Decade in Review: My Most Important Moments and Lessons from the 2010s

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As we turn the calendar on a new decade, I thought I’d reflect back on the last 10 years.

To paint the picture of where the 2010s started for me, I was:

  • coming off a great year in business, and had high hopes for the future
  • about to get married
  • blogging at, on a bunch of random topics
  • $150k underwater in our house, which was a huge source of stress

Let’s see what happened next!


Instead of growing toward my goal of $1 million in revenue, profits in my footwear comparison shopping business were cut in half. Technical trouble related to the website were mostly to blame, along with costly web development projects that mostly went nowhere.

In addition:

  • I continued writing my little personal blog, and had a blast doing it.
  • Bryn and I got married!
  • I ran the San Francisco half marathon.
  • I tried (in futility) to negotiate a reduced principal balance on our mortgage.


2011 was a low point in the shoe business. Margins were getting squeezed by higher ad costs, and I was reinvesting what little profits there were into developing a more modern version of the site.


I also:

  • Dealt with affiliate tax law drama, which earned me some press, but ultimately had me renting an apartment in Nevada for a brief period.
  • Started a bunch of unsuccessful websites, and one that stuck: Virtual Assistant Assistant.


Under the new brand, the shoe business rebounded in 2012.

We also lived for free most of the year while going through the short sale process.


2013 was a year of new beginnings, as that’s when I rolled over my old personal blog to Side Hustle Nation and began The Side Hustle Show podcast.

I also:

  • Attended World Domination Summit
  • Took a 5-week belated honeymoon in Japan and SE Asia
  • Experimented with selling on Fiverr, inspired by AnarchoFighter.


This was a busy year, and a year of transitions. I ended up shutting down the shoe business mid-way through the year. It was a tough call, but the writing was on the wall. I’d spent 4 years trying to revive it to its 2009 highs, and it just wasn’t happening.

On the plus side, the Side Hustle Nation stuff was beginning to gain more traction — and was a lot more fun to work on!

In 2014, I:

  • Attended my first blogging conference, New Media Expo, in Las Vegas.
  • Started hosting paid masterminds, the first real monetization of the Side Hustle Nation project.
  • Wrote and launched Work Smarter, a collection of the best online resources.
  • Started a streak of 500 days of cold showers.
  • Did some freelance writing and book editing.
  • Began creating episode-specific lead magnets for the podcast.
  • Went to the first Podcast Movement in Dallas.
  • Gave a TEDx talk.


I remember being genuinely happy in 2015 for the first time in a long time. This was the first year of full-time focus on Side Hustle Nation, which was great for growth.

I also:


Our little hustler was born in early 2016, and took some adjustment!

I also launched Buy Buttons in the fall, and started the tradition of taking every Friday off.


2017 saw:

  • Chris Guillebeau launch Side Hustle School.
  • Me implement theme days and start taking meetings only 1 day a week.
  • Merch by Amazon become the hottest side hustle of the year.


Little Hustler #2 joined us in April. Unlike his brother, he kept all his food down, and was a much easier baby.

This was the year I finally started paying attention to keyword research and SEO. It’s been super fun and rewarding to come up with content you know people are looking for, and have it stick on the first page of Google.

The highlight of 2018 for me was a month-long summer vacation with the family. We spent a couple weeks in Washington visiting the family, and a couple weeks in Mexico. The time off was a great re-set, and I came back really energized.

After we got back, I made:


2019 was a record year in the business, and with hopefully much less fragile income streams than a decade ago. Still, I can’t help but think, this won’t last forever. I’ve seen it before!

My big projects for the year were:

Your Turn

How did the 2010s shape up for you? My hope is you’re better off today than you were yesterday, and that you can keep stacking up those incremental gains for the next 10 years!

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Nick Loper

About the Author

Nick Loper is a side hustle expert who loves helping people earn more money and start businesses they care about. He hosts the award-winning Side Hustle Show, where he's interviewed over 500 successful entrepreneurs, and is the bestselling author of Buy Buttons, The Side Hustle, and $1,000 100 Ways.

His work has been featured in The New York Times, Entrepreneur, Forbes, TIME, Newsweek, Business Insider, MSN, Yahoo Finance, The Los Angeles Times, The San Francisco Chronicle, The Financial Times, Bankrate, Hubspot, Ahrefs, Shopify, Investopedia, VICE, Vox, Mashable, ChooseFI, Bigger Pockets, The Penny Hoarder, GoBankingRates, and more.

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