Developing your Own Side Hustle

Laptop Man by Ed Yourdon on FlickrThis guest post is from the guys over at Christian and Shane write mostly about personal finance, self improvement projects, and how to have a fulfilling life on a budget.  Check out their site and learn how you can be an awesome guy or gal in Khakis too!

Just a few weeks ago my side hustles became my full time job. Naturally, I was reawakened to just how important having a side hustle truly is. To me, working side gigs has always been second nature, and finding work to do in addition to my “regular” day to day job came naturally. I might hear a co-worker complain about doing some tedious yard work they had no interest in, or maybe a friend mention someone had a broken computer, or maybe see an opportunity to do some freelance graphic design work, and I always jumped at any opportunity. 

Over time, word of mouth got around that I had certain talents and was willing to trade them for cash and as a result – I had my own steady side hustle(s) going.

I know what you may be thinking: “What about those of us who do not fall so naturally into freelancing or doing your own little side business?”  Well, starting from scratch and juggling extra work with kids, a normal work week, and life in general can be tough.

Allow me to break down how it has all worked out for me, then maybe those of you interested in starting your own little side gig can follow my example and possibly do it better.

Discover What You’re Good At

I know it seems obvious, but figuring out what are you good at, or more to the point, what you are good enough at that you could sell it to someone is the first step. My wife got on a kick where she really liked to make jewelry and I had the great idea that she could consign or sell it to small retail shops around town. After showing off a few of her pieces to a couple friends, we abandoned the idea. 

On the other hand, say you do have a knack for making awesome jewelry and do so regularly as a hobby. You might have just found your side hustle!  Point being – people have to want what you are selling.

For me, I have always been a tinkerer and loved building web pages and designing graphics. I used to spend endless hours of my own time in high school doing so. So making the leap from doing these things for fun to for hire, came naturally.

Maybe you have a knack for engines, cutting grass, building fences, or selling stuff on craigslist.  Whatever it is, capitalize on you skill, and you have now found your side hustle.

Learn How to Grow and Market Your Talents

The next step is actually getting work. I am not much of a salesman. I have never cold called anyone or done a single sales pitch. Instead, I listen out for people needing help, network, and offer free advice. Then I offer to help – which eventually turns into a paycheck. This type of marketing strategy (or lack thereof) does not lead to explosive growth, but over the last five years or so I have seen my business continue to grow and grow. 

If you treat your customer right and make them happy, they will probably spread the word about your services for you. I am also quick to do volunteer work for causes or organizations I believe in and hope that they too will refer me to new customers. I have had mixed success with this, but if it is a cause you care about, why not pitch in?

Now that my freelancing is a full time gig for me, I have began thinking more about proactively pushing my services and how I will go about it. I think the number one move is to keep it simple and personal. I plan on making as much face to face contact with people who existing customers referred me to as possible.

In the end, I think success in business relies on building trust and letting your network do most of the work for you.  Almost all of my “best” customers have come via direct referral from other happy clients. 

Find a Good Work/Life/Work Balance

I have heard my wife complain many times that even when I am home, I am not really at home. Instead, I am nestled in my cozy work corner designing away.  Having your own side hustle in addition to your full-time day job has a nasty way of sucking up all your time, especially as you become more successful.

For me, I love working for myself. The sense of accomplishment I feel developing relationships with clients all on my own, doing a great job for them, then being paid for it all, is a major source of happiness in my life. At the same time, I have to remember my family.

I try to set side hustle work hours for myself. These hours shift a lot for me, depending on what is going on. For a while they were from 5am to 7am on Tuesdays, Wednesdays and Fridays. Before that my side hustle work day was basically all of Sunday morning. Now my side hustle hours are whenever I can squeeze them in between playing with my 3 year-old and changing my newborn baby’s diapers.  I love it!

I think the lesson to take away is that it is important to set rules for yourself and establish a structure. Otherwise you will find your work hours leaking into your family time.  Moms usually aren’t too happy about that.

Make it Legal

I have not had to deal with too many disgruntled customers, but after one close call, I decided I better make my side hustle official. This meant forming an LLC, getting a separate bank account, drafting service agreements to be signed before each project, and keeping solid accounting on the business.

Hopefully you will never find yourself in any kind of legal problems due to your side hustle and freelance work, but should you, make sure it’s the business being sued and not YOU! 

Luckily in my state, setting up an LLC is as simple as going to the Secretary of State’s website, filling out some simple paperwork and sending them a check to cover some fees. There really is little reason to hire a lawyer in most cases either. I used simple internet searches and websites like to guide me.

Never Mix Work with the Side Hustle!

I have been lucky enough to develop some tight relationships with my clients. Some lean on me closely to keep the IT side of their businesses running. Sometimes something might go wrong during the day and I might find a client calling me for support at 2 o’clock in the afternoon on a Tuesday! What is a guy to do?  Do I leave work to take care of a personal assignment?

I made the mistake one time of actually helping a client out while sitting in my cubicle at work. The conversation I had afterwards with my boss was neither pleasant nor fruitful.

While I don’t have to worry about that anymore, my suggestion is, if the side hustle does start finding its way into the normal business hours of the day, set boundaries. In fact, I have decided to never make the mistake of letting a boss know about my side work again. If I do ever get another mid day call for support, I will politely ask them if I can call them back and take a short break. This usually means my lunches and coffee breaks are shared with client work. 

But hey – when this starts happening too much, it’s starting to look like a good time to change that side gig to a full time job!

Get a Side Hustle!

Yes, if you develop a fruitful side hustle, you are going to be putting in a lot more hours, but if it is something you enjoy and you treat it almost as a hobby (that you get paid for) then why not?

For me, my side income has been invaluable. It started helping me make it through college, then grew into a tool to build my savings, and later went on to help me pay for grad school! Then a few weeks back I found myself laid off work and now it’s helping pay the mortgage.

In addition to that, it keeps me active in the community, meeting new people, networking, and developing new skill sets. I also look pretty impressive as a guy coming out of an MBA program and being able to show a proven history of building my own client base and effectively running my own business. For me, the benefits have been immeasurable.

Find something you are good at, enjoy, or are even passionate about and figure out a way to sell it. It is as easy as that. Start out small and keep working.

Have your own side gig or advice for those looking to start out?  Let us know in the comments!


  1. If your side hustle has become your full-time job, sounds like it’s time to find a new side hustle!

    I don’t remember who said it, but “Everybody needs a side hustle.”


  2. Selling kids toys and books on Ebay that I buy from yard sales. After finding so many great things for my own small children I realized I have a knack for it!

  3. Thanks for pointing this out! My husband and I have raised and sold cattle for nearly 20 years in addition to our full time jobs. Our side hustle will become my husband full time job when he retires at age 52 in about a year.

  4. Great post. Actually *getting* side work seems to be the hardest part for most skilled professionals (like plumbers, electricians, auto mechanics, etc). Most of the time it happens (as you mentioned) by word of mouth, and the work trickles in randomly.

    After realizing most of my friends have this problem, my friend and I started a project called SidePros (, where we attempt to alleviate some of the problems with finding side work.

    Hope you (and your readers) find it useful.

  5. Well, after all this time reading your blog, I finally decided it was time to branch out into my own side hustle, with the hopes of it becoming my full time work from home next year. I *never* would have dreamed of this, but for your newsletters and their encouragement and wisdom. I’m now being paid three times as much for the same thing I do every day, and I can do it in my pajamas while the kids sleep. Thanks!

  6. The thing about “side hustles” is that many people don’t do their homework. They think they can turn a passion, a skill/talent or a hobby into a moneymaker.

    But if the demand is limited, too sporadic and/or your supplies and time = prices you can’t get for your product or service, you’re gonna be out both time and money.

    Even with ebay. You do have to spend time learning what is in the market, what people will pay and mastering ebays processes. Plus you have to invest time in photos, writeups and really trying to set yourself apart.

    Contrary to what it seems, sometimes nobody will pay “nothing” for everything.

    Most successful “side hustles” (and I hate that term) are when someone is doing pretty much the same thing they do at a paid, full-time gig, but now they do it as an independent contractor or freelancer.

    The biggest part of the side hustle? Having to hustle to find customers and then, getting them to pay!

    Many times, it’s actually more profitable and less time-consuming to get a part-time job. That is, unless you have a very in-demand product or service and customers willing to pay top dollar.

    The guy who cuts my hair comes to my place. It isn’t all that much cheaper than a salon but I hate salons. And he needs the side hustle because his full-time salon work doesn’t pay him enough due to fluctuations in clients. And as many clients as he’s had for long periods (over 20 years in my case!), even the side hustle isn’t enough by itself to cover his expenses.

    Today, pretty much everyone needs two jobs (and that doesn’t mean you have an upscale lifestyle to support, either.)

  7. This article is right on time. I’m a musician and I started playing piano for churches and doing gigs with local bands on the side. It originally started as a way to help supplement my income while I was in college; but now I’m at the point where it’s going to become my main deal. Everyone should have a side hustle period. Our economy is changing so much that one cannot afford not to.

  8. Sorry to say no christmas for me this year either. Separation, change in jobs, and school, has made almost imposible for me to just survive. I used to love christmas a lot, but now the holidays seem like so dreary. I try and think of it as A Day for Christ, which is how it is supposed to be, but it sure can be hard. Hope everyone else has a better one than me this year and I’ll pray for better days

  9. When I think of side hustles, I think of Lou from my YMCA
    He not only :
    1. Teaches tennis as a pro
    2. Owns a snack bar, by the Y pool ,that is open only in the summer.
    3. Operates a DJ business, they charge $550.00 for 4 hours.
    4. Owns the vending machines at the Y
    5. Owns a sandwich restaurant near the Y (just opened a month ago).

  10. First of all the guys at We Wear Khakis rock, if you are not subscribed to their blog you should be. Side hustles are a huge part of my life and no is about ready to take over my full-time gig so I hope I can make that happen.