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5 Ways to Set Your Side Hustle Up for Growth

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Close-up view of Woman using laptop on her bedThere are a lot of reasons that you might want to pursue a side gig along with managing your main, income-producing, full-time work. Maybe you want to start a business, but you’ve got to keep paying bills while you get it to a profitable level. Or maybe your dream is to freelance, travel, work from home, do a different kind of work, be an indiepreneur, or just have an interesting side thing going on. Whatever your motivation, having a side hustle is a great idea for making a little extra money, building some skills, and even paving the way toward running your own future empire.

If taking your side hustle forward to bigger levels is part of your eventual plan, you need to start from the beginning (or at least from right now) with a good foundation for growth. You can’t build a sturdy structure on a too-small or shaky foundation.

If you’re already well into your side hustle, no worries. You can make changes now to establish a solid, roomy foundation for future growth. In general, smaller things are easier to change: smaller businesses can pivot faster, smaller organizations can reach consensus and change sooner. It’s easier for you to do foundational work and repair now rather than later, when your side hustle has grown into more of a main gig.

1. Take Your Side Hustle Seriously

Successful manTaking a side hustle seriously requires a little bit of faith: in yourself, in your abilities, in your self-discipline, in your end product. If you’re new to your side gig, then having that faith can be difficult and feel presumptuous. My advice is to just ignore those feelings and have some faith in yourself anyway.

The cool thing about having faith in yourself is that you can justify it, at will, with good choices and follow-through. It’s less like blind faith and more like a positive, self-fulfilling prophecy. You didn’t realize that having a side hustle was going to get so spiritual, did you?

Taking your side hustle seriously does not mean you have to talk about it all the time, or brag about your big plans, or be an arrogant jerk in any way. It does mean, though, that you need to dedicate some regular time to it, equip yourself to do the work you want to do, and then put that time into doing it.

You can do those three things—scheduling time, equipping yourself, and doing the work—even if you don’t have paying customers yet. It’s called practicing, and it’s the best way to hone your skills so you can start attracting those paying customers.

2. Make and Keep Realistic Commitments

The second foundational work to do is closely related to the first: keep your commitments to yourself. When you’re starting out in a side hustle, there are two big tendencies you want to watch for and, if possible, avoid. The first is to doubt yourself and your abilities so much that you never put any real effort or time into succeeding. If you take your side hustle seriously, you’ll overcome the self-doubt tendency.

The second damaging tendency is to over-estimate your capabilities, make unrealistic commitments, and then crash and burn into a deep sinkhole of failure when you can’t keep up with your own plans. To counteract this tendency, it’s important that you make realistic commitments and then keep them faithfully.

If you tend to be an overcommitter, do this: whenever you start to make a plan or commitment for your side hustle, divide it by three or four before you make it a real commitment. If you want to start a blog, say, and you’ve decided you’ll blog daily: stop and change that commitment to blogging every three or four days, so biweekly. If you do more than that, great! You’re reaching and surpassing your goals. That’s all positive. But if you hit a busy week at your real job, and you only get to your side gig once or twice, you don’t have to worry about it: you’ve still kept up with your current side-hustle commitments.

The goal is to teach yourself to accurately estimate what you’re capable of doing and to keep yourself from pretending you are superhuman and can go at full-speed, 24 hours a day, every day, forever. You can’t, and you’ll quickly hate your side hustle if it requires that of you. Those kinds of pushes for major progress are good sometimes, but not as the general rule of life; you’ll just get burned out. Work on setting and keeping realistic commitments—a skill you will need even more as your business grows.

3. Build Basic Business Structures

view from above on work deskTo grow your side gig into a legitimate main income-producer and to do so without incurring the wrath of the taxing authorities, you need to build sound business systems.

There are plenty of options and there is a lot of help available, so don’t be intimidated by financial and legal jargon. Instead, do some research and then seek professional help if you hit a wall.

Basic business structures include legal, financial, and the logistics of workflow.

Legal Structures

The options for a legal business structure vary from country to country and, also, based on the type of side hustle you’re doing, how much income you expect to bring in, and other factors (such as whether it’s a service or product-based business, whether you sell locally or globally, and so on). The steps to take here are to research the legal business structures for your locale and then to determine which one meets your needs and what you need to do to set it up. Investing a little money into professional help on this is often a good idea.

Financial Structures

Business financial requirements, such as taxes paid and records kept, often vary based on the legal structure. As you research your legal options, you’ll learn about the financial requirements, too. No matter what type of legal structure you end up with, however, your financial structure will need to include a basic profit and loss statement. It’s also a good idea to start separating your side hustle expenses from personal spending now, so you can keep accurate records. It’s a big, unpleasant task to sort through all your bank statements for legitimate business expenses. It’s much easier to set up a separate business account and use it exclusively for your side hustle expenses and income.


Your workflow includes all the time, space, tools, supplies, and other resources needed to produce whatever it is you’re producing, as well as the way you organize all those resources, the order in which you tackle the steps of production, the methods you employ, and the standards you meet. Building a good workflow is essential to being able to consistently produce high-quality work, no matter what kind of work it is.

If you’re feeling overwhelmed right about now, remember that all these things don’t have to be done right now, at once. One step at a time will get you there. Since you’re already blocking time for your side hustle, start dedicating a little bit of that time, every week, to building these business structures. Make a list of the tasks to do for legal, financial, and workflow structures. It could be that, at first, your only task is to learn about each one, which will help you determine which tasks need to be done next. An hour a week can help you make significant progress without taking on too much.

4. Communicate Professionally

Courteous, quick communication is key to good relationships with your clients. Quick communication does not mean you have to answer emails on the weekend or respond to inquiries within minutes; it does mean, however, that you should establish a habit of regularly checking and responding to all side-hustle communication.

You can choose the channels of communication you open up: as few, or as many, as you want to regulate. Just don’t open any communication channels that you don’t plan to regulate. This includes social media profiles, instant messaging, email, blog commenting, as well as phone calls or text messaging. A social media dashboard like HootSuite or Sprout Social can help you keep track of multiple social media platforms. You can set up a separate side-hustle email account and check it daily. Tools like Zapier and IFTTT can help you streamline multiple inputs into the cache you’ll check most, whether that’s your text messaging or your email account.

Beyond responding in a timely way, of course, you’ll want to establish a courteous, professional tone when you communicate. Sure, be yourself. But don’t dish personal details or otherwise overshare when you’re answering side-hustle inquiries, working out details on a new gig, or talking to a potential new client. Answer the questions, provide the needed information, be friendly and courteous, and that’s all.

5. Think About Growth Phases

Smiling business people reviewing paperwork in officeAs your side hustle starts building momentum, you’ll see new opportunities and potential paths opening up. While you can’t plan for all future options, you can plan out phases of growth. All plans will require some adjustment when they meet reality, but a phased-out growth plan will give you enough information that you’ll have a pretty good idea of what your side hustle will need when it’s time to hit the next level.

Different types of work require different resources for growth. A freelance career as a creative professional, for example, will require more from you in terms of time and availability as it grows. It might not need any more “growth” in terms of space, tools, materials, or even employees. A product-based business, on the other hand, may require increased workspace, storage space, and employed help to keep up with demand as the business grows.

To plan out growth phases, start by estimating the cap on what you can produce at your current level of operation. If you’re side hustling a few hours a week, what is your maximum output in terms of the service or product you generate? Once you know your current upper limit, think about what’s needed to reach the next level: additional time, or space, or help? What do you need to get what is needed?

If it’s time required, you’ll need to think about your options: reducing social obligations so you have more free time to dedicate, reducing work hours at your current job, hiring help for childcare and housework, or some combination. At some point, the next growth phase will require a big change: the jump from side hustle to main gig. You can’t always predict exactly when that change will be needed, but by estimating growth phases, you can have a pretty good idea that you’re getting close.

To Grow or Not to Grow

Building a strong foundation for your side hustle has another benefit, too, one that you might not have anticipated: it can help you figure out sooner if your side hustle will work as a full-time career or not. You may find, as you venture into business structures and growth phases, that you don’t want to turn your side gig into anything bigger. The enjoyment and benefit may be in having something small, a sideline that provides a respite and variation on your day-to-day work.

And that’s great. If you determine that your side hustle should stay a side hustle, you won’t need to waste time on trying to grow it beyond what you can handle on the side. Instead, you can focus on enjoying it as it exists and benefitting from the interest and challenge it brings to your life.

If, as you work on your side hustle, you see growth potential and love the future possibilities, that’s great, too. The work you do now in building a good foundation will equip you to grab those possibilities and run with them when the time comes.

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1 Comment

Posted by Maison Piedfort  | November 14, 2015 at 6:07PM | Reply

Thanks for this! Really needed the encouragement (in the first tip) today.

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