Seven years ago, I woke up, sent some emails, and went bowling for a friend’s birthday. And I did it all as a full-time entrepreneur. As of July 1, 2012 I was no longer a Procter & Gamble employee, I had officially started working on Humor That Works full-time. And 2,556 days later, I’m still at it.

Over the past seven years, I have: delivered 536 programs, performed 574 comedy shows, published three books, delivered two TEDx talks, spoke in front of 40,000+ people, launched a coaching program, online course, and awards program, visited all 50 states, 27 countries and 6 continents, and, most importantly, have built a sustainable business spreading the word about the power of humor.

But not everything I’ve done has gone according to plan. Below is a look at some of those “accomplishments” in a little more detail, along with the takeaways I’ve gained from each.

I wanted to share this recap not to brag about what I’ve done (you can see many aren’t brag-worthy), but to share the ups and downs of being an entrepreneur, content creator, and idea haver. Not everything you do is going to work, not every project will be profitable, and not every video will be impactful. But if you never put anything out there, you’ll never create the thing that can change the world (or at least one person’s day, year, or life).

21 Lessons from 7 Years as an Entrepreneur

JULY 24, 2012: I did my first paid gig for Humor That Works after making it my full-time job.

The event was a 3-hour workshop for Santander in Dallas, TX that paid me $1,000 plus travel. Going into the event, the organizer acted liked there would be the opportunity to do a lot of different trainings for the group. After the event, I never heard from her again. That may have been because I didn’t deliver on what they were expecting, it was just hopeful optimism on both of our parts, or it was a way to get me to lower my price (like getting paid in “exposure”).

Takeaway #1: There’s never a guarantee for additional work unless it’s in the contract.

NOVEMBER 13, 2012: I uploaded a video called Zombie Tag to YouTube.

The video was a simple demonstration of one of my favorite applied improv exercises. I had little expectation of how many people would see it, I just wanted to share a fun activity. It slowly became a popular team-building video, now with more than 500,000 views. I foolishly used the song O Fortuna to make the video seem epic which means any ad revenue from the video goes to the music owner, not me.

Takeaway #2: You never know what’s going to resonate with people. As a result, create as though the entire world will see it, but only do the things you’d do even if no one saw it.

NOVEMBER 14, 2012: My first “real” book launched.

501 ways to use humor book

I say “real” because I had previously published a collection of quotations, but they were more curation than creation. I self-published 501 Ways to Use Humor, Beat Stress, and Increase Productivity in both print and on Kindle with the goal of providing a resource for people who wanted to use humor but didn’t know how to get started. The book has so far sold 6,123 copies, netting a 3.8 rating on Amazon off of 18 reviews.

Takeaway #3: You can’t have a third book if you never created a first one. Even if it doesn’t go gang-busters, the first attempt helps you learn for the next several.

MARCH 14, 2013: I officially launched my humor coaching program.

The goal was to provide one-on-one coaching for people who were looking to make a change in their life. After the first six months I all but abandoned the idea after discovering I didn’t really love coaching. I had a grand total of 12 clients, three of which were paid.

Takeaway #4: Just because a successful person does something a certain way, it doesn’t mean you have to. Find the things you like to do and focus on those, rather than doing something because you think you’re “supposed” to.

APRIL 3, 2013: I announced the first ever Corporate Humor Awards.

The awards were created to celebrate individuals and organizations that use humor in the workplace. They recognized five individuals and five companies that effectively used humor in creating a better work environment for the humans that worked there. I repeated the awards in 2014, completely ignored them for three years, and then brought them back in 2018 and (soon) 2019. Yes, I wish I had continued the Corporate Humor Awards every year, but I don’t want the inconsistency to stop me from bringing back the awards whenever I have capacity for them.

Takeaway #5: More important than being consistent is being persistent.

FEBRUARY 4, 2014: I had an enlightening lunch with a fellow engineer.

The lunch was with two PhD students at Carnegie Melon University. I had reached out to them because they were also engineers  who were interested in improv. Towards the end of the lunch, one of the guys asked me who managed my website. I proudly claimed I did and asked why. His response was, “When I talk with you now, I get that you’re an engineer and that you focus on humor because it works, and it sounds fascinating. But when I read the site, it seems fluffy and touchy-feely, and doesn’t seem like something I’d be interested in.” I was appreciative of the feedback and it made me wonder how many other people never reached out or considered booking me because they were turned off by the language on the site.

Takeaway #6: You hardly hear the “nos.” No feedback is, in fact, feedback. If something you try isn’t getting a response, it means something needs to change.

FEBRUARY 8, 2014: I delivered my very first TEDx talk at TEDxOSU.

humor at work tedx

Though the talk never went “viral,” it has racked up more 200,000 views and has led to 13 speaking engagements and over $30,000 in revenue. Looking back at the talk now, I still believe in the content but cringe at the delivery knowing that I’m so much stronger as a speaker now. Part of me wishes I had delivered a stronger talk, but that was a great delivery for my skill level at the time. Plus, I’d much rather look back five years and think I’m a better speaker now than look back five years and realize I haven’t grown at all.

Takeaway #7: If you don’t look back at the past five years and at least cringe a little bit, you probably aren’t taking big enough chances or continually improving.

SEPTEMBER 23, 2014: I had my first five-figure event day.

For the first time in company (and my personal) history, I earned over $10,000 in a day. To do so, I delivered a keynote, breakout, and two workshops over the course of one day for a group of project managers at Nationwide in Columbus, OH. It would be two years before my next five-figure day.

Takeaway #8: One success doesn’t guarantee another success, just as one failure doesn’t guarantee another failure. But a peak at one time can give you a glimpse of what the future could hold.

JANUARY 21, 2015: I launched an online course on humor at work.

After three months of planning, shooting, and editing, my first (and currently only) online course went live on Udemy. I hoped that it might lead to a nice stream of passive income and generate leads for in-person workshops… thus far it has netted $1,682 from 1,198 students and zero leads. Despite my insistence that it is not a course on being funnier, it sits at a 4.15 rating (on 45 reviews) with more than a few negative comments about how it doesn’t make people funnier. More than anything, it did force me to put together a cohesive workshop-style program that I used for in-person deliveries.

Takeaway #9: Passive income is very misunderstood; very often it’s delayed income from work you put in a long time ago, and it’s not guaranteed.

AUGUST 7, 2015: My second app, the Perfect Day (now called 5 Daily Habits), launched.

While I hoped others might benefit from the app, the primary purpose was to provide an easy way for me to follow my five daily habits program. My first app, 501 Ways to Use Humor, came out in November 2013 as an add-on to my first book and has made -$723 dollars off of roughly 200 downloads (revenue of $902 minus $1,625 cost to build). 5 Daily Habits has netted -$3,960 (the app is free but app development is not) with over 6,000 downloads, but it has more than paid for itself in keeping me accountable to my short- and long-term goals… that is until I stopped tracking my habits sometime in 2018.

Takeaway #10: Return-on-investment doesn’t always come in the form of money back, sometimes it’s a new skill, accountability, or additional credibility. Also apps are hard.

JULY 17, 2015: I did a talk for sales new hires at P&G.

Since leaving P&G, I’ve returned to the organization for a number of the events, including one for new employees in sales. In the audience for the talk was Adam, a new hire and the son of the president of the National Speakers Bureau, Brian. Adam enjoyed my presentation so much, he called his dad about it and two days later I talked with Brian about being part of his speaker line-up. That meeting resulted in them listing me as one of their speakers and I’ve done five talks with them for more than $25,000. I’m also friends with Adam and Brian.

Takeaway #11: You never know who is sitting in your audience and what opportunities may come when you deliver a good product or program.

FEBRUARY 11, 2016: I completed my 1,000th performance in my 50th state on my 32nd birthday.

performances by year running

The storytelling show in Hawaii was one of the defining moments of my career up to that point as it was the culmination and celebration of months of travels, years of performances, and decades of existence. I never would have guessed that this introverted teacher’s pet would go on to perform in more than 1,000 shows, let alone do it in all 50 states.

Takeaway #12: What starts as a hobby today could become your passion/career/purpose  tomorrow (where “tomorrow” is a metaphor for the future, 24 hours from hobby to career seems unlikely).

APRIL 22, 2017: I gave my second TEDx talk, this time on the skill of humor at TEDxTAMU.

I dedicated nearly four months to prepping for the talk, doing stand-up and speaking engagements to iterate on the message. I felt great about the performance and the end result. On January 2, 2018, six months after the talk came out, it only had 3,000 views. It hit one million views on July 2, 2018, currently has over four million views, and has been an idea worth spreading.

Takeaway #13: Success is rarely instant. Yes, some people “go viral” “overnight,” but often it’s the result of years of hard work before it happens. And yes, luck plays a huge role in success, but the harder you work, the luckier you seem to get.

SEPTEMBER 26, 2017: My second book, The United States of Laughter, came out.

When I started my  nomadic journey on March 1, 2015, I had no idea what it would lead to or why I was even doing it. By the end of trip, I had traveled 159,023 miles, gone to all 50 states, and visited 14 countries over the course of 18 months. I also had such incredible experiences that I felt compelled to write about them. Like 501 Ways, The United States of Laughter was self-published but in a much more professional manner. It’s currently sold 2,220 copies and has a 4.7 rating on 54 reviews. It has led to 22 media appearances and, perhaps most importantly, gave me the opportunity to do a literal book launch.

Takeaway #14: There’s a cliche that asks, “If anyone wrote a book about your life, would anyone care to read it?” Why not do something worth writing a book about, and then write the book.

SEPTEMBER 29, 2017: I uploaded The Cliched Meaning of Life video.

The video is a stand-up bit that involves 100 cliches in 4 minutes exploring the meaning of life. I had spent years perfecting the performance but kept putting off uploading the video as I thought it had the chance to go viral (and maybe even get me on Ellen), and I was scared to find out if it would. The video currently sits at ~7,000 views and I have not appeared on Ellen.

Takeaway #15: Sometimes we hold off on sharing something with the world because the dream that it might work feels better than the confirmation that it won’t. But you can’t watch a video that’s never been uploaded, and holding on to a fantasy prevents you from building a new reality.

FEBRUARY 18, 2018: I delivered a talk at NSA Winter Conference on the Future of Content Creation.

The talk explores what the world of speaking may look like in the future and was well received. In addition to a standing ovation and a few speakers jokingly “bowing” to me, people afterwards told me they could see that talk being given at nearly every tech conference out there… I’ve only delivered the talk one more time, at another speaker event. However, it has prompted me to work on creating the creative assistant I imagine we’ll have in the future, which might be a product or service in the future.

Takeaway #16: Don’t let compliments or insults sway you too far one way or another. They can be helpful pieces of feedback, but they don’t guarantee success or failure. Only your attitude and commitment do.

JUNE 13, 2018: I streamlined my websites into two brands: Drew Tarvin and Humor That Works.

Drew Tarvin became a combination of Drew Tarvin (comedy / blogging), Andrew Tarvin (speaking, authoring), Slash Entrepreneur (entrepreneurship), and Create / Consume (time tracking). Humor That Works (humor at work training) absorbed Humor Engineer (humor work), Humor’s Office (funny office humor), Humor Awards (corporate humor awards), and Understanding Comedy (how to be funny). For those keeping score, that’s two successful sites out of nine that I started. Though none of the other sites really took off, I wouldn’t call them failures either because they helped me explored ideas and many of the posts still exists under the new brands.

Takeaway #17: You will fail more often than you succeed, but often you will only succeed because you’ve failed.

OCTOBER 25, 2018: I stepped down as co-owner of CSz New York.

CSz New York was the first group I did improv with when I moved to New York City. 10 years and over 350 shows later, I was co-owner of the organization and working to build its presence in the city. Eventually, Humor That Works grew big enough that I wasn’t able to commit time to running the organization or performing as frequently as I once did. The group remains one of the most supportive, hilarious, and joyous groups I’ve ever been a part of was one of the biggest things I had “give up” in order to build the business I wanted to.

Takeaway #18: Owning a business is not without sacrifice. Sometimes you have to stop doing the things you really like to do for the things you love to do.

FEBRUARY 1, 2019: The first Humor That Works workshop not delivered by me took place.

The facilitator-led workshop was a version of a communications workshop I had delivered 80 times for the Flatiron School over six years. But workshop #81 was delivered by Vandad, someone who I trained up to do the program. Since then, 22 Humor That Works programs, including one keynote, have been presented by people not named Drew Tarvin, allowing the message of humor to be spread even when I’m not available or already booked.

Takeaway #19: There’s only so much you can do alone. If you want to multiply your efforts, you’ll have to engage or partner with other people. As the adage goes, “If you want to go fast, go alone. If you want to go far, go together.”

MARCH 8, 2019: I gave a presentation on my fifth continent in two months (and my sixth continent total).

After a few years of various conversations with IBM, I got booked with them to do three week-long events in three different countries (US, Spain, and Singapore) for the largest contract amount I had ever recorded (more than twice the amount of money I made my entire first year as a full-time speaker). Rather than just do those events and be done with it, I decided to seek out additional speaking opportunities in neighboring countries, adding a talk in Morocco and a workshop in Australia, giving me five continents in 47 days.

Takeaway #20: When you achieve success, find ways you can build on that momentum rather than rest on your laurels.

APRIL 1, 2019: My third book, Humor That Works, was published by hybrid-publisher Page Two.

humor that works books

The book was a culmination of everything I learned over 10 years regarding the what, why, and how of humor in the workplace. The book launched as a #1 new release and was featured in FastCompany, Thrive Global, and It was named a top gift for Father’s Day by Forbes and one of the best 49 business books for Empowered Professionals. In the first 3 months, it sold 941 copies, garnered a 4.8 rating on 29 reviews, and led to literal book launch version 2. To get all of that, all it took was over $30,000 in publishing and PR services… but it has led to increased credibility, workshop add-ons, and helped confirm a few booked engagements.

Takeaway #21: To get to the next level, you have to be willing to invest in yourself and your business. The payoff may not always be immediate, but it will come eventually (hopefully).


That brings us to today, July 1, 2019, when I wrote this post capturing some of my successes and failures over seven years of working for myself. Reviewing the past septet of years has served as a helpful reminder of the importance of continuing to create. Honestly, I hadn’t remembered all the things that I tried that didn’t go according to plan. By always having things I was working on, I could focus on what worked instead of dwelling on what didn’t.

A sincere thank you to all who have supported me these past seven years, and for the haters who have helped me grow and get stronger. Here’s to another seven (and hopefully more) years full of successes, failures, and everything in between.

In the current economic climate, it seems that just about everyone is trying to find ways to save money and prepare for the challenging months ahead.  I recently challenged myself to live on only $100 for an entire week to see if I could and what I would learn.

I didn’t realize that the project would be so tough, rewarding, and powerful.  Throughout the course of 7 days, I experienced a myriad of emotions, and learned a lot about myself and my spending.  The best part is that I’m sure you would experience the same powerful effects I did.  Being poor for one week can give you amazing insights on how to save money every week that follows, more than passively reading articles such as 15 Tips for Saving Money or even Reviewing Your Personal Finances.  This provides real lessons taught the best way possible – through experience.

Moreso than any of my other projects, I highly encourage everyone to give it a try. Maybe $100 isn’t the right number for you, but based on your current financial habits, try spending 75% less than your normal weekly budget.  A quick tip: take notes throughout that week, because you’re going to learn a lot.

Still not sure if it’s worth trying? Or wondering what you could learn by doing the challenge? Keep reading to see what you’ll learn about saving money by being poor for a week.

Sensitivity to True Cost

When you have a very limited budget, you start to look at everything you spend money on in terms of “true cost” – the cost of the item or service compared to it’s value, and what you’re giving up in order to have it.  I especially thought about this in terms of food. When deciding between a $3 box of cereal or $5 pack of chicken nuggets, you have think of the actual “cost per meal” (the total cost of all ingredients divided by the number of meals it supplies). The box of cereal requires milk (+$2.39), but will also give you 6-8 light meals. The chicken nuggets will likely fill you up more and don’t necessarily require any sides, but will only get you 2-3 meals.

Why It Helps – Learning about true cost first hand will help you make better purchasing decisions in the future.  It’s foolish to spend $100 on something you’ll use only once.  It’s smart to spend $100 on something you’ll use 100 times or more.

Your Image Is Expensive

Living cheaply means choosing functionality over design or style. Though my leather laptop bag is more in style, my backpack can carry more stuff and has the added advantage of being better for my back. Similarly, it’s hard to justify the added cost when two things have equal functionality, but the more stylish one is more expensive- as is the case with wearing glasses versus contacts.

Your image can also take a hit if you go from a position of affluence to one of financial struggles. Keeping up the façade of having money is tough to do and at times not worth the cost. If you work in the corporate world, it may be important to keep a professional appearance. This means remaining clean-shaven, keeping your clothes pressed, and wearing more expensive dress pants instead of shorts. But living cheaply also means swallowing your pride and declining on Starbucks, even if you’re co-workers are going.

Why It Helps – Many fashion items have the highest true cost associated with them, and are often the least functional.  By thinking about the practicality of an item before purchasing it, you can realize if it’s worth the investment and hassle of even owning the item.

Variety Isn’t Cheap

Variety is the spice of life, but not of living cheaply. One of the things I noticed on my limited budget was that I quickly grew tired of having turkey sandwiches and carrots for lunch. But buying items in bulk is cheaper and drives down true cost. It’s hard to justify spending more money on different options for lunch when you know there’s very little money to go around.

Why It Helps – It’s the simple things that really make a difference.  Until you experience eating Ramen noodles every day, or doing the same activity daily, you won’t appreciate how the smallest changes can make a day more enjoyable.

Hard Times Inspire Creativity

As the days progressed and my budget shrank further, I found more creative ways to save money and still be happy.  Whether it’s new ways to cook chicken, or how you can have fun with just a pen and paper, your mind starts to see everyday things in a new way.

Why It Helps – There’s a common belief that you have to have money to have fun and be happy.  Once you accept your financial limitations and start thinking positively, you find ways to still have fun by experiencing the free (or at least cheaper) things in life.

Barebones Living

It turns out that one of the best ways to declutter your life also applies to saving money.  When you want to get rid of the crap of your life, one method is to put almost all of your belongings in a specified place in your home, such as a closet.  Then, as you truly need an item, you retrieve it from the closet.  After a certain amount of time (a couple of weeks), anything you didn’t get out of the closet that isn’t seasonal, you can  safely get rid of.

Well the same method applies to your finances. I realized that I didn’t really miss dining out that much, but that I couldn’t survive even a day without Internet access.  To cut my expenses, I know that I should focus on cooking at home more, not stopping my Internet service.

Why It Helps – If you cut down all of your spending (dining out, subsciption services, alcohol), you’ll learn what you really need, what you really like, and what you were mostly wasting money on.

Reduce, Reuse, Recycle

When you don’t have the money to buy new crap, you start finding uses for your old crap.  With a limited budget, I couldn’t afford to go to the movies.  But that didn’t really matter, because I had plenty of DVDs that I’ve either never watched, haven’t seen in a long time, or didn’t watch the special features for.  Also there are plenty of secondary uses for many items – plastic bags can carry your lunch or serve as garbage bags, junk mail can serve as scratch paper, and baking soda can be used for about 800 things (ok, maybe 60).

Why It Helps – Using that new-found creativity from a restricted budget, you can start seeing how items can be re-used before you even buy them, helping you choose the items with the lowest true costs.

Money Triggers

While trying to stick to my budget, I started to see where I would normally want to spend my money. Once you’re hyper-sensitive to where you’re money is going, you learn what triggers you to spend money in the first place.  Some common triggers include dating (you are, after all, trying to impress the person), friends, alcohol, poor planning (if you have a busy day and forget to pack multiple meals, you either starve or have to dine out), and laziness.

Why It Helps – The only way you’re going to prevent spending money is to know what causes you to spend it in the first place.  By identify the triggers, you can take steps to correct them, such as learning how to relax and have fun without alcohol, or waking up earlier so you have more time to prepare for your day.

Money Isn’t Everything (In Fact, It’s Hardly Anything)

I’ll admit, at the beginning of the week, I was not happy.  I made it a point to fully immerse myself in the experience and really believe that $100 was the absolute max I could spend during that week and for weeks to come.  As a result, as I made sacrifices and tough choices, I becamed depressed and pitied my situation.  But as the week progressed, as I learned ways to cope with my budget and accepted my situation, I realized feeling sorry for myself didn’t do anything to help put food on the table; it just demotived me.  I accepted my circumstances and decided to build from there- it was an example of “yes and” in real life.

Why It Helps – The cliche is that money can’t buy happiness, and you’ll start to realize that’s true.  There’s a reason that even the richest of people end up depressed- material things aren’t the answer.  Living a week without money helps you realize that, and decreases the importance of money in your life.  Sure you’ll still work to make dough, but you won’t put an unwarranted significance on it.

You Can Survive

The ultimate realization you’ll have at the end of the week is that you can survive.  Regardless of what happens, you can make it through it and come out in the end.  I know that I can live on only $100 a week, and even less if I had to.  I hope to never be in that position as I’ve worked hard to earn where I am now, but if something were to knock me down financially, I’d be able to get back up.

Why It Helps – Having the confidence to know you can take a licking and keep on ticking is powerful.  It emboldens you to make stronger choices and bigger risks.  At the same time, it helps you appreciate the important things in life.  No one lays on their deathbed wishing they had more money; they wish for more time with their friends and family, experiencing life.

A Poor Week Leads to a Richer Life

I can promise you, if you go through this experience, you’ll come out feeling richer at the end.  Not only will you actually be richer (you did, in fact, spend 75% less than you normally would), but you’ll also know how you can personally save some more money, and start appreciating the more important things.  Have you tried the challenge?  Post about it in the comments.