When Is It Time To Go From Side Hustle To Full Time Entrepreneur?

I’ve wanted to be my own boss since I was 5-years-old. My dad did it, my grandfather did it and gosh darn it I was going to do it! I’m 29 now and August is my very first month as a full time entrepreneur.

Pause for my happy chair dance.

I’ve been side hustling the shit out of life since I graduated college, trying to build my dream, brick by painstakingly slow brick, toiling away at soul sucking customer service jobs to pay the bills all in the name of making the big jump from side hustle to full time business. I am not a patient person but I am a planner and I prefer calculated risk to blind, free falling jumps into the abyss so I continuously asked myself WHEN is the right time to go for it?

On the one hand, going all out and all in is no joke and there are a lot of factors to consider so having a plan sounds great. On the other hand freedom, fulfillment and your dreams await you so it can be enticing to just say f*ck it, I’m jumping (this option always looks especially good when your manager gets on your nerves). The thing about a dream that you’ve been working toward since you were five is you REALLY want it to work out and turn into a long lasting reality, so I recommend going with a plan.

First things first, you’ve got to figure out what you’re actually going to entrepreneu (yes, I made entrepreneur into a verb). This can take more time than you might think. I tried on quite a few hats before I landed on graphic designer/brand storyteller. This trial and error phase might feel like a lot of “failure”, I definitely had to weed my mind garden of thoughts like “This is something you’ve wanted since you were little so you should’ve been able to make that idea work!” Yikes. Just typing that on the page makes me cringe. So be a badass mind gardener and have grace for yourself because every idea that doesn’t work out will teach you important lessons and skills that will help you nail the idea that does work.

Once you’ve found your zone of genius and how to monetize it, it’s time for the planning stage.

The before I quit list

Lists are great. They keep you focused on what’s important and help you build a parachute for the jump. I just found out (according to my Human Design) that I personally create lists so that I can 1. Appear really busy (eye roll because it’s true) and 2. Because I love the feeling of checking a box. Since I love lists, I naturally made one that would ideally have every box checked before I went full time biz owner.

Spoiler Alert: I didn’t end up checking all the boxes and the house didn’t catch on fire (much to my surprise).

Everyone’s list is going to look different. I had things like…

  • Write out my social media strategy
  • Schedule an accountability meeting with Dad once a week
  • Buy a phone that doesn’t malfunction

Figure out what’s important for you to put into place before you quit your day job and write it down where you can see it everyday. 

A word of warning, this list can become an excuse NOT to jump. More and more things get added to the list because we need to feel just a little more certain about this decision until we wake up 10 years later and realize we never took the leap. Let it keep you focused but don’t let it hold you back.

The piggy bank

Putting a ton of financial pressure on your newborn baby business before you and it are ready can be paralyzing. You will also likely be moving from a guaranteed paycheck to an income that solely relies on you. For me, having a certain amount in my savings account before I quit my day job was important to mitigate this stress. If I had a slow month, I would still have money to pay for my basic needs.

Your number will be unique to you. Some things to consider are your monthly living expenses, your business expenses and always add in a cushion of at least 15%.

Pro Tip: Want to get to your savings goal faster? In addition to your monthly contributions from your paycheck, set up an app like Qapital, which rounds up purchases to the nearest $ and deposits that extra bit into a savings account. You can also Marie Kondo your life and sell any clothes that don’t spark joy on Poshmark.

That sets up my next piece of advice quite nicely…

Pair down your life

Audit every area that you spend money. What are the essentials you need to live and where can you simplify? Have you been eyeing a new car? Maybe stick with the one you have so you don’t take on a car payment until you’re more established. Are you paying for a two bedroom apartment when a one bedroom would suffice? Are there any subscriptions you can let go of? Having the least amount of financial obligations possible will alleviate the financial strain on your new business. 

Build your support circle

You can’t do this alone! Gather the people who are always in your corner and keep them close to you. Be selective about who’s in this group. At first my dad (even though he was my inspiration) was more comfortable with me getting a “normal” 9-5 so he wasn’t the one I went to for support with my business. He’s since come around and now is my go-to for financial and operational questions, but it took time. 

Do you have friends that are also starting their own businesses or trying to transition their side hustles into full time gigs? They will understand what you’re going through. Do you have a mentor that has already been through this and can offer wisdom when you need it? Do you need to see a therapist to manage the emotional strain a risk like this can cause? Whomever you need by your side call them in and let them know HOW they can support you. 

Last but definitely not least…

Plans change

As my coach, Kelleen Griffin, always reminds me, “No plan survives contact.” Life is going to throw you curve balls, all of your boxes won’t be checked AND you will never be 100% ready to make the jump. Build yourself the best parachute you can but remember to use it!

Life basically pushed me out of the plane. I worked at the same gym as my partner for my day job while building up graphic design on the side. I had it in my head that I would quit in a few months when I felt “ready”. One day (way before I was “ready” for the jump), out of the blue my partner came home and said he was unhappy. I moved out and put in my two weeks at the gym the next day. Not quite how I had imagined it in my head but it was the shove I needed to get out of planning mode and into doing mode. 

Pro Tip: If getting a business coach is on your “Before I Quit List”, Kelleen is phenomenal. 

In the end, this is simply my experience so use it as a guideline not a list of rules. Hopefully it will spark your own journey to entrepreneurship, whatever that looks like for you! 

Fun Fact: There is an entire book written on this subject literally called “When to Jump” if you need a bigger parachute.


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