Nowadays it seems everyone has a side hustle. People look for a way to make extra money. Maybe they want to start their own business but aren’t ready to give up the stability of their main job. So how do you know when it’s time to let your side hustle become your main hustle? Let me tell you my story.

Soon after I graduated from high school, I was on the hunt for extra money.  I fell into mowing lawns because there were plentiful opportunities in the neighborhood that I lived in.  Plus it was something that I had done in the past.  At that point in my life, I still lived at home with my parents. I only had one small bill to pay each month.  In that circumstance, my side money grew into full-time money very gradually, over a few seasons.  There was no rush and no real pressure to produce at any certain rate.  That situation is no longer my situation and for many of you reading this, it isn’t your situation either.

Let’s go ahead and fast forward to a few years ago, more specifically October of 2015.  

At this point in my life, I was married with two kids and I had a well paying corporate job.  Things were comfortable for my wife and highly uncomfortable for me. This is mainly because I was unfulfilled and not thrilled about the idea of being confined inside of someone else’s walls.  Before we go any further and talk about what I did next, let’s take a quick look at my reality.  

I had bills, lots of them, and we were living on the high edge of our means like most Americans.  There was a little money in savings but nowhere near enough to live on for more than six months.  We had a plan for me to make money, but no extra money coming in.  Back then, I often professed that side hustles were for people who were too scared to take the plunge.  Man, I was an idiot…no doubt.  I have learned a tremendous amount since then. The only way that I could have done so was through taking chances and doing things.  A theory has no real value in entrepreneurship, so focus on getting as much actual first-hand experience as you can.  

I quit that job in October of 2015 and I was out of money the following March. I had no real plan and additional money coming in at all.  Oops.  Many of you may fear a similar outcome for you and your family.  This fear is why most people will never leave the role of an employee and assume the role of an employer.  

I now embrace the side hustle and recommend it to anyone that will listen to me.  In April of 2016, I started my podcast and started to figure out how I could best start making money online.  The income was insignificant at first. This meant I would return to the corporate world for another 20 months while I grew my business on the side the entire time.  This meant that I worked 70 hours a week. Sacrifices are required if you are serious about pulling this off.  Let’s fast forward one more time to March 13, 2018, which was only a few days before I wrote this post.  That is the day that I left my corporate job again in order to run and grow my two businesses. 

I figured that this year would provide another opportunity to break away, but the timeline was unknown.  As I reflect back on the signs that led me to this point, I can see them now with clarity.   Here are the examples that stand out to me the most:

Sign #1 – My side hustle was making more money than my main hustle

The first time that this happened, I assumed that it was just a good week.  After it started to happen regularly, I knew that I was spending most of my time in the wrong place.  I got excited about this much more quickly than my wife did though.  She had been through this once before with me and had no interest in going back to the “poor house.”  She agreed that this was certainly a “good” problem to have although this by itself was not enough.

Sign #2 – I began to lose money by being at my main hustle

For my business, there is always a piece that will come from someone who has found themselves racing against the clock with nowhere to turn.  A more clear example that I have experienced too many times to count is when another digital marketer has overcommitted to completing a project and it won’t be possible without outside help.  These jobs usually pay a lot and I have had to turn down far too many.  This has cost me thousands and it makes no sense at all for me to keep missing out.

Sign #3 – I found the intersection of passion and talent aka “my niche”

I was so close to this point many times, but something was always a bit off.  Once I figured out the supply and demand for the different areas of my business everything changed.  Remember that the line between success and failure is really thin, so one small adjustment may change everything for you.  I have tweaked my product and service offerings, price points, etc. to get it just right.  I also was willing to put significantly more time into learning the software products that are in highest demand, compared to the average person.  

Sign #4 – I started understanding the power of recurring revenue 

I have always worked hourly, by the project or even sold books at a fixed price, obviously.  When I started to receive recurring monthly commissions from my various affiliate sources a light bulb went off in my mind.  What if I could turn some of my hourly and project clients into monthly clients?  I gave this a shot and pitched a monthly retainer with no contract that has worked really well for the marketing automation side of things.  This model can be used with most businesses so really think about this one.  I knew that once my businesses expenses were covered and my team’s payroll was covered that I would continue to grow my monthly revenue with more affiliates sign-ups and with more clients.  I also knew that having more availability for projects would equal more income too.  

Sign #5 – The fear of staying in a corporate role becomes greater than the fear of leaving it 

I have been in the position where I felt like I “needed” a job for some stream of income and benefits.  I think that it is a safe assumption that most people feel this way.  Once I started having enough success on my own, I actually became fearful of missing too many opportunities and stunting the growth of my business.  Seems counterintuitive at first until it starts to become your reality.  I realize that everyone is different and this is all just my experience.  My hope is that something that I have said here will tell someone else that they need to hear to either stay put or make the leap.

Thanks for hanging out with me through some of my backstories, and through my signs that I knew it was time to blow this thing up!  See you at the top, my friends, whenever you join me there.