Three years ago I made the decision to quit my job to start a business. Actually, I had already started it as a side-hustle and had to decide if I was going to quit. The decision took place where all big life decisions take place, the TV section of a Best Buy. I don’t remember what I was there to buy. I was walking with my husband and I said, “I’ll buy you that TV if I can quit my job.”

He laughed.

I said, “I’m serious. I think it’s time.”

Deciding to quit your job for a business is not a quick decision

This wasn’t the first time to talk about quitting my full-time job. I was working as a Program Officer with the provincial government while also running a thriving side-hustle. It was the first time I had made six figures in a single year, but it wasn’t an ideal work situation. I spent my days working with community organizations and their projects. I often made video content for LinkedIn while I walked to work (like this one). I even made a video in the stairwell of the government building. After work, I’d eat dinner and then hop on coaching calls or write resumes for clients. I was working from 8 am – 11 pm most days, plus doing work on weekends.

The demand for my work was only increasing and I had a reliable 3-month waiting list to work with me.

I felt like a fraud. I wrote career advice about loving your work, but I was burning out doing both jobs.

I had to make the call. I had a lot of good things going for me to make the decision easier.

Make a “things I have going for me” list

There are people who leap without a plan and wing it. I’m not that kind of person. I have a house and family and wasn’t comfortable quitting the steady job (that was unionized and came with a pension) without a safety net. I made a list of all the things that made it okay and safe to leave my job.

1. I had money saved. Instead of increasing our spending when my income doubled, I put it into savings. I had enough to live for three months without new clients. Plus, I had a four-month-long waiting list which gave me confidence. In my head, I wanted six-months of savings before I quit.
2. I had an additional income stream beyond my side hustle.  I had been contracted to teach a few classes at the University of Winnipeg. This was an additional income that would take the pressure off the business. (Yep, I side-hustled my side hustle)
3. I wasn’t passionate about my day job. When you love your day job and your business, it’s harder to decide. I didn’t love my job and was experiencing guilt about it. I was doing the work, but not bringing energy to it. I was passionate and excited to do the coaching work.
4. I feared being promoted. Even though I felt like I was underachieving, I was still being asked to take on new projects. My manager would highlight my skills to other teams and I was added to committees. When I thought about how I would react to a promotion at work, with more pay and more responsibility, I knew I didn’t want it. It didn’t fit my personal view of success. If anything, it would take me away from my joy-giving work.
5. My side-hustle was energizing. Even though I was working long hours and had no free time, the coaching work felt like play. It was light, it came easy and I felt important doing it.
6. Support people. I had supportive people in my life. I knew people who worked for themselves running small businesses. I knew that if I felt lonely or confused about something, I had people I could count on
7. There was an interest in my business. I was lucky that many people wanted to work with me and my reputation was growing. When I reviewed the data on how many people were inquiring about working with me, and the referrals I was getting, it was stronger every week. I could leave my job in response to demand.
8. Back-up plan. Luckily, my specialty is in how to talk about your work to get hired for ideal projects. I knew I had the skills to land something quickly if the business failed. I checked in with my recruiting friends and talked out a plan B if needed.

How to quit your job for your business

Making the list helped me see what I had going for me, and what I had to think about more. I decided to quit the job.

I scheduled a meeting with my manager and told him that I wanted to leave, but also give him enough notice to replace me. I had hoped to stay for 2.5 months. He requested I stay for four months to wrap up a project I was leading. I agreed. This gave us both time to get ready for my transition. I took on fewer clients in my business to focus on building up systems for my launch. This gave me space in my life.

Nine questions to ask before quitting your job to start a business

If you’re at the point of thinking about leaving your regular job to start (or continue) your own business, work through these nine questions.

1. Do you have enough money to pay yourself and your bills for a few months? How many months of savings feels comfortable for you? This is different for everyone I know some people who were so fed up with their jobs, they quit with nothing. Others want three years of savings. What is comfortable for you?
2. Are you potentially hurting your reputation by staying in your current role? Some people stay in jobs longer than they should as they build the business. If your performance at work is impacted, this can affect how people remember you. If you cant keep it together to at least be a B+ at work, it might be time to jump.
3. Are you known in the new sector? Have you built up your career story brand and idea enough that people in your sector know and respect you? Building a business with zero savings and reputation is hard.
4. Is the side hustle work you love? Does the business idea use your favorite and joy-giving skills? If you find parts of it exhausting as a side hustle, they’re likely to be there when it’s your main job too. What’s your plan for this? Swallow and accept or hire people to help with the parts that aren’t great?
5. Do you have a community or other small-biz people to talk to? It can get lonely out there.
6. Is there a small gig you could get (like teaching or short-term consulting projects) that give you a safety net? Sometimes this takes the pressure off and keeps you out and working with people, just not full time.
7. Do you have the skills, resume, reputation, and network to land something in a few months if you need to? This makes it less scary to make a jump.
8. If you were offered a promotion at work or in your current sector, is that more attractive than your business idea? What I’m getting at is did you start a business because you hate your current job? Could another job make you happy? Is the business idea a reaction to not getting far in your company, and what is stopping you from moving forward?
9. Do you love how you feel in your business? Have you built structures to make sure it pays you enough? Do you know where it’s going? For some people, this is task #1 once they quit.

Having a business idea is a gift

People who are inspired to run their own business and have the skills to do it have a gift. We’re special. If you’re special enough to been chosen to be inspired to build your own business, you have been given a gift. It’s not a mistake as long it’s not about running from something. You’re running to something. It takes guts to admit it and own that. You’re special.

Today isn’t always the right time

If you read the questions above and it makes you uneasy about quitting, cool. Today isn’t the day to quit. Use these nine questions to identify what you need to do to be ready. They can help you see the gaps and work on a strong plan. If you need help figuring out how to establish your brand and build demand for your business, I help with that.  The best place to start is with your stories. 

And if you’re reading this and it made you see that having a job is the best for you, that’s super too. We need people in jobs, your work is just as important and interesting, as long as you’re in the right one. Find out if you’re in an ideal job here.

PS. I did buy him a TV a few months later.