This listener’s new side hustle lost money this year. Hopefully that will change in 2021, but for now—is there a silver lining in being able to deduct losses from his income taxes?




Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. This year, the show includes free guided lessons and listener Q&A several days each week.



Share: #SideHustleSchool

Show notes: SideHustleSchool.com

Twitter: @chrisguillebeau





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This listener’s new side hustle lost money this year. Hopefully that will change in 2021, but for now—is there a silver lining in being able to deduct losses from his income taxes? Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. This year, the show includes free guided lessons and listener Q&amp;A several days each week. Share: #SideHustleSchoolShow notes: SideHustleSchool.comTwitter: @chrisguillebeau To learn more about listener data and our privacy practices visit: <a href="https://www.audacyinc.com/privacy-policy">https://www.audacyinc.com/privacy-policy</a> Learn more about your ad choices. Visit <a href="https://podcastchoices.com/adchoices">https://podcastchoices.com/adchoices</a>

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 hustle—along with what went well, how that person overcame challenges, and what happened as a result. The show is written and hosted by Chris Guillebeau, the New York Times bestselling author of The $100 Startup, The Happiness of Pursuit, and other books.

Sales and Distribution by Lemonada Media https://lemonadamedia.com/  

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 hustle&mdash;along with what went well, how that person overcame challenges, and what happened as a result. The show is written and hosted by Chris Guillebeau, the New York Times bestselling author of The $100 Startup, The Happiness of Pursuit, and other books.
Sales and Distribution by Lemonada Media <a href="https://lemonadamedia.com/" data-stringify-link="https://lemonadamedia.com/" data-sk="tooltip_parent">https://lemonadamedia.com/</a>&nbsp;&nbsp;

A daily show for everyone who works a regular job and wants to start an income-earning project on the side.

Side Hustle School

#1414 - Q&A: Can you deduct side hustle losses from your federal income taxes?

Today’s caller dreads the spotlight but still needs clients. We’ll outline three low-noise, high-trust tactics that bring work to you without daily dancing on social media.

Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. This year, the show includes free guided lessons and listener Q&A several days each week.

Show notes: SideHustleSchool.com

Email: team@sidehustleschool.com

Be on the show: SideHustleSchool.com/questions

Connect on Instagram: @193countries

Visit Chris's main site: ChrisGuillebeau.com

Read A Year of Mental Health: yearofmentalhealth.com

If you're enjoying the show, please pass it along! It's free and has been published every single day since January 1, 2017. We're also very grateful for your five-star ratings—it shows that people are listening and looking forward to new episodes. 😎 🙏🏼 

Today&rsquo;s caller dreads the spotlight but still needs clients. We&rsquo;ll outline three low-noise, high-trust tactics that bring work to you without daily dancing on social media.
Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. This year, the show includes free guided lessons and listener Q&amp;A several days each week.
Show notes:<a href="http://sidehustleschool.com/"> SideHustleSchool.com</a>
Email:<a href="http://team@sidehustleschool.com/"> team@sidehustleschool.com</a>
Be on the show:<a href="http://sidehustleschool.com/questions"> SideHustleSchool.com/questions</a>
Connect on Instagram:<a href="http://instagram.com/193countries"> @193countries</a>
Visit Chris's main site:<a href="http://chrisguillebeau.com/"> ChrisGuillebeau.com</a>
Read A Year of Mental Health:&nbsp;<a href="https://www.yearofmentalhealth.com/">yearofmentalhealth.com</a>
If you're enjoying the show, please pass it along! It's free and has been published every single day since January 1, 2017. We're also very grateful for your five-star ratings&mdash;it shows that people are listening and looking forward to new episodes. 😎 🙏🏼&nbsp;

Ep. 3279 - Q&A: “Do I have to be loud to sell my service?” 

In this week’s First $1,000 segment, four course creators feared ripping their content out of their current system. One weekend migration specialist moved every video and quiz to Kajabi—pocketing a paycheck while their students never missed a lecture.

Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. This year, the show includes free guided lessons and listener Q&A several days each week.

Show notes: SideHustleSchool.com

Email: team@sidehustleschool.com

Be on the show: SideHustleSchool.com/questions

Connect on Instagram: @193countries

Visit Chris's main site: ChrisGuillebeau.com

Read A Year of Mental Health: yearofmentalhealth.com

If you're enjoying the show, please pass it along! It's free and has been published every single day since January 1, 2017. We're also very grateful for your five-star ratings—it shows that people are listening and looking forward to new episodes. 😎 🙏🏼 

In this week&rsquo;s First $1,000 segment, four course creators feared ripping their content out of their current system. One weekend migration specialist moved every video and quiz to Kajabi&mdash;pocketing a paycheck while their students never missed a lecture.
Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. This year, the show includes free guided lessons and listener Q&amp;A several days each week.
Show notes:<a href="http://sidehustleschool.com/"> SideHustleSchool.com</a>
Email:<a href="http://team@sidehustleschool.com/"> team@sidehustleschool.com</a>
Be on the show:<a href="http://sidehustleschool.com/questions"> SideHustleSchool.com/questions</a>
Connect on Instagram:<a href="http://instagram.com/193countries"> @193countries</a>
Visit Chris's main site:<a href="http://chrisguillebeau.com/"> ChrisGuillebeau.com</a>
Read A Year of Mental Health:&nbsp;<a href="https://www.yearofmentalhealth.com/">yearofmentalhealth.com</a>
If you're enjoying the show, please pass it along! It's free and has been published every single day since January 1, 2017. We're also very grateful for your five-star ratings&mdash;it shows that people are listening and looking forward to new episodes. 😎 🙏🏼&nbsp;

Ep. 3278 - First $1,000: Helping Creators Migrate Course Content

This new segment is all about helping you learn the key steps to a new side hustle in 2025, one step or concept per week. It includes activities, examples, and more—and of course it’s all free. Today’s topic: a New York sculptor creates their own market in selling custom firebowls.

Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. This year, the show includes free guided lessons and listener Q&A several days each week.

Show notes: SideHustleSchool.com

Email: team@sidehustleschool.com

Be on the show: SideHustleSchool.com/questions

Connect on Instagram: @193countries

Visit Chris's main site: ChrisGuillebeau.com

Read A Year of Mental Health: yearofmentalhealth.com

If you're enjoying the show, please pass it along! It's free and has been published every single day since January 1, 2017. We're also very grateful for your five-star ratings—it shows that people are listening and looking forward to new episodes. 😎 🙏🏼 

This new segment is all about helping you learn the key steps to a new side hustle in 2025, one step or concept per week. It includes activities, examples, and more&mdash;and of course it&rsquo;s all free. Today&rsquo;s topic: a New York sculptor creates their own market in selling custom firebowls.
Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. This year, the show includes free guided lessons and listener Q&amp;A several days each week.
Show notes:<a href="http://sidehustleschool.com/"> SideHustleSchool.com</a>
Email:<a href="http://team@sidehustleschool.com/"> team@sidehustleschool.com</a>
Be on the show:<a href="http://sidehustleschool.com/questions"> SideHustleSchool.com/questions</a>
Connect on Instagram:<a href="http://instagram.com/193countries"> @193countries</a>
Visit Chris's main site:<a href="http://chrisguillebeau.com/"> ChrisGuillebeau.com</a>
Read A Year of Mental Health:&nbsp;<a href="https://www.yearofmentalhealth.com/">yearofmentalhealth.com</a>
If you're enjoying the show, please pass it along! It's free and has been published every single day since January 1, 2017. We're also very grateful for your five-star ratings&mdash;it shows that people are listening and looking forward to new episodes. 😎 🙏🏼&nbsp;

#1414 - Q&A: Can you deduct side hustle losses from your federal income taxes?

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