Three lessons to know before pursuing a side hustle

Published October 17, 2016   Posted in How to Think

It’s guest post Monday! Side Hustle veteran Claudia from the blog is dropping by today to give us three lessons to know before considering your next (or first!) side hustle. Do you have a side hustle?

Are you thinking about starting a side hustle?  I imagine you’re reading this post because either you’re considering a side hustle, you’ve recently started your hustle, or you’re a Think Save Retire superfan.

Innovation with a side hustle

As a veteran side hustler with more than 10 years of hustling experience, I’ve encountered the same two challenges over and over again: time and value.

Over the last decade, I’ve invested thousands of hours into a variety of side hustles with only the 1099s to show for it.  I’ve sold programs at college football games.  I’ve worked seasonal retail gigs.  I’ve built websites.  Today, I focus on digital marketing, especially SEO.

Many of my side hustles have worked out to be the equivalent of minimum wage jobs.  And if you were to factor in all of the time and money I spent commuting to these side hustles in Your Money or Your Life fashion, I made very little (if anything).

With all of this time invested in side hustling, you would have thought I would have retired early by now, or at the least, be better at managing money.  The truth is, I was bad with money until recently.  I perpetuated an endless cycle of spend and side hustle, spend and side hustle.  I can’t think of a time in adulthood in which I haven’t had at least a job or two and a side hustle trying to make ends meet.

To make matters worse, I didn’t focus on my one lucrative side hustle.  I had a bad case of “shiny object syndrome,” so I took advantage of any and every side hustle that came my way that offered a quick return.

If you’re reading this blog, chances are that you are better at managing money than I was and you likely have a budget, little to no debt, and you’re well on your way to early retirement.  Kudos to you!

Fortunately, I learned my lesson!  Actually, I’ve learned a LOT lessons, including a few about side hustling.

Three lessons to know before pursuing a side hustle

Lesson #1: Put a limit on the time you invest in a side hustle.

Because of a scarcity mindset and mounds of debt, I skipped taking vacations in favor of side hustling.  I worked each day to the point of exhaustion.  I lacked boundaries and my quality of life suffered.  While I love side hustling, I also love hiking and kayaking, neither of which I was doing.

Knowing what’s most important will help you prioritize your time.  And I strongly recommend setting priorities and limits for your side hustle investment.  Use a calendar or some other tool to assign a period of time each day or each week that you use to invest in a side hustle.  Stick to the limit you set for yourself!

If you want to invest only 10 hours a month because you’re also part of a roller derby team and you volunteer at an animal shelter, then stick to 10 hours.  Keep doing things that you enjoy doing that enhance your quality of life.  Side hustling can enhance your quality of life, too, but it shouldn’t consume all of your time.

Lesson #2: Assign value to your time.

If you search online for side hustle ideas, you will find plenty of suggestions.  Lots of these side hustles will sound like fun!  However, these lists do little in the way of helping you find a side hustle that fits in the time you’ve chosen to invest in such an endeavor.  

Once you decide what kind of time you want to invest and you find some side hustles that appeal to you, assign value.  Avoid letting “shiny object syndrome” impact the decision you make about your hustle.  You can’t do every fun-looking side hustle (I know, I’ve tried).  

If you’ve set aside 10 hours a week, stick to one or two ideas that will provide the most value.  Now, how do you decide what provides the most value?

Based on what your time is worth, you can decide which side hustle provides that value.  Too many side hustlers let someone else set their rates.  I advocate for being in control of your time and the value you provide.  If you don’t, someone else is likely to place a lower value on your time.

If you think your time is worth $25 an hour, focus only on opportunities that you are confident will compensate you at a rate of $25 an hour.

If you think your time is worth $125 an hour, focus only on opportunities that you are confident will compensate you at a rate of $125 an hour.

Lesson #3: Choose a side hustle.

After you’ve decided how much time you want to invest and what your time is worth, consider the plethora of side hustles out there.  As you sort through ideas, you may factor in whether you want to work from home, a co-working space, or somewhere else.  You may also consider resources at your disposal, like a car, a computer, and Internet access and whether or not you can/want to put these to use in a side hustle.

After you’ve narrowed down the list of potential side hustles you may pursue, see if any of these side hustles align with your value and the time you’ve allocated for a side hustle.  I created a simple spreadsheet you can also use to compare side hustle opportunities in terms of both time and money.

Within this side hustle comparison spreadsheet, you’ll find a list of side hustles and estimated hourly rates.  In the first tab of the spreadsheet, I set the column “Amount You Want to Earn” to be the same so you can estimate how much time you need to invest in each side hustle to earn an extra $1,000 each month.  In the second tab, I took the same information and set the column, “Hours You Need/Want to Work” to be the same so that you can see how much money can you earn with the hours you’ve allocated for your side hustle.

Feel free to copy the spreadsheet and input the side hustles you are considering.  Having a spreadsheet like this years ago would have made it much easier for me to hone in on exactly what it was I wanted to be doing.

What questions do you have about side hustling?  Do you have any tips or recommendations for aspiring side hustlers?

Claudia trains and coaches aspiring side hustlers to become digital marketing consultants via online training courses she created, which you can learn more about at or via a free email course.

We track our net worth using Personal Capital


17 responses to “Three lessons to know before pursuing a side hustle”

  1. I’ve only had a few side hustles in the past. I ref’d weekend basketball tournaments a couple summers. That was fun and it was some decent money. But you are right about finding one that is worth the time and effort. Thanks for sharing the comparison spreadsheet, I look forward to browsing!

  2. Apathy Ends says:

    Thanks for the tips – the only side hustling I have done to date is work on my site but that also crosses into a hobby.

    I like your approach to setting a value for your time and searching for opportunities that meet or exceed. My biggest hesitation to the bulk of the side hustles out there is I value my time more than the money

  3. Mr. PIE says:

    When we reach FIRE, I always joke that Mrs. PIE should ramp up her side hustle of awesome cake baking and decorating. But she replies with the reasonable argument of ” would you like to be delaying a vacation or road trip such that I can get a wedding cake out urgently to a soon to be young married couple?”. It is that aspect of time versus prioritizing other things in your life. Invariably sounds good but when you think of priorities, it gets tricky. Sounds like you have learned a great deal through experience of hustling and it is not a bed of roses by any stretch of the imagination.

    • Ooo…definitely love this idea! Wedding planning happens so many months (or even years) in advance, so I imagine that she’d have those dates set in advance. She could be super exclusive, doing only a handful of weddings each year! 😉

  4. Yes yes yes. I think a lot of people get caught up in the idea of side hustles without planning out the actual return. A side hustle is still a business, and businesses need to be profitable. You have to know when something is worth the time and effort.

    • You are so right. A side hustle is essentially a bootstrapped business, so it’s best to run it as such. Assessing whether or not a side hustle could be a full-time business could help differentiate gigs that are worth it and those that aren’t (even if one isn’t interested in going into it on a full-time basis). Thanks for the feedback!

  5. Ms. Montana says:

    Finding that time/value ratio is SO hard. Especially when your side hustle starts costing you extra in other subtle ways. There are only so many hours we can work before we start buying take out food or eating junk. I try to deny it, but it’s true. And all the extra hours start costing us in those other ways.

    • You’re right! When I was hustling multiple gigs, I found myself stopped for takeout all the time! I think that’s why it’s so important to set limits to what can one can reasonably achieve without sacrificing health, money, etc.

  6. Great guest post Steve! I’m always thinking about different side hustles, but usually they seem to need far more time than I have.

    Thanks for the great post!

  7. […] you read my guest post over at Think Save Retire, you’ll see what I learned from side hustling as much as I have […]

  8. Thanks for the guest post Claudia. I’ve been working the side hustles myself using sharing economy websites, like Airbnb. For myself, my key to side hustling is basically three fold: (1) I find them fun, (2) they incorporate tasks I’m already doing or should be doing, and (3) they give me a side benefit beyond just making money.

    So as an example, I’ve been doing Airbnb lately. I find it fun to meet new people. I already have a spare room in my house and it doesn’t take me very much time to set up a guest room for a new guest. And my house has never been cleaner. You know those days when you just let your house turn into a pigpen or let dishes pile up? That doesn’t happen for me anymore.

    Or with my dogsitting adventures. I already own a dog, so petsitting a second dog doesn’t really add any more time to my daily schedule. Walking 1 dog isn’t really all that different from walking 2 dogs. And as a bonus, I get to play with a second dog!

    • Wow! I LOVE your enthusiasm for your various side hustles. Taking advantage of the sharing economy/gig economy is what I’m all about, especially when you highlight the benefits that you did. I am definitely prone to letting dishes pile in the sink, so I just love your Airbnb solution. That’s great!

  9. […] how to find lucrative opportunities? Basically, I learned the hard way. I wasted a lot of time with side gigs that didn’t pay well.  You can avoid making the same mistakes I […]

  10. […] worth your time.  I’ve read a lot of blog posts about side hustles and I’ve also tried lots of side hustles over the years.  Many side hustles pay too little and require too much time.  If you want to […]

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