The environment we currently live in

One of my professional colleagues recently posted on LinkedIn about the whole idea of “the side hustle,” opening with this unfortunate anecdote: He had encountered a manager who claimed side hustles were for “people not good at their main hustle.” This is an old-school way of thinking, and side hustles are tremendously important these days. 

That’s become an increasingly reality for many reasons: There is a rise of ageism in the workplace, which means drawing income from a single primary job after age 40 becomes challenging. Then, you have issues around mergers and acquisitions; the Sprint/T-Mobile merger, for example, will end up costing about 28,000 people their jobs (while the executives of both companies make a good chunk of change). One of the fastest paths to growth for a company is to acquire another one, but when that happens, certain roles become overlapping and redundant. 

The side hustle isn’t so much something that should interfere with your main hustle — there needs to be an amount of respect and professionalism afforded to your main income source — but it’s more along the lines of thinking of your career as a pipeline, just as sales professionals think of their work. If Opportunity A drops, is there an Opportunity B? As many in various fields have said, develop your network before you need it, not right after you become unemployed. Side hustles are a way to develop your network — and one of them might become your “main hustle” at some point. In fact, that’s likely to happen.

So if you’re building side hustles right now, what do you need to be thinking about?

The questions to ponder regarding side hustle development

These would be some of the big ones to start thinking about:

• Is there a conflict of interest with your full-time gig? For example, I knew someone once who was writing about learning and development, but his main job courted bigger companies that worked in the L&D / instructional design space. Sometimes those companies would go to him directly, because engaging with one freelance option is cheaper for them than engaging with his main company of employment. This created a series of issues and eventually he was fired from that company. Make sure there is not a conflict of interest between main gig and side hustle, and if there’s any potential overlap, make sure that you make it explicitly clear to your current full-time manager.
• Register your business: You can get an Employer Identification Number relatively quickly, which is a good boon for small businesses and the self-employed. There are similar steps, with different names, in Canada.
•  Establish a brand: This is hard and massively time-consuming, so you will not be able to do it overnight. How to begin, though: Start by thinking about what you offer and where people who need that would be spending time. If you offer instructional design as a side hustle, for example, LinkedIn, Twitter, and Facebook are likely better platforms than Instagram. You could get into niche discussions on Reddit and other boards / industry sites as well. Your brand needs to be unique, i.e. you cannot say the exact same stuff everyone else is saying, and it needs to be a mix of visual and text-based, with some video thrown in, as humans are creatures that respond to multiple learning modalities. You can check out brands you admire, but don’t straight copy them. Take elements of them and infuse those elements with your voice.
• Create a proposal and contracting templates: These can be pretty simple, and proposals can start by thinking about your finances (scroll down a bit). Look around at what others are offering. You don’t want to be the lowest in a market because that means you’ll attract mostly people competing on price, and people competing on price tend to — not always — be less-than-stellar client engagements to have. Here’s one self-employment contract template, and here’s another.
• The numbers: This is a series of steps. You need to work out these numbers — >
  • How many hours per week can you devote to side work?
  • How much money would you like to earn from side work in those hours?
  • What are your core offerings?
  • How can you price those offerings to meet the other numbers?

Here’s a relatively simple math breakdown: Let’s say you think you can devote 10 hours/week to a side hustle of consulting on instructional design. In a given month, you’d ideally like to make an extra $2,000 from your side hustle. That means you will be spending 40 hours/month on the side (10 per week) and need to make $50/hour to reach $2,000 (40 x 50). $50/hour is not a huge rate for many businesses, so this is totally doable! You could probably get it from one client, or break it up across two clients and potentially even clear your $2,000 goal.

• How do you find those clients, though? Start with your networks, especially LinkedIn. Explain what you’re doing, what you can offer, and ask if anyone knows of referrals. Message people directly as well. Send emails to old colleagues, confidantes, and bosses you trusted. Work the existing network you have; this can usually land you 1-2 initial conversations (or more!) and those can become clients. Once you get clients, it’s about delivering for them and getting more referrals and recommendations; that’s largely how the self-employed make the hustle work. But as you go through these steps, consider slightly advanced ideas like building an email list around weekly content blasts, using Facebook or Google ads, and more. You want to get a little bit established with people who have a pre-existing knowledge of you before you try that out, though. 
• Get business insurance: Look specifically into errors and omissions coverage.

How will you know when to move “side” to “main?”

There are easy, direct ways to know — i.e. getting laid off at main gig. Then there are more subtle ways to know, i.e. you enjoy the side work more, there seems to be more of it, the relationship with side partners is growing and your main income source seems purposeless and flat. Most people reach a specific point where they inherently know they should switch from Option A to Option B, but it’s obviously a great idea to discuss with friends, significant other, mentors, and more to see if it feels right to someone not experiencing both options daily. 

What else would you add about setting up a side hustle?