Time to go Full time Investing?

Question

My W-2 is in a small health care setting where I am basically a social worker. Recently 2 of our 8 clients have presented with a permanent life long incurable health condition that is contagious but if you are fairly obsessive about hygiene such as avoiding Contact and hand washing you will not contract it.

Now that the second client has been diagnosed I am 95% certain it’s time to retire from this position and go to real estate full time. I was planning to do this in May of 2026 when I turn 50 but I think the time is right.

How many people took the jump to doing real estate full time before they thought they were “completely ready”, and how did it work out?

Alecia Loveless · Answer

Thank you for responding. I ran my own business for 24 years and only started working the W-2 to get the benefit of the paid for health insurance because mine had increased to $1400 a month for me and my partner. Once I started my job it never went above $350/month for the two of us again.

At the time I thought having a job would be a nice change from being my own boss and having all the stresses that went along with that, but quickly realized that I missed the freedoms of being self employed terribly.

Don Konipol · Answer

No one’s ever fully ready to give up monthly income with almost certainty for the financial uncertainty of owning a business - especially a start up business that depends not on systems with an established protocol and work of established employees but one that depends on your personal “deal making” ability, analytical skills, and dedication.

The totally risk averse among us would NEVER even consider giving up the steady paycheck, or investing in anything so risking as a business startup.  They/‘ll comfort themselves with the statistics that 7 out of 10 new businesses fail in the first year; knowing that their decision to bypass the opportunity to “go for it” is the only one that makes sense from a personal “pain vs gain” equation.  They know deep down that the pain of failure far exceeds the pleasure of success - for themselves.

The opposite side (where I personally reside) couldn’t imagine having a traditional “job”.  We may have had a “job” right out of college, in order to become familiar with the “real” work world, and or to accumulate a “grub stake”.  As soon as an opportunity for an equity (ownership) position presented itself, we jumped on it, forgoing any salary, steady income, or lifeline.  Failure didn’t deter us, but instead spurred us on.  Those of us who chose real estate investing as our business vehicle, still get “high” from successfully concluding a “deal”.  The thought of ever having to work a traditional “job” is what we fear most.

The third category, where I suspect about 50% of the population reside, and which you appear to be a part of, can happily work a traditional job IF they enjoy the work, like the people they work with, have room to improve their skills and have opportunity for advancement, and IF they are being adequately compensated.  However, in back of their mind they always feel the allure of independent employment, whether that means owning a traditional business model or being an independent contractor or a full time real estate investor.

In many way you as a member of the third group have a better handle on the risk reward than members of the first two groups.  The first group is too afraid of failure to be able to take advantage of business opportunities, the second group is too afraid of having to “take a job” to pass on opportunities they should pass on.  IMO, you have reached a moment when you are not getting the satisfaction from your job that you desire.  If you LOVE operating in the real estate field, then go for it - it WILL all work out.  You already have more knowledge and experience than 95% of real estate investors, what you don’t know you will learn on the fly.  If you want to do this with a safety net, then become a real estate broker and broker commercial deals “on the side”, while maintaining your investment program as your main focus.

Good luck.  My gut feel is that you will do VERY WELL.

Steve Vaughan · Answer

I did it 21 years ago at 31.

No way I thought I was completely ready.  Had a wife and baby to boot.

It worked out great and I had only book knowledge, not experience like you have.

Your work situation sounds like a gift-wrapped opportunity in disguise. I say go for it!