It’s Time to Start That Side Hustle. Here's How.Photo by Corinne Kutz

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There is no better time than now to start the business you’ve been dreaming of. What are you waiting for?

With the virus-that-shall-not-be-named still very much in play, there’s a lot of uncertainty. No one knows what the ‘new normal’ looks like or will look like — and anyone who says differently is selling something.

Here’s the thing: now could be the perfect time to start that side hustle you’ve been thinking about for months (or years).


  • If you’re not a parent, you have more time than ever.
  • If you are a parent, you probably still have more time — you’ll just have to give up those reruns of The Office.
  • Everything is in flux anyway. So, like, why the hell not?
  • How nice would it be to build out a buffer for your 9-5 income?
  • It’s 2020 — there are more free and affordable tools than ever. You could build out a newsletter or consulting gig for practically zero dollars.
  • The online professional community game is strong these days. You can use LinkedIn, RevGenius and ‘micro communities’ to bootstrap your idea and pull in feedback.

The best time to plant a tree was 20 years ago. The second best time is now. 

It doesn’t matter if you’re looking at launching a finance blog, leveraging your LinkedIn following or building a full fledged product. You still need to take your first baby steps.

I’m not some overnight millionaire, but I have built a six-figure content marketing business with a sexy business partner (that’s my wife, y’all). Hopefully I have some tips to share.

This framework won’t get you from $0 to $1 million dollars, but it will get you from $0 to a few thousand per month. That’s all the avocado toast you can eat. Millennials still love avocado toast, right?

Then it’s up to you to build off of the foundation.

Step 1: Turn your idea into action

Actually, strike that. First turn your idea into specific goals. Then turn it into action. Nobody ever draws a straight line from idea to success. You need to have a roadmap in place.

First, create a timeline that aligns with your why. Get fun with it, but also make sure it’s realistic and reflects the purpose behind your project. Some ideas:

  • $1,000 in monthly passive income in one year.
  • Fully replace my full time income in 500 days.
  • Get to 30k LinkedIn followers in three years, leveraging one on one’s and paid content along the way.
  • Reach 5k app downloads on the free version before figuring out how to monetize.

Make this your north star. My first year, it was $40k. Now it’s a multiple of that and I’m still working toward it.

Next up, it’s critical to get — and stay — organized toward your goals. Here’s what’s worked for me.

  • Time block for productivity and for your sanity. We probably could grow our content business two times faster if we bought into the 90-hour work week. But we don’t and shouldn’t. Instead, I try to limit my ‘side gig’ work to a couple of hours in the morning and half days on Sundays. More than that, I plan ahead on how I’ll spend that time so that each hour is blocked for a specific project.
  • Break your goals into weekly “mini” goals. Nobody has time for a full SMART goal matrix. You can still pull out the main principles. If your goal is to hit $10k in revenue by the end of the year, break that up week-by-week. Week one, I’m nailing down pricing and speaking to a handful of pros in my network. Week three, I’m getting messaging on paper and doing more research. Week five, I’m building my initial list for business development. And so on
  • Delegate what you’re not good at (or what you don’t like). If you’re working a 9-5, you’re going to need to be economical with the time you spend on a side gig. This step should only come after you start bringing revenue in, ensuring you don’t spend your own money. Until then, it’s all elbow grease.

Step 2: Validate your idea

Progress beats perfection.

Even best laid plans often go awry, why waste time on laying out your perfect plan? Start by taking action.

How you start taking these baby steps depends entirely on what your idea is. If it’s a product, it could be your beta version. If it’s consulting, it could be your very first client. If it’s an eBook, it could be getting that first draft on paper.

These are a couple ‘sticky’ tips that apply across the board:

  • Free up your mentality capacity for what matters most. No need to set up an LLC or business bank account when you’re trying to land your first client. You don’t need the perfect title to write the first chapter of your ebook. Keep it simple and focus on the tasks that will bring in revenue the fastest. Adjust down the line.
  • Find a concrete way to test your idea. Run $200 worth of ads to your landing page to gauge traction. Set a minimum for your first client. Use Product Hunt to get feedback and jumpstart growth. Something that will put that little voice in the back of your head to rest, and instead say, “Yeah, I got this shit.”
  • Feel out the reception in your network. Ask a handful of people in your network if you can pick their brain. Ask for open feedback on LinkedIn or your Slack community. Just remember: a handful of “this seems like a great idea!” comments doesn’t mean your idea is going to work. See above — find a concrete way to test fast.

You don’t need a $30k retainer to start consulting or the optimal pricing model to launch a product. You just need one paying customer.

Step 3: Start with a basic setup

I made my first $100k as a freelancer on UpWork as a sole proprietor without anything except an annual 1099 and a guesstimation of my employment taxes. It doesn’t have to be complicated.

That said, it did take some mental gymnastics to reorganize everything once we started growing. The key is to leverage free tools along with one or two paid versions that will deliver the most value.

There isn’t really a right or wrong way to go here, but these are my recommendations:

  • Project Management: Good old Google Sheets. No need to get fancy with Trello or right away. You could build out calendars, budgets, project tracking and more with a free, shareable spreadsheet.
  • Payment: If you’re going with services, I love FreshBooks. You could get by with PayPal, but it never feels as professional. Freshbooks starts at $15/month and lets you bring proposals, contracts, invoices and expenses all together. If you’re selling a product, try Gumroad before setting up shop with Stripe or Square.
  • Communication: Slack, Calendly and Whereby. They’re all free and pretty much all you’ll need besides email.

Step 4: Make adjustments for the long term

Again, this is going to depend entirely on what your thing is.

For a product, it’s iterating new versions and potentially building a team. For content, it’s increasing advertising and maybe building a community. For services, it’s figuring out how to scale.

This could be a whole series on its own. These are a few things that worked for us:

  • Increase your pricing. And do it more often than you’d think. If you’re providing value, very few customers or clients are going to bail based on a 20% hike.
  • Start leveraging freelancers. For client work, for things you’re not good at, for things that take time away from what actually makes money. Today, I do very little writing for our clients. I focus on strategy and work with a team of freelancers for execution. I’m not going to write 25k words all on my own, so it’s how we’ve been able to scale.
  • Redouble your efforts on the channels that work for you. Outbound email, LinkedIn, Twitter, micro communities, PPC, social media advertising — the channels for reaching your audience are a little overwhelming these days. Look at what’s worked well and increase your presence there.

Finally, tie it back to the big picture. What are you trying to accomplish, here?

  • Getting some extra cash for beer money? Focus on getting the most money for the least amount of effort.
  • Adding income to boost your investments and financial flexibility? Keep living off your 9-5 income and start saving or investing every penny you make.
  • Building a business for the long haul? Reinvest in the business and start building processes after your first $100k.

None of those are the ‘right’ answers, by the way. It’s just an exercise in aligning your day-to-day actions with your long term goals.

Remember: Success doesn’t have just one definition

When I started focusing on content marketing full-time, my conservative goal was to make a livable income in my first year. I hit that, and then realized there was a whole lot more potential. Over time I stepped back to fill in the blanks: building a team, putting processes in place, getting the right paperwork filed.

Not everyone has to be a Gary Vaynerchuk.

If your goal is to generate $1k passive income and you hit it, you’re a success. If your goal is to get two clients for consulting work and you get two great clients, you’re a success. If your goal is to make money off of web design and you sell a website, you’re a success.

Just keep asking: am I where I want to be, or do I want to go further?