If you don’t frequent the sort of blogs I do, you may not have heard of this new trend sweeping the nation called, “the side hustle.” If you didn’t already know, a side hustle is a sort of business pursuit that you do on the side of your normal job. It’s a way to earn extra cash or pursue a passion that your normal job may not allow you to. Best case scenario is you do both these things.

The reason I felt compelled to write about this particular subject is that this very website you’re currently reading is, in fact, a side hustle. Believe it or not, this isn’t any of our full time job. And while I’m not in a position to be bragging about how successful we’ve been, I do think there’s something to be said for our existing since June. In that time we’ve posted about 60 articles by our staff and guest writers and I’m happy to say I think we’ve done some cool work.

Why Side Hustle?

What I love so much about side hustles is they give you an opportunity to pursue your passions and also try to make some money outside of your normal job setting. Very few of us twenty somethings are successful entrepreneurs who work for ourselves and set all our own rules so our side hustles are a place to have control and exercise skills we don’t typically use. I, for instance, am not a writer in my 9 to 5. I’m also not the founder. But for this website, I’m both of those things.

But enough about us, let’s talk about you. 

How to Start a Side Hustle

Step 1: Identify Your Objectives

A side hustle should fulfill at least one of these 3 core objectives (and hopefully more):

  1. Personal Fulfillment
  2. Professional Growth
  3. Extra Money

In the beginning I think it’s important to decide which of these matters the most to you. Which of these core objectives could you fulfill while putting the others to the side? Again, the goal is that you could do something that is both fulfilling and gives you extra money. Or maybe helps you grow professionally and is personally fulfilling. But it’s important to have the self awareness to recognize that depending on the season of your life, one of these objectives is probably more important than the other two. 

For instance, if your primary objective is to make money on the side then you may be willing to do something that doesn’t check the other boxes. Maybe this means you drive for Uber or pick up odd jobs you can do at night.

When I started the website, the goal was to help me and the team grow professionally as well as to be fulfilled by doing something we find fun. One day I want to run my own company and this website seemed like a good way to gather a team and work on a project without having to invest a ton of money or take a huge risk in changing careers. Also I love writing so that didn’t hurt either.

Step 2: Identify Your Skills

To speak from experience, the best questions for yourself are probably:

“What am I good enough at to do (mostly) on my own?”


“What do I care enough about to learn how to be really good at it?”

From my experience, the order of these steps is important. If you are really good at something that there is literally no way to make money at (hard to imagine, but maybe it’s true), and your core objective is making money on the side… you may need to develop a new skill.

Also, it’s been important in my journey to understand that the things that could make me some extra money right now may not be the best things for my long term career. What I mean is that driving for Uber could be a good way to make some extra cash on the side, but it’s not helping me develop any of the skills I want to eventually be a successful entrepreneur. So while I may be giving up some money now to focus on a project that isn’t profitable, a long term view might suggest that building leadership skills now is more important for my overall development. This could be the same for you.

Step 3: Find the Margin in Your Life

‘Margin’ here refers to the time you have that’s available. My personal suggestion is that you work in the morning. Having the early mornings to work on How to 20 Something has been a huge help and I’m not sure the website could have ever existed had I not had this time.

If you need help getting up early, check out this post I wrote about getting up early. 

Also, I’d suggest doing a little bit of math here. If you say you have nights free, run the numbers on exactly how many hours of how many days you’re willing to commit. Then see how many hours that is a week, a month. That way you know exactly how much time you have and also how much time you should be accountable for. For instance, I generally try to avoid working on How to 20 Something on the weekends. The weekends are family time for me and I’m able to do that because I know that come 6 am Monday morning, I’ll be side hustling again.

Step 4: Just Start

Originally, this was the whole point of this post. Starting is the most important part—which brings to mind a great quote by one of my favorite actors:

“Great people do things before they’re ready. They do things before they know they can do it.”

— Amy Poehler

I am now, and have always been, the guy with a million ideas. As a kid, my most common thought was, “they should make…(insert crazy toy here).” I still don’t know who “they” were or why they didn’t ever make any of the cool stuff I kept imagining, but they really should have listened to me. And while active imaginations are a thing most adults lose somewhere along the way, I’ve somehow maintained most of mine. For example, yesterday I ‘invented’ a small wooden box for families to store their cell phones in during family dinners and such. I’ve yet to make a prototype but let me know if you want one and I’ll see what I can do.

@@The problem with a million ideas is there’s no time to act on them all. In fact, I’d say a million is 999,999 ideas too many.@@

The reason is that I believe our twenties are a time of doing—not just imagining. And there’s no way to act on that many ideas. There aren’t enough hours in the day. So the trick becomes deciding on one idea or passion and sticking with it until you finish or decide to change course.

You’re not ready. Do it anyways. 

Here’s the thing, I don’t think it makes sense to wait to start until you think you’re ready. “Readiness” means different things to different people, but I think we would mostly agree that being ready is similar to being prepared and quite honestly—there’s much that can’t be prepared for. But the great thing about any side hustle in your twenties is that you’ve got time to figure it out. So start—just start. 

Step 5: Start Again the Next Day

There are those who critique millennials for being too self centered, too focused on what we want out of life and not focused enough on what we’re contributing to those around us. If we’re honest, this is a fair and reasonable criticism that we should keep in the back of our minds. But where I think many people my age get off course is in thinking that the pursuit of their dreams and hard work doing something they don’t like are mutually exclusive. They aren’t.

@@From what I’ve gathered, it seems that doing a lot of things you don’t like is a necessary step to doing one thing you do.@@

Side hustles are no different—it’s not always fun. The only way to silence the inner doubt is to wake up and start working again.

One Final Most Important Thought

Now that we’ve walked through the steps of what it looks like to start a side hustle, I feel I have to leave you with this one big disclaimer. And that disclaimer is that this is as far as I can take you. I am still very much in the beginning of my side hustling days and so I can’t really speak to how this all turns out.

What I can tell you is that I have gained a tremendous amount of self-confidence from this process. Some of the other goals for my life feel more attainable after starting and sticking with a project for 11 months. Sure, howto20something.com may never have a massive following, but I think we’ve done good work and we’ve stayed consistent and that gives me confidence.

Also, I’d like to thank you for reading this whole post (unless you skipped through the boring parts—in that case thank you for reading some of this post).