How To Turn Your Side Gig Into a Full-Time Business
If you’ve ever thought about stepping away from life as a 9-to-5 employee to go all in with your business idea and embrace life as a full-time entrepreneur, several factors may have prevented you from moving forward. I’ve been there!
To help you learn from my experience, I’ve put together some thoughts and resources in hopes that my journey and the questions I pose will help you determine what’s right for you. Toward the end, I’ll share 8 steps to take if you’re considering going all in as an entrepreneur.
My career journey
As a graduate student in public administration, I advocated for my university to improve its environmental practices. Months of organizing and advocating ultimately made it possible for me to land a role as the university’s first recycling coordinator, and then sustainability coordinator. I pivoted from my previous role in state government as the executive director of the Massachusetts Caucus of Women Legislators, and started what would become many years working in higher education.
How might your activism create opportunities in your career?
Professors, fellow staff, and others in my network started referring students and alumni to me to learn about my career journey. I started leading workshops on careers in sustainability. Before I knew it, I was regularly meeting with people who were seeking career guidance.
After graduating from law school, a degree I pursued at night while working during the day at the university, I transitioned to work as an environmental protection lobbyist at a statewide nonprofit organization, the Environmental League of Massachusetts. So, not only were people seeking me out to learn about how to create a career in sustainability, now they were also approaching me to learn about career paths in environmental protection advocacy and public policy.
Why I launched a business
Since I had a 9-to-5 job, I needed some parameters that would support relational interactions with a substantial meaningful impact.
In addition to career support, contacts were reaching out to inquire about support for coalitions, nonprofits, and businesses, given my experience as a community organizer and advocate. As a consultant, I took on organizational clients to assist with areas such as strategy development, community engagement, communications, and leadership development.
After a lot of thinking about it and receiving some encouragement from some friends, I decided to launch a business so I would have a more formal way to serve people and organizations.
Starting a business organically
By the time I started charging for my services, I had already developed a steady stream of referrals. As people would send people to me for career support, I began telling them that I had launched a business and would be happy to provide assistance for a fee. This took some getting used to, both for me and the people in my network who had come to think of me as a great free career resource.
At first, all of my clients came from referrals. Then, over time, as I created a website, led workshops, and published blog posts and articles on LinkedIn, my visibility as a service provider grew. And within a few years, clients were finding me from a variety of sources.
Questions to ask yourself:
WHO: Who comes to me for my expertise? What are the qualities and characteristics of who I want to serve? Who do I enjoy working with?
WHAT: What do people seek me out for? What do I want to be known for? What steps can I take so that more people think of me for the kind of work I want to do?
Developing my expertise
After moving across the country from Boston to Portland, OR and back, I transitioned into a newly created role leading communications for Boston University Sustainability. Fun fact: my boss was someone I had gotten to know many years earlier when I was leading the sustainability program at Suffolk University.
With my side business, people in marketing and communications increasingly sought me out for my expertise. By this time, I was growing my reputation as a career resource in the following areas:
Sustainability
Environmental protection advocacy
Public policy
Alternative careers for attorneys
Communications
Higher education
Meeting a growing demand for career services
During the COVID-19 pandemic, my business grew. More and more people were evaluating their lives and seeking opportunities to make a great living while doing meaningful work and creating a new level of flexibility for other aspects of their lives. I pivoted to meeting with clients online in order to meet demand from all over, from California to Minnesota to New Hampshire to Florida.
As my revenues grew, I decided it was time to learn more about how to run my business. So, I sought out guidance from SCORE, which provides free mentoring for small businesses.
Receiving support to learn how to grow my business
During one of my initial sessions with my business mentor Paul, an executive with decades of business experience, he asked me a question that really ruffled my feathers.
“How are you going to grow your business while you have a 9-to-5 job?”
Paul, my business mentor
This simple question bothered me so much, and I wasn’t sure why. At first, I was defensive and I pushed back. Sure, my side business income had grown over the past few years, but I had never imagined that it would grow enough to take the place of my full-time job with its salary and benefits.
Exploring life as a full-time entrepreneur
I decided to pay attention to why Paul’s question bothered me so much. As I pondered this, I started envisioning what it could be like to work for myself. I started reading books, articles, and blog posts about self-employment, small business ownership, entrepreneurship, you name it!
I started to think about all the things I could do with my practice if I were able to focus on it more fully. I would be able to:
Focus on co-creating transformational experiences with clients
Invest more time in professional development for career coaching
Serve as a speaker for more events such as workshops and retreats
Put more time into content creation like writing, which I’ve always loved
Continually improve my approach and tools to better serve my clients
Curate a personal and professional life that’s aligned with my values, interests, goals, and strengths (particularly important as someone diagnosed with ADHD as an adult), with more opportunities to work in different settings, aka not feeling limited by the confines of an office
As I envisioned this as a possible life, I felt increasingly called to work as a coach. My work with clients was deeply rewarding, and I wanted to be able to dedicate myself more fully to helping people clarify and achieve their goals. Especially because my clients are mission-driven, working on issues like sustainability, climate change, and health equity, I am motivated to help them connect with work where they’re able to use their skills to make a substantial impact. When they do that, they advance issues that are important to them and me!
I realized that I was so passionate about working with my clients that I could no longer imagine continuing to just squeeze it into early mornings, nights, and weekends.
From employee to entrepreneur: leaving my 9-to-5 job to grow my business
Ultimately, I made the difficult decision to leave my steady salary and great benefits package to go all in and work for myself. But I didn’t leave immediately. I considered what timing would make sense for me and I saved so I could create a runway for myself.
My boss was supportive when I broke the news — he was sad to see me go, but also excited for me and stated emphatically, “I know you’ll do great!” I was grateful to have his support.
We worked out a win-win situation which included me switching to part-time status for a few weeks so I could tie up some loose ends while also having sufficient time to start to focus more on my business.
Leaving my job to fully focus on my business felt refreshing, exciting, empowering, and yes, also scary! I asked myself the typical kinds of questions like, “What if it doesn’t work out? What if I can’t make enough money?”
I’m extremely grateful to the many people who have supported me and believed in me over the past several years including loved ones, clients, coaches, collaborators, service providers, mentors, and colleagues.
Giving my “possible dream” a chance
Two days after my last day at my job, I boarded a plane from Boston to Mexico…because I wanted to and I could! I no longer needed to worry about whether I had enough vacation days to do something like that, or how doing so would impact my workload and colleagues. Instead, I planned to run my business from Mexico while traveling for a couple of weeks.
While in Mexico, I went for a walk with a new friend, and we came upon a sign that said, “un sueño posible,” which means “a possible dream.” And I realized that what I had done, leaving my job, was my possible dream!
Regardless of whether self-employment would sustain me for the long haul, I knew that leaving my job was something I needed to do for my personal growth. Working for myself felt like a piece that had been missing from my life. I craved escaping cubicle life and instead living in a less conventional way that felt more aligned with who I am and how I want to be.
If I had let the fear control me, I wouldn’t have tried life as an entrepreneur, and I knew I would always regret it and wonder “What if?”
What’s your “sueño posible?” And are you giving it a chance?
8 steps to take if you’re thinking about going all in as an entrepreneur
Here are 8 steps for you to take if you’re thinking about going all in as an entrepreneur.
#1 Get clear on your purpose
What drives you? What are you being called to? What problems are people struggling with that you can help with?
#2 Lean into your strengths and interests
What kind of work do you enjoy so much that you’d want to do it even if you weren’t making money from it?
What kind of work could you see yourself doing for many, many hours per day (because at least for the first few years you’re in business, that’s probably going to be necessary)?
How can you grow your reputation as someone with this particular expertise?
#3 Deal with your head trash
Chris, a coach I worked with to help me improve my approach to sales, taught me about the concept of “head trash.” We all have it!
What kind of head trash is getting in your way? What stories are playing on repeat in your head that are preventing you from living courageously?
Once you identify your mindset issues, it’s time to deal with them. Many people find it helpful to work with a coach to help them make progress so they can get past the fear and instead learn to come from a place of love and courage.
#4 Identify your target customers
Who will you serve? What are the demographics and social demographics of the people you’ll serve? What are their values?
Will you serve animals? I have a couple of friends who started businesses that are focused on dogs and “dog parents” and they love what they do.
How are you cultivating relationships with your target population and adjacent populations each week?
It can take a while to figure out your niche and how best to serve your target clients. Get started and allow this to evolve over time as you learn and grow.
#5 Envision the kind of life you want
When, where, and how do you want to be and work?
Entrepreneurship can provide a level of autonomy that is refreshing for many people who are accustomed to working as employees. For me, working when, where, and how I choose was something it was important to get to experience.
For some people, self-employment can feel isolating though, so it’s important to get to know yourself and what kinds of environments you work well in.
Joining a locally owned co-working community was one of the first steps I took after I left my 9-to-5 job, and I’m so glad I did! It’s provided a great way to meet people from a range of industries and occupations. I’ve led workshops there on career clarity, LinkedIn best practices, and other topics. And I’ve been able to connect and learn with fellow members.
#6 Build yourself a runway
Before you leave a job with a steady salary and benefits, it’s important that you build yourself a runway of at least a few months worth of living expenses. This will help to alleviate pressure, which will be extremely valuable in the early days of your business.
#7 Seek out education and mentorship
Don’t try to figure everything out on your own. There are certificate programs, degree programs, workshops, mentorship programs, and coaches who can help you learn how to grow your business.
#8 Hire professionals
As you start making more money, you’ll be able to hire professionals with expertise in specialized areas. Early on, seek out referrals so you can connect with an accountant and bookkeeper who specialize in working with small businesses.
Some key initial steps you’ll likely want to discuss with them include:
Choosing a business structure that makes sense for you
Opening the necessary bank accounts
Preparing to receive payment and issue payments
Utilizing financial management software to track income and expenses
Setting aside funds for paying taxes
Learning to manage your cash flow so you don’t run out of funds
One-on-one support to help you explore if entrepreneurship could be for you
I’ve supported a wide range of people to launch and grow their businesses, including nonprofit professionals seeking to pivot to working for themselves, coaches wondering how to connect with their target clients, and creatives struggling with organizational aspects of running their business.
If you’re interested in exploring working together, I encourage you to reach out.
Resources to help you launch or grow your business
There are a number of organizations that can help you launch or grow your business.
The U.S. Small Business Administration offers a number of resources, including a guide on how to start your business.
SCORE provides free business mentorship to small businesses.
Organizations like Entrepreneurship for All offer accelerator programs, with a focus on underrepresented populations.
Certificate programs and continuing education courses at colleges and universities can help you learn about entrepreneurship.
If you are a woman or person of color, you can look into getting designated through your state and/or city’s supplier diversity office.
Access my reading recommendations for entrepreneurs. These books helped shift my perspective and educate me about best practices for running my business.
