Stop working for the man and start working for yourself

9 Replies

My husband and I started our fix and flip business about two years ago. Although our pace has been somewhat slow to start, we have had great success. We are in the process of growing our business in order to start speeding up our renovations and (in theory) bring in more profits annually. My husband works for our business full time as the general contractor, while I have maintained my position with a great corporation who has been my employer for 15 years. I enjoy my job, it pays well, provides us with retirement and health benefits, as well as stability for our family. Although I am content where I am, I often find myself thinking more about working for our personal business. I really enjoy real estate and often find myself day dreaming about what it would take for me to quit this job and get into real estate full time. I have entertained the idea of getting my real estate license (so we could be saving money on our buys and sells) as well as helping take care of the odds and ends errands that eats into my husband’s time (running to stores for materials, fixtures, etc.). I am also not opposed to putting in some sweat equity into our flips, although I would not be happy doing this on a full time basis.

I know that there is no “right” answer to my question as there are so many factors to take into consideration, but I’m going to ask it anyway. My question is for those who may have previously been, or currently are in a similar situation. How did you decide for (or against) making that leap of faith to leave the corporate world and work for yourself? How did you research and evaluate those "costs" of leaving the corporate world, how did you find health insurance for you and your family, etc? 

Thank you for sharing your thoughts and opinions.

Two reasons I quit. 

First, my employer caught wind of my BP podcast interview and internally investigated if they could fire me. They could not, but drama was coming.

Second I realized I wasn’t living a life I’d be proud of. Milking an easy paycheck cause I could in a job that didn’t fulfill me. 

Real estate earned me enough to quit, but I liked the easy extra pay. Once I resigned my mind felt so clear. Years of should I shouldn’t I thought vanished and I felt a huge weight lifted. 

A secondary perk was when I quit, someone’s dream job opened up and they got it. I was holding onto something I didn’t need and keeping it from someone who really wanted it. 

You need to do this. If you don't, you'll always wonder "what if" for the rest of your life. 

Having said that, it's no picnic, and there will be times you regret quitting, but it sounds to me like you've already decided. 

Having stability is great, being happy is even better. 

I'm in the same boat... but looking somewhat long term. I've determined my qualifiers are: 

-Once my business can support taking my current salary +20% out every month. 

-Once my business can no longer grow without additional time commitment from me. 

-Once I can no longer do my current job to the best of my abilities due to time constraint. 

I'm analytical but also like to set goals. Most likely once I can cross two out of three off the list, I will sit down and make a tough decision. 

@Tiffany Foy from an Ann Arbor guy to a Columbus lady, I suggest (been self employed since 2001):

1. Start your entrepreneurial en-devour on the side first (do not give up that w2 easily)

2. Once your side hustle equals to the amount you make at your 9-5 , then consider it

3. Determine how you will have your benefits taken care of (spouse, etc)

4. Then go for it. 

In a nutshell, do not leave the 9-5 until your annual salary is replaced. 

All the best!


Originally posted by @Nick C. :

You need to do this. If you don't, you'll always wonder "what if" for the rest of your life. 

Having said that, it's no picnic, and there will be times you regret quitting, but it sounds to me like you've already decided. 

Having stability is great, being happy is even better. 

Couldn't have said it better myself... Good luck with everything!

Hi Tiffany! 

I can relate to your question -- it's the same one I thought about for a long time before making the leap early this year to leave my W2. I'm also in Columbus, and my husband & I have never flipped anything but we are into BRRRing. We started in 2014 and have 10 units now. We renovated our first property, a small 4-unit in Olde Towne East, on our own - it was a very slow process because we both work full time plus have an old dog a home that needs at least one of us to be home every evening. :) It was a great experience, though, and I definitely feel like there is a part of "us" in that building! 

I ultimately made the decision to leave my cubicle job early this year to become a real estate agent. It has been an amazing experience for me so far! I am a "people person" and the 8-5 desk life didn't suit me well, even though my job was interesting and in the real estate industry (real estate market feasibility analysis). 

I'd be happy to meet up for coffee or lunch sometime to talk about pros and cons if you'd like. Feel free to reach out if so! Either way, best of luck with everything!


If you enjoy your job there is nothing much better than benefits and a pension. I do not advise anyone to give up a job they enjoy and especially not to put all your eggs in one basket. If the real estate markets adjust in the future house flipping is going to take a major hit. Flipping only works when appreciation is on the rise.

If you care about financial security do not give up your job. It has far to many valuable benifits. You can be a real estate agent and still hold your cararer job.