How to Start a Side Hustle: Your Comprehensive Guide
Blogging, Entrepreneurship, Freelancing, Location Independence, Remote Work

How to Start a Side Hustle: Your Comprehensive, No BS Guide

Want to learn how to start a side hustle? Welcome! You’ve come to the right place.

Side hustles are growing in popularity with each passing day. People are in search of financial freedom, flexibility, or an exit strategy from their nine to five job, and side hustles present the perfect opportunity.

As many as 44 million Americans reported earning extra income on the side in 2017, with millennials making up the majority.

For many people, their side hustle is simply a stepping stone to self-employment. It’s arguably the least risky way to go about it since it allows people to build up a business while still earning a consistent income from their regular job.

It can also provide job security in general. If you’re earning money on the side, you’ll have the peace of mind that comes from knowing you can provide for yourself financially, even in the event of a sudden job loss.

It can allow you to sock away extra cash each month for an emergency fund, retirement, or a big savings goal like purchasing a home or taking that trip you’ve always dreamed about. It can help you pay down any debt you have much faster.

For some people, their side hustle merely represents a necessary evil–a way to make ends meet in the face of low wages, rising housing costs, and expenses like childcare. It certainly doesn’t help that these factors have led to nearly 50% of all Americans spending their entire monthly paycheck (or more).

For those of us who love to travel, side hustling can mean more available funds to travel with, or a segue into online work that will afford us location independence–in other words, the ability to travel as much as we want because we’ll be able to take our jobs with us.

How to Start a Side Hustle: Your Comprehensive Guide

Victor Gladkov/Shutterstock

You may have another reason entirely for starting a side hustle; maybe it’s just a creative outlet or a way to develop valuable new skills.

Any way you slice it, though, “hustle” remains the operative word. Earning extra money on the side won’t be easy, and if you’re not dedicated and disciplined, you’ll be fighting an uphill battle.

If you have a desire for the freedom side hustling can provide, you have to be ready to work for it.

For me, side hustling has always been about freedom. The freedom to work from anywhere, the freedom to dictate my own schedule, the freedom to take trips whenever I please or simply be there for my loved ones when they need me.

How to Start a Side Hustle This Year

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I’ve read a LOT of articles on side hustles since choosing this lifestyle for myself, but most of them have fallen short in some way. They tend to be pumped up with generalities and vague suggestions that don’t actually lay the groundwork for someone to start their own side hustle.

It’s worth noting, though, that since this site is dedicated to the location independent lifestyle, this post will focus primarily on side hustles that can be done from anywhere–the kind of work you can do with just a laptop and a WiFi connection.

We won’t talk about side hustles like driving for Uber or listing your house on Airbnb, and we won’t go anywhere near multi-level marketing companies (even if the work is based online).

Furthermore, you don’t have to be based in a bustling urban center in order to succeed. You don’t have to be a millennial, either. And you don’t have to work 100-hour weeks to make real progress.

What I will ask of you, though, is to always remember your “why.”

What is driving you to start (and maintain) a side hustle in the first place?

Your reason will be yours and yours alone, and it will sustain you when the going gets tough (because it will be tough at times). Without a clear purpose behind it, your side hustle is likely to fail.

So take a moment right now to write down that “why” and make sure it’s prominently displayed in your workspace.

It’s important that you see it each and every day to remind you of what’s at stake; this will be your motivation to work hard, even on the days you just don’t feel like it.

How to Start a Side Hustle: Your Comprehensive Guide

I remember the very day I made up my mind that I’d never work a nine to five job ever again. I remember how undervalued and defeated I felt, and how underutilized my true talents were in that setting.

I remember how much I yearned for creativity and autonomy. Or even just a basic level of respect.

I was educated, intelligent, and willing to work hard. I knew I deserved better.

So I didn’t have just one “why” but many. I remember that day and those feelings any time I notice my motivation beginning to wane.

Because no matter how hard my life is now as a creative entrepreneur, it’s still a million times better than the alternative and far easier to live with than the regret I would have felt if I’d never taken control of my life by pursuing my own incomes sources.

Tempering Expectations

Let’s get one thing out of the way upfront–starting a successful side hustle will take some serious investments of both time and money.

The exact amounts of each are up to you, but there’s a reason it’s called a HUSTLE.

Because it takes real work and dedication to make it happen. You can’t half-ass it and expect to earn any money, much less replace the income from your full-time job.

It will also take time–this isn’t a “get rich quick” type of deal (because yo, there’s no such thing) so don’t beat yourself up if things aren’t happening as fast as you’d like.

In fact, take as much time as you need to do things the right way.

Furthermore, there may be additional sacrifices that have to be made–less time spent with friends, less time watching your favorite Netflix shows; getting up earlier, staying up later, and so forth.

You can’t expect your lifestyle to remain exactly the same as it is now, but when you achieve what you’re after, you’ll realize those sacrifices were all worth it.

The most important thing is to keep working hard in the face of sacrifices, setbacks, and failures, all the while keeping your WHY in mind.

How to Start a Side Hustle: Your Comprehensive Guide

Picking the Right Side Hustle

When choosing the right side hustle, you essentially have two options:

  1. Choose something you’re already an expert in
  2. Choose something you’re passionate about and learn how to do it better

While it’s obviously important to be skilled at the thing you choose to do for a side hustle, I think it’s almost equally important to be passionate about it.

You’ll be spending a good chunk of your free time working on your side hustle, and if you choose something you loathe just because you already have the knowledge or experience, you may be putting yourself on the fast track to burnout.

So while it may be tempting to do work you already know, take the time to consider whether it’s going to be the most fulfilling option in the long run.

Of course, there are a few other things to consider besides your skill level and your passion.

Is this something you could feasibly charge money for? In other words, is there a need/demand for it? What is the problem you’ll be helping people solve? Who do you hope to serve?

When you’ve got a handful of ideas, run them by a small council of people you trust. Ask for their honest opinions and find out whether they think each idea sounds profitable.

This kind of feedback will be essential to helping you choose the best side hustle!

It also helps to carefully consider your niche and try to be as specific as possible. Will you focus on just one gender? One particular age group or income bracket? Imagine your ideal customer in great detail–what their lives look like, what kind of values they hold, and specific needs they may have.

When I began my side hustle as a social media consultant, I wasn’t just targeting bloggers, I was targeting travel bloggers. But I wasn’t just targeting travel bloggers, either–I was targeting travel bloggers who needed help with Pinterest, specifically.

I became known as a Pinterest expert for that demographic, and referrals were constantly being sent my way.

For help narrowing down your own niche, follow these 7 steps as outlined by the writers at Entrepreneur.

How to Start a Side Hustle: Your Comprehensive Guide

Online Side Hustle Ideas

Need some inspiration to get those wheels turning? Here are some ideas for online side hustles you could pursue.

Online Coaching – Do you have a natural ability to motivate people? Do you have expertise that can help them improve their lives? You might be a perfect coaching candidate. You can help people get in better shape, become more organized and productive, become more confident at public speaking, or anything else you might dream up!

Online Teaching – If you’re the kind of person who wants to teach everything they know, find that skill people want to learn and teach them how to do it. You can teach a language, teach someone how to play an instrument, or teach them how to use a special software program. The possibilities here are endless!

Consulting – If you’ve got special training or experience in a business-related field, why not offer consulting services to business owners? Help them become more efficient in their marketing efforts, help them streamline their communication or systems, help them renovate their website for a better user experience, or improve customer conversions from ad campaigns. Find ways to save them money in the long run and they’ll happily pay you for the service!

Virtual Assistant – People who run online businesses need help with a wide range of tasks, including things like organizing their emails and setting up autoresponders, updating web content, organizing their calendars, and creating beautiful graphics. If you’re tech savvy and have a wide range of skills, you will have no problem finding work as a virtual assistant.

Freelancing – If you have an online skill to offer such as graphic design, web design, photo editing, writing, editing, bookkeeping, accounting, data entry, proofreading, etc, you could become a freelancer. If you don’t yet have online skills such as these, you can easily learn the ropes through e-learning. There is a course for just about everything these days!

Blogging – Do you have a lot of knowledge on one particular topic? Do you love writing about it, talking about it, and answering people’s questions about it? Why not start your own blog? A blog is a great side hustle option, and may even turn into your full-time job like it did for me!

Create and Sell Digital Products – Again, if you have a lot of knowledge about something, put that knowledge to work for you! Build an e-book or an e-course around that topic and sell it online. This can go hand-in-hand with your blogging efforts or be a standalone source of income.

E-Commerce – Did you know there are ways to sell physical products online without ever handling the merchandise yourself? If this idea appeals to you, consider setting up a store that offers print-on-demand products. You fill your store with designs you’ve created (which can be made into mugs, t-shirts, throw pillows, and other items) and the printing service prints and ships them as they are ordered. Another alternative is dropshipping, which is similar in that you never handle the products–they are shipped from a wholesale distributor directly to the customer.

How to Start a Side Hustle: Your Comprehensive Guide

Necessary Prep Work

You may find it necessary to log some hours researching and learning about the field you plan to enter, particularly if you’ve never been in business for yourself before.

I can say from experience that without a basic understanding of business and marketing principles, you will be starting out at a disadvantage.

Here are a few book recommendations to help you gain the confidence to strike out on your own.

Aside from brushing up on business skills, you may want to pursue in-depth training in one specific area. If this is the case, I highly recommend perusing the thousands of online courses offered on Udemy.

There is an enormous range of material to choose from and just about any topic you could imagine. And they hold sales on their most popular courses frequently, meaning you can snag a valuable training for as little as $10-$15.


Remember, though, that at the end of the day, you may never truly feel “ready” to take the leap. There will always be more you could learn. There will always be ways you can continue to improve.

But NOTHING beats the experience that comes from working with real clients. NOTHING will give you better feedback or help you to feel more prepared.

If you find yourself using education as a stall tactic, it’s time to get real. You’ll know you’ve got the skillset. That’s when it’s time to take action. Yes, it may be scary to reach out to that first client, but it will only get easier each time.

Mistakes will be made, and you will learn from them as you go. You may even experience some outright failures. But failure is the true key to success, as long as you don’t give up.

How to Start a Side Hustle: Your Comprehensive Guide

Setting Goals

Now that you’ve got a side hustle idea picked out and you’ve gone the extra mile to learn some business principles that will make things smoother, it’s time to set some goals.

First, set a goal for the amount of time you plan work on your side hustle each week. And get specific! Don’t just write down a goal of 4 hours per week–write down the exact days and times.

If you’re unspecific and think you’ll magically “find the time,” you’re more likely to brush it off in favor of other priorities. Putting this goal on your calendar will make your side hustle a priority and you’ll be more likely to stick to your schedule.

Next, write down a monthly income goal and the date by which you’d like to reach it.

Since you’ve already worked out what your side hustle will be, you should have an idea of how much you plan to charge per client or project. How many clients will you need to work with each month to reach your income goal?

Let’s say you offer a service that costs $250. If your income goal is $1000 per month by April, you’ll need to be booking at least four clients per month.

When broken down this way, your goal will feel more easily achievable and you’ll be able to pave a clear path to get there.

Create Your Online Space

When starting an online side hustle, it’s important for people to be able to find you online. At the very least, it’s worth having a nice website that lists your offerings, past projects you’ve worked on, client testimonials, and some information about you.

It will look professional and help you stand out from your competitors. Beautiful websites don’t have to be expensive, either. You can often get a free domain name when you purchase professional web hosting, and your hosting service can cost as little as $3.95 per month.

Find my full guide on setting up a beautiful blog here.

In addition to a website, it’s important to set up social media accounts as well. This is where you can market your services and connect in a very personal way with potential clients. Creating content and answering people’s questions on these forums will help you establish yourself as an expert in your field.

It’s important that your branding is consistent across your website and all associated social media accounts. If you need help with this, consider hiring a branding coach who can help you refine your message.

How to Start a Side Hustle: Your Comprehensive Guide

In fact, if there’s any part of this process that feels so difficult that it becomes a roadblock to your progress, don’t hesitate to outsource it.

If the idea of setting up your own website makes your head spin, for example, pay someone to do it for you so you can focus on more important things like client outreach.

Finding Your First Clients

The first client is far and away the most important. Once you’ve worked with at least one, you’ll be in a much better position to secure another, and more after that.

But how do you get that first client? It’s probably a lot easier than you think.

Consult Your Network

Offer your services first to your own network of friends and family. If they don’t need your service, there’s a chance they know someone who does.

Social media makes this process especially easy. Write a post on Facebook and another on Instagram and see how quickly the word spreads.

The people who know you will be more willing to give you a chance when you’ve got no experience, especially if you offer them a promotional rate.

What’s even better about this scenario is, it will be less intimidating to ask for a glowing testimonial and a few referrals from someone you know (even if there are a few degrees of separation).


You may be surprised to see this one on the list, but it’s an excellent place to search for your first client.

Put up your own ad detailing the services you offer, but also keep an eye out for job listings that fit your skill set.

It’s easier to pitch yourself to someone you know needs your services than to convince someone of why they need your services. Don’t be afraid to go for the low-hanging fruit in the beginning.

How to Start a Side Hustle: Your Comprehensive Guide

Job Sites

You’ll find most job sites have plenty of freelance opportunities, as well as flexible, part-time, and remote job opportunities. So don’t rule out the traditional job sites like Indeed or Monster.

However, there are many job sites these days that specifically cater to remote workers. Here are a few of my favorites:

Check out this more detailed list of remote jobs sites.

Cold Emailing

I’ll be the first to admit, I hate cold contacting potential clients. It’s uncomfortable no matter how man times you do it, and there’s always a chance you’ll be rejected, or worse, ignored entirely.

Yes, I’d actually rather get a “No” than be ignored altogether.

But both are bound to happen, so toughen up that skin right now, because at the end of the day, cold outreach is still a great way to get your name out there and connect with people who need the service you’re offering.

Here’s a great resource for writing cold emails that actually generate leads.

What About Freelancing Sites?

You may be familiar with websites like Upwork, Freelancer, and Fiverr where freelancers can set up a profile, browse job listings, and connect with potential clients.

While I can’t speak from personal experience, conversations with fellow remote workers have led me to believe that it’s challenging to find work on such sites any more thanks to the high amount of competition and the prevalence of workers who are willing to work for very little.

You don’t want to get caught up in a race to the bottom with people who have no problem undercutting your rates, and you probably don’t want to work for clients who are intent on paying as little as possible.

I wouldn’t necessarily rule these sites out entirely, but you may be better off finding your own clients using the methods outlined above.

Know Your Worth

In the beginning, it’s not uncommon for new freelancers or consultants to charge a lower rate than they’d normally accept. It’s a way to get some experience under your belt and a few positive client testimonials in your portfolio.

But working for peanuts is a terrible long-term strategy, so don’t forget to determine your ideal rate before working with that first client so you know what you’re working toward.

It’s also not a bad idea to let your first few clients know they’re getting a promotional rate, so they understand just how great a deal you’re offering and that your services won’t be priced that low for long.

Then, once you’ve provided exceptional service to your first few clients, start charging your standard rate.

And as you gain more experience, don’t be afraid to continue raising your rates.

How to Start a Side Hustle: Your Comprehensive Guide

When you’re providing a service, you are essentially exchanging time for money. Since there are only so many hours in a day, the best way to scale your business is to provide a premium service to few clients rather than offering an average service to many.

Avoid the trap of taking on clients who don’t agree to your rates just to keep the money coming in.

This will only take away from your ability to find quality clients who actually value your work and your time.

If you don’t have a clue where to even begin when it comes to pricing, do some research. Find others who are offering a similar service and find out how much they charge. Take into account their level of expertise and how long they’ve been doing it.

When you’re new, you won’t be able to charge the same rates as someone who’s been at it for awhile and has the results to justify it, but it’ll give you a benchmark and something to aim for down the road.

Avoiding a Conflict of Interest

While you’re still working your regular job, it’s important to ensure any side gigs you may take on don’t present a conflict of interest.

Each company will have its own policies in this regard, so you may want to keep communication open and honest by asking your manager ahead of time.

Many workers find that as long as their side hustle doesn’t directly compete with the company’s business, doesn’t interfere with their daily duties, and is never worked on during company time, there’s no problem.

It’s never a good idea to freelance with a competitor, and this will usually be clearly spelled out in your contract.

If you decide not to disclose your side job to your employer, tread lightly. Find out what other freelancers had to say about disclosing their side gigs.

Don’t Wait

I have an interview series here on the blog where I talk to people who have gone the location independence route. I ask them things like how they got started, what their process was like, and what mistakes they made along the way.

For the large majority of these people–who are working remotely, freelancing, or running their own businesses–their current job started out as a side hustle.

They did the sensible thing, saving up extra money and building up client lists before ever jumping ship from their regular jobs.

In the final question of the interview, I ask them for the ONE piece of advice that they’d offer to their younger selves.

You know what the answer is 99% of the time?

Start sooner.

If you find yourself dreaming of starting a side hustle but continually putting it off, take this message to heart. Of the dozens of people I’ve interviewed, their single regret through the whole process–from side hustle to location independence–was that they didn’t start sooner.

It may seem intimidating, but once you take those first few steps, your fear starts to melt away. What once felt impossible suddenly feels within reach.

A whole new world of possibilities opens up to you, and your life starts to feel like it belongs to you again.

So go ahead and take a chance on yourself. That’s really what life is all about.

If location independence is your ultimate goal, too, I recommend this post to help you prepare yourself financially for a smooth transition out of your 9 to 5 job.

Did I miss anything? What else would you like to know about starting a successful side hustle? Hit me with your follow-up questions in the comments and let’s continue the conversation.

Loved this post? Pin it for later!How to Start a Side Hustle: Your Comprehensive, No BS Guide #makemoneyonline #sidehustle

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  • Reply Sandra February 7, 2018 at 7:28 pm

    Wow! This post is exactly what I needed! Great advice and a nice motivational kick in the behind. Thank you so much!

  • Reply Matt Burns February 9, 2018 at 2:12 am

    “so don’t beat yourself up if things aren’t happening as fast as you’d like” – I think that’s key, right there. Especially for people who are looking to build a side hustle in the travel blogging world. It’s easy to romanticise and fantasise after that kind of lifestyle. But don’t underestimate the thousands of hours of work that have gone into building it. Thanks for a great read, Leah.
    Matt Burns recently posted…Top US National Parks To Visit In 2018My Profile

    • Reply Leah Davis February 9, 2018 at 4:07 pm

      Very true, Matt! Travel blogging can be tricky to break into, and it takes more time to find success than people probably think. Glad you enjoyed the post!

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