How I Started My Side Hustle: The Step By Step Guide – The Worth Project

by admin

Way back in 2015 I was in a miserable job that I hated. I was on a path that wasn’t right for me. I needed out, and quickly.

I needed a side hustle.

Now I know that, thankfully, not everyone hates their job. But hating your job isn’t the only reason to start a side hustle.

Reasons you might want to start a side hustle:

  • Want a career change and a side hustle can help you gain different experiences, without going back to school
  • Need to earn a little extra cash on the side – that summer vacation isn’t going to pay for itself
  • You want to keep doing the same work, but have the flexibility of not doing it full time for one employer
  • You want to learn a new skill that you’ve always found interesting (flower arranging, anyone?)
  • Be really, really bored and surfing the internet for 6 hours a day isn’t cutting it anymore

These are all valid reasons for wanting to start your side hustle.

Ultimately, I think a side hustle is a critical piece of your financial stability. Even if you plan to be employed by a company for the next 35 years, things change.

Your company does layoffs. Your job gets replaced by robots. You fall on financial hard times and that corporate salary just won’t cut it.

Knowing how to make money – on your own – is the best form of financial independence you can have. Even if you never have to depend on it, just knowing that you can make money outside of your paycheck puts things in a completely different perspective.

Here’s where I was:

  • I hated my job,
  • I had debt,
  • and I wanted a meaningful career.

I realized I could be one of those people that over-analyzed and talked about starting something new for years, only to wake up in a decade still talking. Or I could jump in and start something new and figure it out as I go.

So I jumped. It wasn’t perfect – it still isn’t. But if you’re struggling to get started, here’s exactly what I did, what I learned, and what I wish I would have done differently.

Disclaimer: I am by no means a side hustle expert. I’ve started them, I’ve learned from them, and I’m not done building them up and making my mistakes. In fact, The Worth Project is a side hustle that I dream of making into my full-time gig. I’m just not there yet and that’s ok.

This post is for people that are sitting on the sidelines trying to figure out how to get their side hustle into action.

This isn’t a post that is going to take you step by step from starting a side hustle to suddenly earning $1 million per year. I’ll let those spammy Facebook ads tell you all about that.

Step 1: Decide that you will actually do a side hustle

Duh. I know. But hear me out. There are a lot of people who reach out to me and ask how I started. My answer,

“I decided that I was going to.”


We’re all really, really, really busy. I spent 6 months thinking about starting a side hustle before I actually decided to start one. On a slow weekend, I’d go through story after story on the internet from successful people who had started a side hustle and 6 months later were living on a beach in the Caribbean.

I found those stories equally motivating and frustrating. I wasn’t aiming to go live on a beach for the rest of my life – I just wanted to do something different.

After enough weekends of reading about other people doing things, I decided that I’d just start something. Anything.

Step 2: Decide what you want to start with

Because I left my side hustle search wide open, it was a little overwhelming.

I didn’t feel like I had a lot of skills. I couldn’t actually do anything. I’d spent my whole life in corporate America working on things that didn’t necessarily translate to a job I could do on my own.

My work experience included: a CPA who audited financial statements for banks and brand management where I oversaw the running of a brand and helped launch new products.

These jobs were a great experience but it didn’t feel like something tangible I could take to someone and say,

“I can do X for you and I can do it really well.”

So I had to start really broad with my search. I brainstormed for months on these questions:

  • What was I good at (or what did I want to learn)?
  • What did I enjoy?
  • What would my schedule allow?

From these questions I came up with two side hustle ideas:

#1: Writing

I love math, numbers, and money. So to decide that I was going to write was a little confusing for people. I totally get it. But I enjoy writing, I wanted to improve my writing skills, and it was the easiest thing to fit into my schedule.

I was still working full time and traveling almost every week. In order to write all I needed was my laptop and a little time.

#2: Freelance Marketing

I went back to business school to study marketing.

I didn’t love it as a corporate career (you’re often not really doing much of the marketing that you learn in school), but I loved the idea of diving into smaller companies and helping them with their marketing efforts.

I felt like this would be an easy way to get clients because great experience that I could point to.

Step 3: Learn the basics of what you need to know

Though I knew a decent amount about marketing, I still had to fill in the gaps of how to apply this to smaller companies.

I spent a lot of time reading about digital marketing and learning the basics that you don’t learn when you work for a big company that has big budgets.

For example, I knew what Search Engine Optimization (SEO) was – at my old company we hired an agency to do the SEO work for us and I was in charge of approving it. But I didn’t really know how it worked.

I had to learn the basics so I could figure out how to best pitch myself to clients.

I knew nothing about writing: how to pitch and how to write an article for an online reader. I was used to writing corporate memos and, surprise, that has nothing to do with writing for a blog or a company website.

I didn’t spend a ton of time in this learning phase. I wanted to get some basics down and then I knew I’d learn the rest as I went.

Step 4: Ask for opportunities

You can only stay in your little bubble dreaming about opportunities for so long. Eventually, you have to go out and ask for opportunities. This was the hardest part for me – and it still is.

The best place to start asking for opportunities is with your network, though you don’t have to. I didn’t do this and I still managed to land my first clients. Though if I had to do this all over again, I’d definitely reach out to my network first. It will shortcut the process.

Instead of starting with my network, I started with cold emails. Like I mentioned, this isn’t ideal, but it worked.

My goal with writing was to have a few articles published immediately and then build from there.

After writing around 15 articles that were pretty mediocre (Jordan read them and tactfully told me that I really shouldn’t send them), I finally wrote a draft I was happy with.

I didn’t have my own website so I sent this article to 10 different blogs that I really admired. I received responses from maybe 4 sites: 3 were “no” and 1 said, “yes, we’ll take more, and we’ll pay you.”

I officially started writing!

To find a marketing client was a little trickier.

I wasn’t really sure what I could offer or how to pitch a business. Finally, I was watching TV one evening and a reality show came on. One of the women on the show had her own business and was talking about a problem she was trying to solve. I thought to myself, “I can help her!”

I tracked down her email address, introduced myself, sent a link to my LinkedIn profile, told her that I wanted to help with her business (and suggested a few ideas), and asked to meet for coffee.

Eventually, she said yes to meeting with me.

I didn’t pitch a project right away because I still didn’t really know what she needed. Instead, we talked about her business and I pitched how I would approach certain problems to help her find a solution.

From there, I did a lot of research into her business issues and came up with ideas for the solutions. Two years later, we’re still working together.

This wasn’t the perfect way to get started, but it worked.

Some tips for asking:

  • Be clear about exactly what you can do. If I had come in and said, “I can do your marketing!” or, “I can write about anything!” that wouldn’t have gone anywhere. That puts too much work on the person you’re asking. Even if I didn’t know exactly what I would do, I tried to be as clear as possible about my expertise.
  • Follow up, follow up, follow up. I’m still working on this one, but so many of my opportunities have come because I’ve remembered to follow up. There’s nothing fancy about my follow up technique. It’s usually just “a quick note to check in!”
  • Be gracious with the “no’s.” My ego gets bruised and my confidence gets crushed just like everyone else. When I get a “no” I internalize it and think that somehow it means I’m not good enough. If you end up here you have to figure out how to pull yourself out of this and fast. And always send a thank you reply – even if you’re thanking them for that no.

Step 5: Do the work, rinse, and repeat

Treat these first opportunities like gold because that’s what they are.

I worked as hard as I could to completely over-deliver for my first few jobs. I try to over-deliver on everything anyway, but I really put the pressure on myself to do the best work I possibly could.

I agonized over every word in my first few articles. I meticulously went through each detail for my first marketing job. Doing the work and doing it well wasn’t an issue for me.

Where I wish I would’ve acted faster was with the “repeat” part of this step. I was all consumed with the opportunities I had locked down, I didn’t make time to continue looking for new ones.

At the beginning that was OK because I was just getting my side hustle off the ground, but it created some bad habits. I got stuck in the cycle of pitch, get the job, do the job, freak out because I don’t have another job lined up.

Be sure that you don’t put off the “repeat” step.

Side Hustle Lessons Learned

I’ve learned a lot from starting a side hustle and there are a few key things I’m glad I did as well as a few key things I wish I would’ve done differently.

What I’m really glad that I did:

  • I didn’t wait too long to start. If I was still sitting here three years later wishing I would’ve started a side hustle, I’d be so disappointed in myself. Things weren’t perfect (in fact they still aren’t), but I’m glad I didn’t wait to get started.
  • I wasn’t shy about reaching out to strangers. I had zero shame about reaching out to website owners and other small business owners as I was getting started. This helped me to get started quickly.
  • I tried things and dropped them quickly. Actually, that’s not 100% true. I’m glad that I tried a lot of things and dropped the things that weren’t working quickly. But there has been some work and some writing that I’ve held onto for too long, even though I know it was stretching me too thin and not adding value to my business or development.

What I wish I would’ve done differently:

  • Start with your employer or your network if you can. The fastest and best way to get clients is to go through people you know. Former co-workers, classmates, or current friends. Creating a new position for yourself as a contractor with your current employer. My way was definitely the hardest way.
  • I didn’t balance doing the work and finding new clients. This leads to feast or famine. I’d go through waves of having way too much work only to be followed by terrifying periods of no work. Focus on striking the balance sooner.
  • Self-promote a whole lot more. I hate sharing what I’m doing with friends and family. I know, it’s weird, but I don’t love self-promotion. I’m working on this. Get comfortable with talking about what you’re doing, even if no one understands it at first.

Questions I always get asked:

“How did you decide how much to charge?”

I actually didn’t decide how much to charge at the very beginning. Right or wrong, I wasn’t really concerned with that. I wanted experience.

With the first article that I sold, I let the site tell me the rate they paid. To me, at that moment, the money didn’t matter.

As I continued writing and my work came with more formal pitching, I researched rates and would pitch with fees that I felt comfortable with.

For my first consulting client, I put off talking about fees for as long as possible. I wanted to know that I could come up with good ideas and do work that they valued first, and then talk about compensation second.

I structured it like this:

First, I sold them on the idea that I could come up with a good idea if they would just give me access to some of their company information. I did customer research and put together a full presentation of a project I wanted to do for them. They were thrilled.

Second, I set project milestones. The project had small milestones and I laid the whole timeline out for them. I got them to the first milestone, so they could see my work in action, and then we talked about fees.

This worked for me because had I started off quoting a fee, I definitely would’ve sold myself short because I wasn’t confident in my abilities yet.

“Ok, but I have no time. How do I find the time?”

95% of you reading this article can find the time, if you want to. Let me give you an example.

My charming, smart, and super wonderful husband has wanted to try a side hustle for some time. He works long hours and has a long commute. But that doesn’t stop him.

For the last year he’s been waking up at 4:30 am to try out different ideas. His weekends are focused on side hustle work. We put away our TV. We even moved closer to his office to shorten his commute and one of the reasons to do this was to help him commit to his side hustle.

He is determined. And I am (and you are) the lucky recipient of his hard work.

A few months ago, he decided to learn more about the internet and how things work. So he designed The Worth Project website, he’s done the technical side of starting the referral program, he helps proof-read some articles, and he’s thrown himself into learning about Pinterest.

Is this what he wants to do forever? Unlikely. But he’s committed to learning rather than sitting on the sidelines, and I admire his determination.

“How do you keep going when people tell you no?”

A “no” sucks. They can be hard. I’ll get a “no” today and question my whole life for a second before Jordan makes me snap out of my pity party.

I just try to remember that with all of the “no’s” comes a great “yes.” It’s those yes’s that make it all worth it. It’s not easy to keep going after getting a no, but just remember that you don’t fail until you quit. So just don’t quit.

You may also like