness and exhaustion as badges of honor can undermine your performance.Motivation Isn't Enough: Why inspiration can get you started, but training your attention helps you keep going.The Difference Between Intention and Attention: Why setting goals is one thing, but directing your focus where it needs to be is another.Mindfulness in Sales: How listening without judgment or attachment to an outcome can help build trust and improve client conversations.Training Your Attention Through Meditation: Why meditation isn't about emptying your mind, and how it can help you regain control of your focus.Learning From High Performers: What athletes and other high performers understand about preparation, recovery, and mental performance.Making Mindfulness Practical: Simple ways to bring more awareness into everyday activities—even drinking a cup of coffee.Scarcity Mindset and Client Decisions: How fear about your next paycheck can push you toward draining, unprofitable projects—and how slowing down can help you choose more deliberately.Understanding Imposter Syndrome: Why your brain may be trying to protect you from rejection, and how to recognize that response without letting it run your business.Where to Start When You're Overwhelmed: Aaron's recommendation for freelancers who want to build a healthier, more sustainable business. Timestamps00:00 Introduction: Mindfulness, Performance, and Freelancing 00:24 Aaron's Journey From Business Owner to Mindfulness Teacher 01:42 The Desire to Make Your Life Matter 03:42 Why Well-Being Is the Foundation of Performance 04:42 The Problem With Hustle Culture 05:30 Why Mindfulness Should Be Framed Around Performance 07:22 Intention vs. Attention: Where Does Your Focus Go? 08:21 How Mindful Listening Can Improve Sales 11:55 Why Motivation Alone Doesn't Create Lasting Change 12:22 The Modern Battle for Your Attention 14:00 How Meditation Trains Your Attention 15:20 What Sports Can Teach Us About Mental Performance 18:37 Why High Performers Need to Train Their Minds 20:03 Understanding Your Brain's Pull Toward Distraction 23:37 Learning to Return to the Present Moment 25:33 What Meditation Changes in the Brain 28:20 Bringing Mindfulness Into Everyday Life 30:54 What to Do When Your Mind Wanders During Meditation 32:20 Can Five Minutes of Meditation Make a Difference? 33:18 Meditation, Awareness, and Listening to Your Intuition 34:28 How Scarcity Affects Your Freelance Business 35:38 Why Fear Can Lead You to the Wrong Clients 36:21 How Being Present Helps You Make Better Business Decisions 38:46 Imposter Syndrome: Your Brain's Protection Mechanism 41:16 The First Step for Exhausted and Overwhelmed Freelancers 42:09 Where to Learn Meditation With Aaron 43:14 A Simple Starting Point for Your Mindfulness Practice 43:51 What a Healthier Freelance Business Could Look Like in Six Months Connect with Aaron HendonWebsite: https://aaronhendon.com Connect with The Freelance Insider ShowWebsite: https://remoteofficeworld.com Podcast Episodes: https://remoteofficeworld.com/the-freelance-insider-show/ LinkedIn: https://ca.linkedin.com/in/allan-calder-59066391 Subscribe to The Freelance Insider Show for practical conversations about freelancing, finding clients, AI, productivity, and building a sustainable freelance business.

    The #1 Daily Habit of Highly Successful CEOs

  4. Oct 3

    How to Find Your Freelance Purpose Without Burning Out

    One of the biggest advantages of freelancing is having full control over your work and income. But that control can easily turn into a trap. When your work becomes your entire identity, every client loss feels existential, burnout becomes inevitable, and you end up good at the work but bad at the job of being yourself. In this episode of The Freelance Insider Show, I sit down with Sunnet Bhat, USA Today best-selling author of *Making Sense of Purpose*, EOS Implementer, and former executive who helped scale an organization from 200 to 1,200 people. Today, Sunnet helps individuals and business owners excavate their core purpose, overcome burnout, and decouple their self-worth from their workload. We talk about why tied identity leads to bad business decisions, how to break out of single points of failure in your freelance business, and how practical frameworks can help you regain clarity and momentum. In this episode, we discuss: ■ Good at the Work vs. Bad at Being Yourself: Why high performers often lose their authentic selves inside the roles they play. ■ The Single Point of Failure: Why tying all your happiness, energy, and identity into work creates constant vulnerability. ■ The Feedback Trap: Why 30–40% of feedback becomes counterproductive—and the 3 conditions needed for feedback to actually land. ■ Decoupling Work from Identity: How treating work as just one component of your life frees up space for genuine fulfillment. ■ Making Sense of Purpose: Why purpose isn't something you simply "find" while hungry at the grocery store, but something you excavate from the inside out. ■ The Happy, Proud, Not Yet Satisfied Framework: How to offset natural negativity bias and set goals from a place of positive momentum. ■ Overcoming Burnout: Why burnout is actually a sign of extraordinary strength and how to reframe your work's place in your life. ■ Values Before Everything: Why defining your core values is the essential starting point for every client, pricing, and business decision. 00:00 Introduction & Keeping Freelancing Real 00:31 Sunnet’s 25-Year Journey & The Wake-Up Call 03:56 "Good at the Work, Bad at Being Myself" 07:11 The Common Denominator in Career Patterns 09:09 Why Most Feedback Fails (And How to Fix It) 11:27 Avoiding Single Points of Failure in Identity 15:13 Breaking the Trap of Scarcity Thinking 17:48 Warning Signs Your Work Is Your Whole Identity 19:48 How Identity Distorts Business & Pricing Decisions 22:20 What to Do When You're Successful But Unfulfilled 26:06 Why Purpose Must Be Excavated, Not Discovered 29:22 How Much Time Does Finding Purpose Really Take? 30:51 USA Today Bestseller & *Making Sense of Purpose* 32:00 Looking at Yourself Through Multiple Lenses 36:04 Do These Exercises Actually Work? 38:09 The "Happy, Proud, Not Yet Satisfied" Framework 44:48 When What Makes You Happy Isn't What Makes You Proud 46:04 How to Navigate Burnout & Reframe Your Work 49:48 The First Question to Ask Yourself: Core Values 51:28 Where to Find Sunnet’s Book & Final Thoughts Connect with Suneet Bhatt: ◼ Website — https://MakingSenseOfPurpose.com The Freelance Insider Show: ◼ Website — https://remoteofficeworld.com ◼ Podcast Episodes — https://remoteofficeworld.com/the-freelance-insider-show/ ◼ LinkedIn — https://ca.linkedin.com/in/allan-calder-59066391 Subscribe to The Freelance Insider Show for practical conversations about freelancing, finding clients, AI, productivity, and building a sustainable freelance business.

    How to Find Your Freelance Purpose Without Burning Out

  5. Sep 24

    Removing Yourself as the Bottleneck - What That Means for Freelancers

    One of the biggest advantages of freelancing is that you don't need a big team to build a business. But that can also become one of your biggest problems. When you're the business, everything depends on you. More clients can mean more money, but they can also mean more work, more admin, more emails—and ultimately less freedom. In this episode of The Freelance Insider Show, I sit down with Jordan Solander, an entrepreneur and business coach who has been building businesses since he was 13, starting with a snowplow business and eventually building and exiting an eight-figure company. Today, Jordan helps business owners identify and eliminate the bottlenecks that keep their businesses dependent on them. We talk about why doing everything yourself can actually prevent your business from growing, how freelancers can create leverage without hiring a large team, and how systems, virtual assistants, contractors, automation, and AI can help you get your time back. In this episode, we discuss: ■ The Bottleneck Problem: Why the skills that make you successful in the early stages of a business can eventually become the very things that hold it back. ■ "Nobody Can Do It Like I Can": Why entrepreneurs struggle to delegate—and why someone doesn't need to do something exactly your way for it to be valuable. ■ Systems Before Employees: Why freelancers don't need a staff of 30 people to start creating leverage in their business. ■ The Leverage Stack: How virtual assistants, contractors, automation, and AI can take repetitive work off your plate without requiring a traditional team. ■ The Ego Trap: Why doing everything yourself isn't always hustle or work ethic—and can sometimes be ego disguised as productivity. ■ Delegation vs. Abdication: How to give someone an outcome, guardrails, and the authority to make decisions without simply handing over the keys to your business. ■ The Pick One Thing and Remove Yourself Sprint: A simple way to start identifying the work you shouldn't be doing anymore. ■ Building Institutional Knowledge: How documenting repetitive processes can turn the knowledge in your head into systems that allow your business to operate without you. ■ The 30-Day Test: Jordan's ultimate test for determining whether you've actually removed yourself as a bottleneck. 00:00 The Freelancer's Bottleneck Problem 01:11 Jordan Solander's Entrepreneurial Journey 01:16 Starting a Business at 13 02:36 How Jordan Became the Bottleneck 04:20 You Didn't Build a Business—You Built Yourself a Job 04:38 Systems and Leverage for Freelancers 06:09 Why Doing Everything Yourself Isn't Always Hustle 06:31 The Ego and Control Problem 07:55 Delegation vs. Abdication 09:20 What Should You Actually Delegate? 11:10 Building Leverage Without Employees 13:00 How to Start Working With a VA 15:00 The Right Way to Delegate 17:00 Why Smart People Leave When You Micromanage 19:00 Finding the Bottlenecks in Your Business 21:00 The Pick One Thing and Remove Yourself Sprint 23:20 Building Institutional Knowledge 26:00 The 30-Day Test 32:00 How to Safely Delegate and Protect Your Business 34:00 Removing One Thing at a Time 44:00 Turning Freed-Up Time Into Revenue 45:46 Jordan's Business Coaching and AI Agency 46:39 The Ultimate Test: Can You Walk Away for 30 Days? 47:24 Final Thoughts Connect with Jordan Solander: ◼ Business coaching — https://JordanSolander.com ◼ AI agency — https://solander.ai The Freelance Insider Show: ◼ Website — https://remoteofficeworld.com ◼ Podcast Episodes — https://remoteofficeworld.com/the-freelance-insider-show/ ◼ LinkedIn - https://ca.linkedin.com/in/allan-calder-59066391 Subscribe to The Freelance Insider Show for practical conversations about freelancing, finding clients, AI, productivity, and building a sustainable freelance business.

    Removing Yourself as the Bottleneck - What That Means for Freelancers

  6. Sep 12

    The Freelance Advice That No Longer Works in 2026

    The freelance playbook has changed. If you're still relying on generic proposals, polished portfolios, and Upwork to land clients in 2026, you may be competing with thousands of freelancers using exactly the same strategy. In this episode of **The Freelance Insider Show**, I break down why so many freelancers are struggling to get hired—and what actually needs to change if you want to attract better freelance clients in 2026. AI has made it easier than ever to create portfolios, write proposals, and compete on freelance platforms. That means the things that used to make you stand out may now be nothing more than the minimum expectation. I'll walk you through the four biggest mistakes keeping freelancers stuck, and then show you the 2026 freelance client-acquisition strategy I believe makes far more sense. What you'll learn: • Why static portfolios aren't enough to differentiate you anymore • Why selling your services instead of the outcome is a losing strategy • Why asking a potential client for a 30-minute call creates unnecessary friction • How to address the anxiety clients have about hiring remote freelancers • The Micro-Value Pitch Formula for getting conversations started • How a "predictability clause" can make you a safer choice for clients • How to use LinkedIn to find potential clients instead of fighting for attention on Upwork • Why your first freelance projects should be about building social proof—not getting rich • How to use testimonials to eventually move toward better clients and higher rates The good news? "Freelancing isn't dead." But the old, lazy approach of sending dozens of generic proposals and hoping someone bites is becoming increasingly difficult to sustain. The freelancers who can identify real problems, demonstrate value before asking for anything, reduce client risk, and focus on outcomes instead of commodities will have a much better chance of standing out. If you're a new or struggling freelancer trying to figure out how to get freelance clients in 2026, this episode is for you. 👉 **Subscribe to The Freelance Insider Show** for more practical strategies on freelancing, finding clients, AI, productivity, and building a sustainable freelance business.

  7. Aug 21

    Why 1 Freelance Retainer Client Is DANGEROUS

    Having a high paying retainer client feels like the ultimate freelance dream - until it becomes your single point if failure. In this episode, I share how relying on just one main retainer client backfired when they suddenly ghosted me, taking $2000/week off my bottom line overnight. Learn why single client dependency is a dangerous trap, how to spot the warning signs in your freelance business, and the exact steps to build a diversified client portfolio that keeps your income secure. 🔔Subscribe for weekly freelance strategies and practical business advice. RESOURCES & LINKS 🌐website: https://remoteofficeworld.com/the-freelance-insider-show/ 🎙️ The Freelance Insider Show 🎙️ Subscribe so you never miss an episode ➡️

    Why 1 Freelance Retainer Client Is DANGEROUS

  8. Jun 11

    Freelance Imposter Syndrome and The Creator Success Staircase

    I spent years blaming everything except the mirror. In this episode of The Freelance Insider Show, I share my origin story — the one mindset mistake I made at the start of my freelance career that cost me 10 years of growth, and the simple shift (the Creator Success Staircase) that changes everything. 🔑 In this episode: ✔️ The Creator Success Staircase framework explained ✔️ Why imposter syndrome is the real barrier — not circumstance ✔️ Why platforms like Upwork keep you stuck ✔️ How cold pitching beats competing against 50 proposals ✔️ The one thing you need to commit to starting today 📌 Highlights:  – The Creator Success Staircase  – My 2012 story: nearly losing the house  – The early 2000s web design business mistake  – The mindset shift: stop waiting for permission  – Upwork vs. cold pitching strategy  – How to unlock the gate and keep going 🎙️ The Freelance Insider Show  🎙️ Subscribe so you never miss an episode ➡️ https://remoteofficeworld.com/the-freelance-insider-show/ ➡️ Other Resources & Links: ✔️ Freelance Reset Checklist (free): https://remoteofficeworld.com/ ✔️Al’s LinkedIn: https://www.linkedin.com/in/allan-calder-59066391/

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About

The Freelance Insider Show gives you a real-world look at what it takes to build and grow a successful freelance business. Whether you're just starting out or leveling up, each weekly episode delivers practical tips, strategies, and no-fluff advice you can actually use — from landing clients and setting your rates to managing burnout and staying motivated. 🎯 Ready to hit reset and build a freelance business that works for you? Grab your free Freelance Reset Checklist at https://alcalder.eo.page/hq52z and start strong. Let’s get started!

Information

  • Creator
    Al Calder
  • Years Active
    2025 - 2026
  • Episodes
    36
  • Rating
    Explicit
  • Copyright
    © All rights reserved.
  • Show Website
    The Freelance Insider Show