How to Get Your Side Hustle Off the Ground

Nearly 40% of Americans now have a “side hustle” or outside source of income beyond their day job, according to one recent survey, and many more are at least contemplating the possibility. Indeed, a Deloitte survey of millennial and Gen Z workers showed that nearly two-thirds of respondents would consider a side gig to supplement their full-time work.

But there’s often a gap between ideation and action. Many professionals who are interested in developing a side income stream find themselves procrastinating.

If you’re interested in a side hustle but are finding it difficult to get started, you need to clarify the source of your hesitation. What is holding you back? As I’ve discovered in working with participants in my Recognized Expert course, there are four common challenges that can derail aspiring entrepreneurs-on-the-side. Here are targeted strategies to overcome each one.

Focusing on the wrong first steps. Looking at the distance between your idea and the finished product — whether it’s a podcast, a coaching practice, an app, or anything else — can seem overwhelming. Aspiring side hustlers will often fret that they don’t have the money to design a fancy logo or website, or get hung up on whether to incorporate as an S-Corporation or an LLC. In the early stages of your business, those are the wrong things to be worrying about. While it’s true that successful businesses do eventually need to have nice websites and proper legal structures, those are complex and expensive steps that can bog you down initially. You first need to determine whether you even have a business — meaning, do customers want what you’re offering?

The first step, as articulated in the Lean Startup methodology, should always be to run a small, inexpensive test to see if there’s preliminary interest (a “minimum viable product”). For instance, if you want to write a book about a particular topic, try writing a blog post first and see what the response is; if you want to start a coaching practice, try to take on a pro bono client — because if people aren’t interested in being coached for free, they’re definitely not going to pay for it.

Lack of confidence. In the early stages of launching their nascent enterprises, aspiring side hustlers often have concerns about their qualifications: the so-called imposter syndrome). It can be useful to survey the marketplace. What skills and backgrounds do other people in the space have? If your qualifications are similar or better, odds are you have a solid base and will be able to pick up what you don’t already know. If your experience level is markedly below others in the field, you could think about taking on a partner whose skills complement your own, or create your own professional development plan to get the training you need to succeed, such as graphic design, programming, project management, or the like.

Diminishing commitment. Many side hustlers start out strong, pursuing their projects with vigor, but find their resolve flagging over time, as they hit inevitable setbacks or discover that progress is slower than they had expected. A major challenge here is that while your day job has built-in external enforcement mechanisms — you’ve told your boss you’ll deliver the report by Friday, and she’ll be upset if you don’t — your side hustle doesn’t.

In its earliest days, the driving force behind your side hustle is probably just you. That makes it difficult for the 41% of people identified by author Gretchen Rubin as “Obligers,” who have extreme difficulty following through on commitments they make to themselves, but are motivated to take action when others are depending on them. That’s why, if you know you fall into this category, you can outsmart your natural tendencies by identifying an accountability partner or mastermind group to ensure you stay on track, encourage you, and harness your natural aversion to breaking your commitments to others.

Time management issues. Almost everyone with an incipient side hustle will cite lack of time as a key reason their venture hasn’t gotten off the ground — though it’s rarely the real reason. “Lack of time” is a (relatively) societally acceptable excuse for not accomplishing one’s goals, and one that makes us feel validated (“I have a busy and important job”) in the process. But most professionals with only one day job actually have more time than they imagine (as my colleague Laura Vanderkam has pointed out, many professionals who claim to work 70-90 hour weeks typically overestimate by 20+ hours). Instead, it’s more commonly a problem of managing the time we do have.

As Georgetown professor Cal Newport points out in his book Deep Work, it’s useful for professionals to experiment with a myriad of time management strategies to discover their own optimal formula for accomplishing meaningful work — in this case, making progress on your new venture. Some may flourish with longer stretches of uninterrupted time (in which case, you might consider taking vacation days to work on your side hustle); others — like me — prefer to schedule a full day of meetings and phone calls, alternating with unscheduled “deep work” days; and still others manage just fine with an hour or two set aside every morning before working their day job.

For many professionals, a side hustle is the perfect way to develop new skills, explore professional passions, and develop new income streams. If you’ve been considering starting your own side business, these strategies will help you break out of the gridlock that ensnares many aspirants and enable you to take action.