Side Hustle School

Side Hustle School

By Chris Guillebeau
Download on the App Store

Side Hustle School episodes

  • Dachshund-Loving Duo Designs Doxie Apparel
    What It’s About
    A couple taps into doxie fandom to build a six-figure apparel side hustle.

    Notes from Chris
    Episode 3291

    In today’s story…

    It’s all about dachshunds! And not just the dogs, but the designs. Woof.

    Listen to today’s episode to learn more…

     

     

    SEE ALSO:

    • Catholic Designer Creates Stylish Apparel Line: What shall it profit a man to gain the whole world but not sell any t-shirts? This designer cast his bread upon the waters and ended up with a profitable fashion line.
    • Seattle Couple Creates New “Income LiveStream”: When a married couple runs into logistical problems at their wedding, it leads to an innovative service that other engaged couples need during the pandemic.
    • Role-Playing Pastor Rolls The Dice On $2800/Month Hustle: Listener success story! This Presbyterian minister turns to his lifelong interest in role-playing games to set up a sustainable second income source.
    • Inspiration is good; inspiration combined with action is better. Now get back to work!

      Yours in the revolution,

      <img class="alignnone wp-image-1825" src="https://sidehustleschool.com/wp-content/uploads/2017/04/CG-Sig-Newsletter-300x140.png" alt="cg-sig-newsletter" width="176" height="82" srcset="https://sidehustleschool.com/wp-content/uploads/2017/04/CG-Sig-Newsletter-300x140.png 300w, https://sidehustleschool.com/wp-content/uploads/2017/04/CG-Sig-Newsletter.png 450w" sizes="(max-width: 176px) 100vw, 176px">

      Resources
      GET $625 IN FREE TRAVEL

      Earn 50,000 travel rewards points (enough for 2 round-trip plane tickets or $625 in travel credit). You'll also earn 2x points on all travel and dining spend, with zero foreign transaction fees.

      I use this card every day all over the world! ✈️

      Learn More

      CREATE YOUR ONLINE STORE

      Create your online store with Shopify using an exclusive discount for Side Hustle School listeners. For a limited time, get a free 21-day trial and a 10% discount for a whole year.

      Many Side Hustle School listeners are building sites using Shopify's easy-to-learn platform. Try it free today!

      Learn More

      Sponsors & Gratitude
      Learn More With Skillshare!

      Supporting the sponsors keeps the show free. Today’s episode of Side Hustle School is brought to you by Skillshare. 📷

      Skillshare is giving Side Hustle School listeners 2 months of unlimited access—for $0.99! Join the 2 million students learning everything from street photography to SEO on Skillshare today!

      Get Started Here!

      Like the Show? Leave a Rating!

      Side Hustle School is for you! If you’re enjoying it, please take a quick moment to leave a rating or write a quick review. It's really easy and it makes a difference! ✅

      It also makes a huge difference when you tell your friends about the show. Remember, it's 100% free and listener-supported.


      Here's How

      Keep in Touch
      <img class="aligncenter wp-image-1272 size-full" src="https://sidehustleschool.com/wp-content/uploads/2017/03/ChrisGuillebeauSideHustleSchoolFull-1.jpg" width="1076" height="251">
      There’s a new story every single day on Side Hustle School. Episodes are produced to be short and to the point—I know you’re busy. Be sure you subscribe to get instant notification of the day’s broadcast!

      Follow

      Facebook,Instagram,Twitter

      Email

      Say Hi

      From your favorite airport

      To infinity and beyond,

      Chris Guillebeau
      9 min
    • Q&A: “What if you don’t want to use social media?”
      What It’s About
      Do you really need social media to reach the right buyers?

      Notes from Chris
      Episode 3290

      This listener makes motion videos and backgrounds for churches, but he dislikes social media (#notafan). Should he just get over his resistance, or can he succeed without frequent posting?

      “My Side hustle is making motion videos and backgrounds for churches to use on their Sunday morning services. My question is, is it possible to build a thriving side hustle or business without harnessing social media?Hashtag: #notafan. Currently, the videos I make our uploaded to one site where they take care of all the marketing and branding and I get paid a commission on every video that’s downloaded.

      I have recently started my own web site so that I can retain full commission on everything that sells. But I know I need to get the word out there to my target audience. So what would you recommend on reaching those people without using Facebook, Twitter, Instagram and all that stuff?”

      Listen to today’s episode to learn more…

       

       

      SEE ALSO:

      • Catholic Designer Creates Stylish Apparel Line: What shall it profit a man to gain the whole world but not sell any t-shirts? This designer cast his bread upon the waters and ended up with a profitable fashion line.
      • Seattle Couple Creates New “Income LiveStream”: When a married couple runs into logistical problems at their wedding, it leads to an innovative service that other engaged couples need during the pandemic.
      • Role-Playing Pastor Rolls The Dice On $2800/Month Hustle: Listener success story! This Presbyterian minister turns to his lifelong interest in role-playing games to set up a sustainable second income source.
      • Inspiration is good; inspiration combined with action is better. Now get back to work!

        Yours in the revolution,

        <img class="alignnone wp-image-1825" src="https://sidehustleschool.com/wp-content/uploads/2017/04/CG-Sig-Newsletter-300x140.png" alt="cg-sig-newsletter" width="176" height="82" srcset="https://sidehustleschool.com/wp-content/uploads/2017/04/CG-Sig-Newsletter-300x140.png 300w, https://sidehustleschool.com/wp-content/uploads/2017/04/CG-Sig-Newsletter.png 450w" sizes="(max-width: 176px) 100vw, 176px">

        Resources
        GET $625 IN FREE TRAVEL

        Earn 50,000 travel rewards points (enough for 2 round-trip plane tickets or $625 in travel credit). You'll also earn 2x points on all travel and dining spend, with zero foreign transaction fees.

        I use this card every day all over the world! ✈️

        Learn More

        CREATE YOUR ONLINE STORE

        Create your online store with Shopify using an exclusive discount for Side Hustle School listeners. For a limited time, get a free 21-day trial and a 10% discount for a whole year.

        Many Side Hustle School listeners are building sites using Shopify's easy-to-learn platform. Try it free today!

        Learn More

        Sponsors & Gratitude
        Learn More With Skillshare!

        Supporting the sponsors keeps the show free. Today’s episode of Side Hustle School is brought to you by Skillshare. 📷

        Skillshare is giving Side Hustle School listeners 2 months of unlimited access—for $0.99! Join the 2 million students learning everything from street photography to SEO on Skillshare today!

        Get Started Here!

        Like the Show? Leave a Rating!

        Side Hustle School is for you! If you’re enjoying it, please take a quick moment to leave a rating or write a quick review. It's really easy and it makes a difference! ✅

        It also makes a huge difference when you tell your friends about the show. Remember, it's 100% free and listener-supported.


        Here's How

        Keep in Touch
        <img class="aligncenter wp-image-1272 size-full" src="https://sidehustleschool.com/wp-content/uploads/2017/03/ChrisGuillebeauSideHustleSchoolFull-1.jpg" width="1076" height="251">
        There’s a new story every single day on Side Hustle School. Episodes are produced to be short and to the point—I know you’re busy. Be sure you subscribe to get instant notification of the day’s broadcast!

        Follow

        Facebook,Instagram,Twitter

        Email

        Say Hi

        From your favorite airport

        To infinity and beyond,

        Chris Guillebeau
        7 min
      • Rent the Chicken! An Egg-Cellent Idea Clucks Into Cash
        What It’s About
        A Pennsylvania couple turns backyard chickens into a rentable, scalable side hustle.

        Notes from Chris
        Episode 3289

        In today’s story…

        Have you ever wanted to keep a chicken as a pet, but weren’t sure you were up for a lifetime commitment? Today’s featured story has just the solution for you: no need to buy chickens when you can rent.

        Listen to today’s episode to learn more…

         

         

        SEE ALSO:

        • Catholic Designer Creates Stylish Apparel Line: What shall it profit a man to gain the whole world but not sell any t-shirts? This designer cast his bread upon the waters and ended up with a profitable fashion line.
        • Seattle Couple Creates New “Income LiveStream”: When a married couple runs into logistical problems at their wedding, it leads to an innovative service that other engaged couples need during the pandemic.
        • Role-Playing Pastor Rolls The Dice On $2800/Month Hustle: Listener success story! This Presbyterian minister turns to his lifelong interest in role-playing games to set up a sustainable second income source.
        • Inspiration is good; inspiration combined with action is better. Now get back to work!

          Yours in the revolution,

          <img class="alignnone wp-image-1825" src="https://sidehustleschool.com/wp-content/uploads/2017/04/CG-Sig-Newsletter-300x140.png" alt="cg-sig-newsletter" width="176" height="82" srcset="https://sidehustleschool.com/wp-content/uploads/2017/04/CG-Sig-Newsletter-300x140.png 300w, https://sidehustleschool.com/wp-content/uploads/2017/04/CG-Sig-Newsletter.png 450w" sizes="(max-width: 176px) 100vw, 176px">

          Resources
          GET $625 IN FREE TRAVEL

          Earn 50,000 travel rewards points (enough for 2 round-trip plane tickets or $625 in travel credit). You'll also earn 2x points on all travel and dining spend, with zero foreign transaction fees.

          I use this card every day all over the world! ✈️

          Learn More

          CREATE YOUR ONLINE STORE

          Create your online store with Shopify using an exclusive discount for Side Hustle School listeners. For a limited time, get a free 21-day trial and a 10% discount for a whole year.

          Many Side Hustle School listeners are building sites using Shopify's easy-to-learn platform. Try it free today!

          Learn More

          Sponsors & Gratitude
          Learn More With Skillshare!

          Supporting the sponsors keeps the show free. Today’s episode of Side Hustle School is brought to you by Skillshare. 📷

          Skillshare is giving Side Hustle School listeners 2 months of unlimited access—for $0.99! Join the 2 million students learning everything from street photography to SEO on Skillshare today!

          Get Started Here!

          Like the Show? Leave a Rating!

          Side Hustle School is for you! If you’re enjoying it, please take a quick moment to leave a rating or write a quick review. It's really easy and it makes a difference! ✅

          It also makes a huge difference when you tell your friends about the show. Remember, it's 100% free and listener-supported.


          Here's How

          Keep in Touch
          <img class="aligncenter wp-image-1272 size-full" src="https://sidehustleschool.com/wp-content/uploads/2017/03/ChrisGuillebeauSideHustleSchoolFull-1.jpg" width="1076" height="251">
          There’s a new story every single day on Side Hustle School. Episodes are produced to be short and to the point—I know you’re busy. Be sure you subscribe to get instant notification of the day’s broadcast!

          Follow

          Facebook,Instagram,Twitter

          Email

          Say Hi

          From your favorite airport

          To infinity and beyond,

          Chris Guillebeau
          6 min
        • Military-Themed Teddy Bears Help Kids Hibernate
          What It’s About
          A copywriter turns bedtime fears into a six-figure teddy bear business.

          Notes from Chris
          Episode 3287

          In today’s story…

          ..an ad executive and former copywriter for the US Marine Corps becomes a DIY teddy bear supplier, offering what he calls a “military-grade sleep system for children.”

          Listen to today’s episode to learn more…

           

           

          SEE ALSO:

          • Catholic Designer Creates Stylish Apparel Line: What shall it profit a man to gain the whole world but not sell any t-shirts? This designer cast his bread upon the waters and ended up with a profitable fashion line.
          • Seattle Couple Creates New “Income LiveStream”: When a married couple runs into logistical problems at their wedding, it leads to an innovative service that other engaged couples need during the pandemic.
          • Role-Playing Pastor Rolls The Dice On $2800/Month Hustle: Listener success story! This Presbyterian minister turns to his lifelong interest in role-playing games to set up a sustainable second income source.
          • Inspiration is good; inspiration combined with action is better. Now get back to work!

            Yours in the revolution,

            <img class="alignnone wp-image-1825" src="https://sidehustleschool.com/wp-content/uploads/2017/04/CG-Sig-Newsletter-300x140.png" alt="cg-sig-newsletter" width="176" height="82" srcset="https://sidehustleschool.com/wp-content/uploads/2017/04/CG-Sig-Newsletter-300x140.png 300w, https://sidehustleschool.com/wp-content/uploads/2017/04/CG-Sig-Newsletter.png 450w" sizes="(max-width: 176px) 100vw, 176px">

            Resources
            GET $625 IN FREE TRAVEL

            Earn 50,000 travel rewards points (enough for 2 round-trip plane tickets or $625 in travel credit). You'll also earn 2x points on all travel and dining spend, with zero foreign transaction fees.

            I use this card every day all over the world! ✈️

            Learn More

            CREATE YOUR ONLINE STORE

            Create your online store with Shopify using an exclusive discount for Side Hustle School listeners. For a limited time, get a free 21-day trial and a 10% discount for a whole year.

            Many Side Hustle School listeners are building sites using Shopify's easy-to-learn platform. Try it free today!

            Learn More

            Sponsors & Gratitude
            Learn More With Skillshare!

            Supporting the sponsors keeps the show free. Today’s episode of Side Hustle School is brought to you by Skillshare. 📷

            Skillshare is giving Side Hustle School listeners 2 months of unlimited access—for $0.99! Join the 2 million students learning everything from street photography to SEO on Skillshare today!

            Get Started Here!

            Like the Show? Leave a Rating!

            Side Hustle School is for you! If you’re enjoying it, please take a quick moment to leave a rating or write a quick review. It's really easy and it makes a difference! ✅

            It also makes a huge difference when you tell your friends about the show. Remember, it's 100% free and listener-supported.


            Here's How

            Keep in Touch
            <img class="aligncenter wp-image-1272 size-full" src="https://sidehustleschool.com/wp-content/uploads/2017/03/ChrisGuillebeauSideHustleSchoolFull-1.jpg" width="1076" height="251">
            There’s a new story every single day on Side Hustle School. Episodes are produced to be short and to the point—I know you’re busy. Be sure you subscribe to get instant notification of the day’s broadcast!

            Follow

            Facebook,Instagram,Twitter

            Email

            Say Hi

            From your favorite airport

            To infinity and beyond,

            Chris Guillebeau
            7 min
          • Q&A: “After 8 years of daily episodes, what’s next?”
            What It’s About
            Is the journey finally over? ABSOLUTELY NOT!

            Notes from Chris
            Episode 3286

            Wrapping up a year is a good moment to ask, “What did we learn, and what should we do differently?” The show exists to help real people earn real money, so the plan is simple: keep what works, fix what doesn’t, and try a couple of bold tests. I’ll share where the podcast is headed, the kinds of episodes you’ll hear more of, and a few projects I’m building alongside the show.

            “Hi Chris, longtime listener here. As the year winds down, I’m curious about the future of Side Hustle School. What kinds of stories or experiments are you planning next? And beyond the podcast, what else will you be working on—books, workshops, community projects? I love the show and would love a peek behind the scenes at what’s staying, what might evolve, and how listeners like me can be part of it.”

            Listen to today’s episode to learn more…

             

             

            SEE ALSO:

            • Catholic Designer Creates Stylish Apparel Line: What shall it profit a man to gain the whole world but not sell any t-shirts? This designer cast his bread upon the waters and ended up with a profitable fashion line.
            • Seattle Couple Creates New “Income LiveStream”: When a married couple runs into logistical problems at their wedding, it leads to an innovative service that other engaged couples need during the pandemic.
            • Role-Playing Pastor Rolls The Dice On $2800/Month Hustle: Listener success story! This Presbyterian minister turns to his lifelong interest in role-playing games to set up a sustainable second income source.
            • Inspiration is good; inspiration combined with action is better. Now get back to work!

              Yours in the revolution,

              <img class="alignnone wp-image-1825" src="https://sidehustleschool.com/wp-content/uploads/2017/04/CG-Sig-Newsletter-300x140.png" alt="cg-sig-newsletter" width="176" height="82" srcset="https://sidehustleschool.com/wp-content/uploads/2017/04/CG-Sig-Newsletter-300x140.png 300w, https://sidehustleschool.com/wp-content/uploads/2017/04/CG-Sig-Newsletter.png 450w" sizes="(max-width: 176px) 100vw, 176px">

              Resources
              GET $625 IN FREE TRAVEL

              Earn 50,000 travel rewards points (enough for 2 round-trip plane tickets or $625 in travel credit). You'll also earn 2x points on all travel and dining spend, with zero foreign transaction fees.

              I use this card every day all over the world! ✈️

              Learn More

              CREATE YOUR ONLINE STORE

              Create your online store with Shopify using an exclusive discount for Side Hustle School listeners. For a limited time, get a free 21-day trial and a 10% discount for a whole year.

              Many Side Hustle School listeners are building sites using Shopify's easy-to-learn platform. Try it free today!

              Learn More

              Sponsors & Gratitude
              Learn More With Skillshare!

              Supporting the sponsors keeps the show free. Today’s episode of Side Hustle School is brought to you by Skillshare. 📷

              Skillshare is giving Side Hustle School listeners 2 months of unlimited access—for $0.99! Join the 2 million students learning everything from street photography to SEO on Skillshare today!

              Get Started Here!

              Like the Show? Leave a Rating!

              Side Hustle School is for you! If you’re enjoying it, please take a quick moment to leave a rating or write a quick review. It's really easy and it makes a difference! ✅

              It also makes a huge difference when you tell your friends about the show. Remember, it's 100% free and listener-supported.


              Here's How

              Keep in Touch
              <img class="aligncenter wp-image-1272 size-full" src="https://sidehustleschool.com/wp-content/uploads/2017/03/ChrisGuillebeauSideHustleSchoolFull-1.jpg" width="1076" height="251">
              There’s a new story every single day on Side Hustle School. Episodes are produced to be short and to the point—I know you’re busy. Be sure you subscribe to get instant notification of the day’s broadcast!

              Follow

              Facebook,Instagram,Twitter

              Email

              Say Hi

              From your favorite airport

              To infinity and beyond,

              Chris Guillebeau
              6 min
            • First $1,000: A Discord Server That Pays the Rent
              What It’s About
              A niche Discord community turns collaboration into $1,800 a month.

              Notes from Chris
              Episode 3285

              Today’s episode is part of a feature we call ‘Your First $1,000.’ As you might surmise from the title, this is all about how someone made their first $1,000.

              How did they get to that point? Not their first $100,000—that’s cool, but it would probably be a long story.

              But what about their first $1,000—how did they make that happen, what did it feel like, and what did they learn?

              Let’s hear today’s story. I’ll be back at the end to wrap us up. 

               

               

              SEE ALSO:

              • Military Spouse Starts Subscription Box Mission:When an HR Director’s husband is away on military deployment, she uses the alone time to march toward a subscription box.
              • Think Inside the Subscription Box:Looking for more community, a North Carolina web agency owner starts a subscription box for female entrepreneurs. It’s supposed to be a referral tool for her agency, but it ends up becoming a full-time business of its own.
              • Nature-Loving Neighbors Create Kids Subscription Box: When two couples can’t figure out how to get their kids outdoors and away from electronics in the winter, a personal challenge blossoms into an unbeLEAFable side hustle.
              • Inspiration is good; inspiration combined with action is better. Now get back to work!

                Yours in the revolution,

                <img class="alignnone wp-image-1825" src="https://sidehustleschool.com/wp-content/uploads/2017/04/CG-Sig-Newsletter-300x140.png" alt="cg-sig-newsletter" width="176" height="82" srcset="https://sidehustleschool.com/wp-content/uploads/2017/04/CG-Sig-Newsletter-300x140.png 300w, https://sidehustleschool.com/wp-content/uploads/2017/04/CG-Sig-Newsletter.png 450w" sizes="(max-width: 176px) 100vw, 176px">

                Resources
                WEB HOSTING @ $2.49/MONTH

                Want to build any kind of website for your hustle? If so, you'll need somewhere to host it! This is the reliable company I've used for many websites. It's cheap, flexible, and offers support 24-7.

                Get your own hosting plan for just $2.49 a month!

                Learn More

                GET $625 IN FREE TRAVEL

                Earn 50,000 travel rewards points (enough for 2 round-trip plane tickets or $625 in travel credit). You'll also earn 2x points on all travel and dining spend, with zero foreign transaction fees.

                I use this card every day all over the world! ✈️

                Learn More

                Sponsors & Gratitude
                Don't Do Business Without It

                Side Hustle School is brought to you by American Express.

                No matter what you do in business, from working nine-to-five to working five-to-nine, it’s easier when you don’t go it alone. Get the powerful backing of American Express—don't do business without it! 💳

                Visit American Express

                Like the Show? Leave a Rating!

                Side Hustle School is for you! If you’re enjoying it, please take a quick moment to leave a rating or write a quick review. It's really easy and it makes a difference! ✅

                It also makes a huge difference when you tell your friends about the show. Remember, it's 100% free and listener-supported.

                Here's How

                Keep in Touch
                <img class="aligncenter wp-image-1272 size-full" src="https://sidehustleschool.com/wp-content/uploads/2017/03/ChrisGuillebeauSideHustleSchoolFull-1.jpg" width="1076" height="251">
                There’s a new story every single day on Side Hustle School. Episodes are produced to be short and to the point—I know you’re busy. Be sure you subscribe to get instant notification of the day’s broadcast!

                Follow

                Facebook,Instagram,Twitter

                Email

                Say Hi

                From your favorite airport

                To infinity and beyond,

                Chris Guillebeau
                7 min
              • Weekend Workshop: From Wedding Dresses to State Legislature
                What It’s About
                From bridal design to public office, one founder bets on independence.

                Notes from Chris
                Episode 3284

                It’s Weekend Workshop, and it’s new!

                Listen to today’s episode to learn more…

                 

                 

                SEE ALSO:

                • Catholic Designer Creates Stylish Apparel Line: What shall it profit a man to gain the whole world but not sell any t-shirts? This designer cast his bread upon the waters and ended up with a profitable fashion line.
                • Seattle Couple Creates New “Income LiveStream”: When a married couple runs into logistical problems at their wedding, it leads to an innovative service that other engaged couples need during the pandemic.
                • Role-Playing Pastor Rolls The Dice On $2800/Month Hustle: Listener success story! This Presbyterian minister turns to his lifelong interest in role-playing games to set up a sustainable second income source.
                • Inspiration is good; inspiration combined with action is better. Now get back to work!

                  Yours in the revolution,

                  <img class="alignnone wp-image-1825" src="https://sidehustleschool.com/wp-content/uploads/2017/04/CG-Sig-Newsletter-300x140.png" alt="cg-sig-newsletter" width="176" height="82" srcset="https://sidehustleschool.com/wp-content/uploads/2017/04/CG-Sig-Newsletter-300x140.png 300w, https://sidehustleschool.com/wp-content/uploads/2017/04/CG-Sig-Newsletter.png 450w" sizes="(max-width: 176px) 100vw, 176px">

                  Resources
                  GET $625 IN FREE TRAVEL

                  Earn 50,000 travel rewards points (enough for 2 round-trip plane tickets or $625 in travel credit). You'll also earn 2x points on all travel and dining spend, with zero foreign transaction fees.

                  I use this card every day all over the world! ✈️

                  Learn More

                  CREATE YOUR ONLINE STORE

                  Create your online store with Shopify using an exclusive discount for Side Hustle School listeners. For a limited time, get a free 21-day trial and a 10% discount for a whole year.

                  Many Side Hustle School listeners are building sites using Shopify's easy-to-learn platform. Try it free today!

                  Learn More

                  Sponsors & Gratitude
                  Learn More With Skillshare!

                  Supporting the sponsors keeps the show free. Today’s episode of Side Hustle School is brought to you by Skillshare. 📷

                  Skillshare is giving Side Hustle School listeners 2 months of unlimited access—for $0.99! Join the 2 million students learning everything from street photography to SEO on Skillshare today!

                  Get Started Here!

                  Like the Show? Leave a Rating!

                  Side Hustle School is for you! If you’re enjoying it, please take a quick moment to leave a rating or write a quick review. It's really easy and it makes a difference! ✅

                  It also makes a huge difference when you tell your friends about the show. Remember, it's 100% free and listener-supported.


                  Here's How

                  Keep in Touch
                  <img class="aligncenter wp-image-1272 size-full" src="https://sidehustleschool.com/wp-content/uploads/2017/03/ChrisGuillebeauSideHustleSchoolFull-1.jpg" width="1076" height="251">
                  There’s a new story every single day on Side Hustle School. Episodes are produced to be short and to the point—I know you’re busy. Be sure you subscribe to get instant notification of the day’s broadcast!

                  Follow

                  Facebook,Instagram,Twitter

                  Email

                  Say Hi

                  From your favorite airport

                  To infinity and beyond,

                  Chris Guillebeau
                  8 min
                • Q&A: “How can I keep from negotiating against myself?”
                  What It’s About
                  Can a simple pricing structure stop premature discounts?

                  Notes from Chris
                  Episode 3283

                  Self-discounting usually isn’t about money—it’s about nerves. The fix is less willpower and more structure: a set price sheet, a one-sentence response, and a two-second pause you practice until silence feels normal. Let’s give the photographer a quick system she can deploy on the very next inquiry.

                  “Whenever someone inquires, I panic and say things like ‘My rate is $600, but I can do $500 if that helps.’ They hadn’t even objected yet. It’s costing me revenue and reinforcing insecurity. How do I break this habit of negotiating against myself? Are there scripts, confidence exercises, or pricing structures that prevent me from rushing to a discount out of fear?”

                  Listen to today’s episode to learn more…

                   

                   

                  SEE ALSO:

                  • Catholic Designer Creates Stylish Apparel Line: What shall it profit a man to gain the whole world but not sell any t-shirts? This designer cast his bread upon the waters and ended up with a profitable fashion line.
                  • Seattle Couple Creates New “Income LiveStream”: When a married couple runs into logistical problems at their wedding, it leads to an innovative service that other engaged couples need during the pandemic.
                  • Role-Playing Pastor Rolls The Dice On $2800/Month Hustle: Listener success story! This Presbyterian minister turns to his lifelong interest in role-playing games to set up a sustainable second income source.
                  • Inspiration is good; inspiration combined with action is better. Now get back to work!

                    Yours in the revolution,

                    <img class="alignnone wp-image-1825" src="https://sidehustleschool.com/wp-content/uploads/2017/04/CG-Sig-Newsletter-300x140.png" alt="cg-sig-newsletter" width="176" height="82" srcset="https://sidehustleschool.com/wp-content/uploads/2017/04/CG-Sig-Newsletter-300x140.png 300w, https://sidehustleschool.com/wp-content/uploads/2017/04/CG-Sig-Newsletter.png 450w" sizes="(max-width: 176px) 100vw, 176px">

                    Resources
                    GET $625 IN FREE TRAVEL

                    Earn 50,000 travel rewards points (enough for 2 round-trip plane tickets or $625 in travel credit). You'll also earn 2x points on all travel and dining spend, with zero foreign transaction fees.

                    I use this card every day all over the world! ✈️

                    Learn More

                    CREATE YOUR ONLINE STORE

                    Create your online store with Shopify using an exclusive discount for Side Hustle School listeners. For a limited time, get a free 21-day trial and a 10% discount for a whole year.

                    Many Side Hustle School listeners are building sites using Shopify's easy-to-learn platform. Try it free today!

                    Learn More

                    Sponsors & Gratitude
                    Learn More With Skillshare!

                    Supporting the sponsors keeps the show free. Today’s episode of Side Hustle School is brought to you by Skillshare. 📷

                    Skillshare is giving Side Hustle School listeners 2 months of unlimited access—for $0.99! Join the 2 million students learning everything from street photography to SEO on Skillshare today!

                    Get Started Here!

                    Like the Show? Leave a Rating!

                    Side Hustle School is for you! If you’re enjoying it, please take a quick moment to leave a rating or write a quick review. It's really easy and it makes a difference! ✅

                    It also makes a huge difference when you tell your friends about the show. Remember, it's 100% free and listener-supported.


                    Here's How

                    Keep in Touch
                    <img class="aligncenter wp-image-1272 size-full" src="https://sidehustleschool.com/wp-content/uploads/2017/03/ChrisGuillebeauSideHustleSchoolFull-1.jpg" width="1076" height="251">
                    There’s a new story every single day on Side Hustle School. Episodes are produced to be short and to the point—I know you’re busy. Be sure you subscribe to get instant notification of the day’s broadcast!

                    Follow

                    Facebook,Instagram,Twitter

                    Email

                    Say Hi

                    From your favorite airport

                    To infinity and beyond,

                    Chris Guillebeau
                    6 min
                  • Q&A: “How do I raise rates without losing clients?”
                    What It’s About
                    How do you test higher prices without risking your best clients?

                    Notes from Chris
                    Episode 3282

                    Price hikes feel risky, yet flat rates quietly erode profit and energy. Most long-term clients won’t leave if the new fee still feels fair and the notice is clear. The goal isn’t squeezing every dollar; it’s matching price to value so you can keep serving well—and sustainably.

                    “I run a small bookkeeping side hustle. I’ve charged the same monthly retainer since 2022 because I’m terrified a price increase will send clients running. Inflation’s up, my workload has grown, and new prospects still say yes immediately—which probably means I’m underpriced. How do I analyze current value, decide on a new rate, and communicate the change without triggering a mass exodus?”

                    Listen to today’s episode to learn more…

                     

                     

                    SEE ALSO:

                    • Catholic Designer Creates Stylish Apparel Line: What shall it profit a man to gain the whole world but not sell any t-shirts? This designer cast his bread upon the waters and ended up with a profitable fashion line.
                    • Seattle Couple Creates New “Income LiveStream”: When a married couple runs into logistical problems at their wedding, it leads to an innovative service that other engaged couples need during the pandemic.
                    • Role-Playing Pastor Rolls The Dice On $2800/Month Hustle: Listener success story! This Presbyterian minister turns to his lifelong interest in role-playing games to set up a sustainable second income source.
                    • Inspiration is good; inspiration combined with action is better. Now get back to work!

                      Yours in the revolution,

                      <img class="alignnone wp-image-1825" src="https://sidehustleschool.com/wp-content/uploads/2017/04/CG-Sig-Newsletter-300x140.png" alt="cg-sig-newsletter" width="176" height="82" srcset="https://sidehustleschool.com/wp-content/uploads/2017/04/CG-Sig-Newsletter-300x140.png 300w, https://sidehustleschool.com/wp-content/uploads/2017/04/CG-Sig-Newsletter.png 450w" sizes="(max-width: 176px) 100vw, 176px">

                      Resources
                      GET $625 IN FREE TRAVEL

                      Earn 50,000 travel rewards points (enough for 2 round-trip plane tickets or $625 in travel credit). You'll also earn 2x points on all travel and dining spend, with zero foreign transaction fees.

                      I use this card every day all over the world! ✈️

                      Learn More

                      CREATE YOUR ONLINE STORE

                      Create your online store with Shopify using an exclusive discount for Side Hustle School listeners. For a limited time, get a free 21-day trial and a 10% discount for a whole year.

                      Many Side Hustle School listeners are building sites using Shopify's easy-to-learn platform. Try it free today!

                      Learn More

                      Sponsors & Gratitude
                      Learn More With Skillshare!

                      Supporting the sponsors keeps the show free. Today’s episode of Side Hustle School is brought to you by Skillshare. 📷

                      Skillshare is giving Side Hustle School listeners 2 months of unlimited access—for $0.99! Join the 2 million students learning everything from street photography to SEO on Skillshare today!

                      Get Started Here!

                      Like the Show? Leave a Rating!

                      Side Hustle School is for you! If you’re enjoying it, please take a quick moment to leave a rating or write a quick review. It's really easy and it makes a difference! ✅

                      It also makes a huge difference when you tell your friends about the show. Remember, it's 100% free and listener-supported.


                      Here's How

                      Keep in Touch
                      <img class="aligncenter wp-image-1272 size-full" src="https://sidehustleschool.com/wp-content/uploads/2017/03/ChrisGuillebeauSideHustleSchoolFull-1.jpg" width="1076" height="251">
                      There’s a new story every single day on Side Hustle School. Episodes are produced to be short and to the point—I know you’re busy. Be sure you subscribe to get instant notification of the day’s broadcast!

                      Follow

                      Facebook,Instagram,Twitter

                      Email

                      Say Hi

                      From your favorite airport

                      To infinity and beyond,

                      Chris Guillebeau
                      9 min

                    About Side Hustle School

                    From the publisher's feed

                    A daily show for everyone who works a regular job and wants to start an income-earning project on the side. In each episode, listeners will hear a different story of someone who's started a side…