Your 12-month guide to building your side hustle this year

Month by month, roadblock by roadblock, milestone by milestone: Here’s how you start building your empire in 2019.

Your 12-month guide to building your side hustle this year
[Photo: Ali Roshanzamir/ EyeEm/Getty Images]

Editor’s Note: This story is part of our special New Year’s package “Your Future Self,” click here to read the full series. 


Side hustles are “in.” Or as author and founder of The Lonely Entrepreneur Michael Dermer argues, the gig economy is so prevalent, traditional 9 to 5 jobs are done on the side–instead of the other way around. His assessment is backed by facts, since LinkedIn data found 71% of employees report having a hustle for additional income, and 36% find success in pursuing a passion project. Thanks to an uptick in the number of tech-forward and remote-friendly opportunities with lucrative salaries, the drive to start a freelance career or found a company continues to grow.

“Slowly but surely individuals started to color outside the corporate lines and bring to bear what many want: Fulfillment. Pride. Extra cash. Passion. And most importantly the ability to align effort and talent that one expends with results,” Dermer says.

If you want to put your diligence toward your own gig or big idea, the best way to build it is to have a plan. Even if you’re setting your own hours one day, a huge part of entrepreneurism is self-reliance and focus.


Here, experts who have been there and gigged-that provide your 2019 roadmap.

January: Start with a serious self-assessment

If you think having a side hustle is an easy way to bring in extra cash for your dream vacation to Bali–think again. Considering how much work goes into developing an additional source of income, the most important aspect of getting started is figuring out your motivation. And as the CEO of Life Hacks Wealth, Marcos Jacober recommends asking yourself questions to prepare for the psychological shift required to become a bonafide hustler. “[A side hustle will change] how you view what’s most important in your life and [challenge] your willingness to get very creative and do the dirty work on a daily basis,” he explains.
“Are you willing to make sacrifices for this to work? How badly do you want this to succeed?”

He suggests spending time getting to the heart of what is inspiring action–is it financial freedom? The luxury of doing what you love for a living? The hope to make a difference–or disrupt an industry? Perhaps, more dance lessons for your daughter? Whatever it is, write it down and put it in a place you see frequently to keep you on track.


February: Tap into your community

Figure out how you’re connected to people who have the job you already want. LinkedIn career expert Blair Decembrele says since February is often the coldest month of the year in most regions of the country, it’s strategic to use your time cooped up inside to your hustlin’ advantage.

This might be when you start laying the groundwork that’ll help you succeed in the months to come–from updating your social networks to securing a dotcom domain and social media accounts. You can also start cold emailing alumni connections or folks from previous jobs, and ask for referrals, recommendations, or even introductions. The digital footprint will come in handy when you’re in full pitching mode once spring rolls around.

Since you’re online anyway, Dermer also says that February is an ideal month to set specific goals on what you want to achieve–and more essentially–when you want to start taking on gigs. “It sounds boring, right? But it is critical. Gigs disappear quickly if we don’t treat them like true business ventures,” he explains. “Your ability to make your gig successful will depend on your ability to achieve financial goals. This can of course include other goals such as the launch of a website but you should never lose site of the fact that money will create longer term viability of your hustle.”


March: Be realistic about time

Now that you have built your legs–it’s time to turn your attention upwards and work on your juggling abilities. No matter the industry or the type of profession, most people struggle with time management, starting from the early days of school and far into their careers. After all–procrastination will always be tempting, especially when you don’t have a manager keeping you accountable for your gig duties. Since April will be when you’ll finally hit the ground running–more on that soon–fine-tuning the balancing act of full-time work and gigging is the best way to spend March.

Jacober suggests sitting down at the start of each day and writing your hour-by-hour deliverables. This doesn’t have to be all business-minded, since part of hustling is figuring out a work and life balance, so he recommends setting aside time for lunch, stretches, exercise, and so on. As the month wears on, you’ll quickly see what adjustments need to be made: is there enough friend time? Do you have the space for a new project? Are you going to bed too late–or too early? Are you #exhausted? Good, you’re on the right track.

April: Get going

Now that you’ve laid the groundwork for the first quarter of the year, it’s–hopefully–about to pay off. Depending on what venture you’re shooting for, “getting started” can mean a variety of tasks. If you’re a freelancer in any capacity, it’s time to begin pitching and setting up those invites from February that kept getting pushed to the side. Entrepreneurs will be doing much of the same, as they start conversations around investors and perhaps, seeking capital.


During this month, you’ll want to ensure your website is up and fueled with the information needed to validate your experience and of course, start posting on social channels, according to Jacober. Just remember, every little thing you share should have value, since you’re building a brand, a reputation, and trust. “When it comes to social media posting, there is so much content and not enough time to consume it. Don’t just put something out there for the sake of posting. Think of the objectives you want to achieve from it and make it count,” he recommends.

May: Get involved in an association or professional group

The April forecast probably brought a shower of rejections–and one bright, sunny day of “yes.” Since you’ll be reeling off of the progress and feeling pumped, Decembrele says now is a strategic time to join an association or a professional group within your gig’s industry. Since May kicks off summertime, spirits are higher and more people are willing to go out and about for rooftop cocktails, making it a relatively less stressful time to mingle and make connections. Not to mention, make you better versed when you head out to pitch again. “There are often conferences where you can hear from industry speakers, members may have internship or job opportunities, and you’ll be in the know on key issues and policies,” she explains.

June: Get away

Since your side hustle is still in its infancy stages at this point, a two-week luxury vacation might not be in the cards. But, taking a weekend–or if you can, a week–during June to disconnect and reflect. Decembrele explains any hour spend with your loved ones in a place that feeds your passions can help spark creativity and enrich your focus toward your goals. As you will have likely learned by this stage in your gig trajectory, it’s rare for a freelancer to ever take a solid vacation. When you’re away from your phone for too many days, you could lose opportunities that come and go quickly. This may be a worry–and one that’s warranted–but try to spend at least a handful of hours when you’re out of town to pay attention to the culture and beauty that surrounds you, allowing yourself to daydream of the success you can see within sight.


July: Integrate your knowledge into sales and marketing

Since you’ve been networking, you hopefully have learned a thing or two about how to put yourself out there. Much like dating, finding the right gigs, business partners, investors, and, eventually, employees means consistently pivoting, pitching, and repeating yourself.

Dermer says since July can be a slower month with vacations, use the time to home in on your sales and marketing skills. “Once you have the knowledge, you must make it front and center. It should be the first thing anyone hears. The normal bullet points don’t matter: Everyone uses them. It is your unique knowledge that must shine through,” he explains. Or in other words: Figure out how to differentiate yourself from the rest of other people who also seek your hustle. You want to be a journalist? Cool, what kind? You want to help small business build their social media efforts? What type of micro-companies–and what digital channels?

It’s an experience Jess Tatham, founder and lead developer of DevelopHER Designs, knows all too well. When figuring out how she would launch and build her web development company, she knew seeking a niche market she was personally passionate about would be the best route. Though it took plenty of naming brainstorms and some pitfalls before she found her pace, now she has helped countless female executives and entrepreneurs get their big ideas online.


August: Journal and reflect

Okay–you don’t have to put pen to paper, per se, but you should turn off your distractions and go over where you’ve been, what you’ve done and what’s ahead. Remember when you first thought about hustling your way to a new career in January? Look back on those notes and see where you are, two seasons later. This is when exercising your self-criticisms bones is essential to make moves. Jacober explains entrepreneurs should identify shortcomings in their processes to help them work more efficiently and effectively. Are there areas of your growing gig business that you could outsource to make room for more lucrative incentives? What about jobs you’ve been meaning to reach out to–but keep forgetting? Whatever the tasks are that keep falling through the cracks, now is the time to see where you can make changes.

Decembrele says many budding hustlers will feel stressed by this time. To manage the natural anxiety that comes from piecemealing your own empire, she suggests setting aside every week to gather yourself. “Keep those Sunday Scaries at bay by grabbing a pen and paper, and jot down to-dos, work priorities, questions, and so on,” she explains. “Writing down even the littlest notes and reminders can help you focus on the here and now. Spend some time thinking through what is a priority and start there.”

September: Go in with guns blazing

Technically, the last quarter of the year runs from October to December, but most companies start their mad dash to the New Year finish line after Labor Day. Since children return to school and professionals buckle down to meet goals and bring in the last of their clients and income, a side hustle requires the same diligence. Since you’ve been laying out the blueprint since April, you probably have a steady stream of go-to’s who assign or outsource your work, or are helping you build the groundwork for your business. It’s time to further engage with them and see how you can go even bigger before the end of the year by taking on a new project or perhaps, preparing for the holiday season by buying your supplies in bulk. Dermer says now is the time to put pedal to the medal and bring your gig to a new level.


October: Lean into your customer

After 30 days of going full throttle, you can now look at what you’ve made–and figure out how to make it better. And that begins from the outside in. No matter the side hustle, everyone has some sort of customer. For those in creative fields, it’s not only editors or managers who assign their stories, but the readers who critique them. For anyone in sales, it’s the people who fork over their own hard-earned cash for your product or service. For those who are creating something new in the tech space, it’s users and contractors who are making your dream possible.

Jacober says let October be when you double-down on the heart of any gig: the people. “Provide exceptional service and enhance the customer experience in every way you can. This includes follow up and real time experience management,” he continues. “Part of customer service is being a good listener. Don’t rush people through their conversations or complaints. If they bring up things they have done, hand out praise. People don’t get praised enough and are usually looking for it whether they know it or not.”

November: Pay your gratitude

Cheesy, old-fashioned, or not–saying “thanks” goes a long way when you’re competing against many others for the same gig. In fact, so much of transitioning your side hustle into your full-time lifestyle is earning solid recommendations from previous clients who stand by your talents. Word of mouth is powerful, no matter the industry, and often it is the loudest voice in the room. “The best way to keep your side hustle going is by referrals. As silly as it sounds, you want to be in touch with the people who hired you and offer them a discount for continued service or a perk if they refer someone to you,” explains millennial workforce expert and leadership trainer, Alissa Carpenter. “You want to have a stream of clients coming in based on your good work.”


In addition to writing out those “thank you” notes that could result in monetary notes in the New Year, Jacober also suggesting getting ahead of procrastination, since the holidays always disrupt our routines. This can make it far less likely you freak out when you’re traveling home for Thanksgiving, and can’t stop thinking about that email you sent to so-and-so. “Looking at our to-do list as a whole instead of as bite-sized chunks can really cause us to be overwhelmed. When we feel overwhelmed, anxiety grips us. Anxiety slows our emotional responses and our body as a whole, leaving us feeling even more vulnerable and overwhelmed,” he says.

December: Reflect–and set goals

Resolutions may feel like a waste of time, but you don’t have to call ’em that if you don’t want to. Instead, think of them as goals or, rather, answers to the most important questions you need to ask yourself at the end of your first side hustlin’ year, according to Carpenter. She recommends asking: How did it go–really? What worked? What didn’t? Is this something you want to continue? Did you like it? Was the reward worth it? How were your friendships and relationships impacted? Can you continue to build? Is it time to make the leap–and make your side hustle, your only hustle?

If thinking thoughtfully through all of these questions results in a resounding “YES!–then you know you’re on the right track. Carpenter suggests setting three specific, tangible, and impactful goals for the first 90 days of the year.


And then? Well, get back to work. You’re still just getting started.