How to Go from Side Hustler to CEO

The pandemic and all the job uncertainties that 2020 came with turned more of us into gig workers and side hustlers than ever before. And now, many of our side hustles are looking pretty attractive as long-term (flexible, remote, what have you) primary employment options.

But how do make the jump from being your own boss as a freelance side hustler to being your own boss as the entrepreneurial CEO of your own company? Those who plan to continue hustling for the long haul need to transition from bootstrappers to business owners, stat.

Here are the top tips and tools to professionalize and systematize your side hustle efforts from three female business owners who've been there and found success.

Set a schedule.

"I highly recommend that my clients put themselves on a schedule," says Keita Williams, the founder of Success Bully, an elite accountability practice dedicated to high-performing Type-A women who have launched side hustles. "You do not have to work a full 40-plus hour week, but choose timing that works for you and your lifestyle, and stick to it."

Side hustlers have to slip in their passion projects between the boundaries of a day job, but CEOs set their own work schedule and decide staff hours around a growth strategy. The transition from being a Solopreneur to an entrepreneur starts with managing your time, so that you know what can be delegated and which high-value actions you must control.

Start by deciding how many hours a week you'll work, then determine your business days. Next, set your hours, even if they change on a weekly or monthly basis. Last, communicate those expectations to clients and employees.

Even on remote or teleworking teams, staff meetings should be regular, check-in calls should be consistent, and time-blocking is your friend. If you don't have employees yet, you likely still have a support system that you rely on to get the job done—freelancers, a significant other, a friend who pitches in on weekends, even your kids who run errands. Take their labor seriously and establish a predictable schedule so you can heighten efficiency. Shared calendars, like Google Calendar, Squarespace Scheduling, and Calendly, can help visualize time commitments.

Find your niche.

Before Rachel Coleman co-founded collegeessayeditor.com six years ago, she offered writing tutoring while working full-time in the United States Senate. She made the transition from operating a side hustle to becoming an entrepreneur in 2015, when she figured out her niche.

"Positioning your startup in the 'demand sweet spot' is critical. When I was initially thinking of starting my own business, I first considered becoming a more traditional writing tutor who helps high school, college, and graduate students with their writing. But when I investigated the landscape, I found it highly oversaturated. During this research, however, I stumbled across a 'college essay editing' site and everything clicked. I looked up the average guidance counselor to student ratio in high schools (although most educational organizations recommend a 250-to-1 ratio of students to school counselors, the national average is actually 424-to-1) and realized how great the demand for college counseling (and its accompanying essay support) was in the United States," Coleman explained. Now, her focus is even more narrowly fixed on non-U.S. students seeking admission at U.S. colleges and universities.

Many side hustlers are committed to doing what they love and the business strategy may come along later. The transition to being a CEO requires a business plan, fully equipped with a sustainability strategy to determine exactly where the activities you love intersect with an in-demand service that people are willing to pay for.

If you don't yet have a business plan or growth strategy, there's no time like the present. Do whatever is needed to legally protect your business, get any required licenses or professional accreditations, and build in maintenance of these operational expenses. For inspiration, look at similar businesses that have thrived or failed, write down your current standard operating procedures, and research high-value activities that will help you reach your goals.

Say 'no' to work you don't want.

After carving out a niche, you'll say 'no' a lot more often. "Stop being a jack of all trades and quit saying 'yes' to every possible client project," says Anais Bock, a leadership trainer, organizational behaviorist (MSc), and the CEO of Bullshit Monsters. "Be willing to alienate most people in order to get a 'hell yes!' from some people (your niche) and become known for that one thing (your product and brand)."

Bock says that business owners have to target their time and attention to clients who are most aligned with their niche. Side hustlers might fear narrowing their customer base will lower their income. CEOs devise a pricing strategy that gradually transitions brand marketing to meet demand. Try drafting a value proposition canvas if you're not sure where to begin.

Raising rates and price lists will accompany the process of pruning your client list, but chances are you were undercharging anyway. Also, don't worry that you'll have to leave your loyal customers in a lurch. Many will make the transition with you. For those that do not, say 'no' with grace and professionalism. Find the right time to close out those projects or recommend professionals in your field who can provide continuity.

Get to the cash faster.

Before bidding her corporate job farewell, Keita Williams successfully brought in eight times her revenue from the previous year in just eight months. Doing so gave her the financial security and the confidence to know that she no longer needed her salaried job to bankroll her business. Since then, her clients have earned over $21 million in revenue, hired additional staff, and left their corporate jobs. She says the key to being a full-time entrepreneur is "shortening the distance between you and the cash. Understand how you make money in your business and focus on duplicating the actions that drive revenue. Save yourself time and busy work by focusing on MMAs: Money Making Activities." For each business, this will be different, but some universal ones include cultivating an email list and streamlining systems.

Side hustlers might shy away from scaling their business, because they don't think they have enough time to devote to earning enough to resign or retire from employee roles. This can create a vicious cycle of underperforming. CEOs know that hiring apprentices, interns, and virtual staff can help. These extra hands can thoughtfully replicate patterns that have worked in the past. CEOs aim to limit the time and effort needed to secure maximum profit. The increased profitability allows entrepreneurs to create value without fretting about overhead and possible downturns.

Become active in professional organizations.

Just because this is your first time owning a business doesn't mean that you're new to the field. Most likely your skills have been cultivated over decades of formal schooling and informal networks. Don't underestimate your value as a freelancer, a sole proprietor, or entrepreneur. Join professional organizations in your area of expertise.

Coleman joined membership organizations like the NACAC (National Association for College Admission Counseling) and HECA (Higher Education Consultants Association), which allowed her to access professional educational webinars on topics like how to market a college counseling practice, how to separate business from personal income, and self-employment tax opportunities.

Most fields have similar entities that support your growth as the CEO and as a skilled professional. Writers might choose the Association of Women Communicators or the Authors Guild. Hairstylists might decide on ProBeauty. Electricians have an entire alphabet soup of options. Even if you can't find an exact match, try a catch-all group like the Professional Association of Independent Contractors or the American Association of Independent Contractors (AAIC), which offer benefits and training that could better position your company.

Bock encourages people to "stop believing that you need an office with a view, business cards, and 20 employees to call yourself a CEO. You can operate a fully-fledged digital business in your flip flops." Side hustlers let imposter syndrome keep them in hiding, but CEOs always demand their seat at the table. Professional associations are key to finding like-minded peers with whom you can learn and partner. These days, you never have to be alone at the top.