Want Freedom? How To Half-Ass A Risky Side Hustle.

Freedom, in 8 Half-A$$ed Steps.

Jun 19, 2024

If you have browsed many of my posts, you know that it hasn’t been very long since my I left my full-time job and transitioned away from being a traditional employee.

I’ve noticed that leaving jobs or starting new things is not unique within the Substack community. So I thought it may be worthwhile to talk about what can be one of the tougher and less glamorous parts of ditching (or taking a break from) a 9 - 5 job:

Paying the bills!

For me, real estate investment plays a key role in this whole bill paying thing. But to be clear, I don’t have a story to tell you about a fancy 7 figure net-income from some enormous real estate empire. Because for me, that doesn’t (yet 😉) exist.

But I will tell you about how doing something half-a$$ed, may not be half bad.

An 8 Step Journey

This post is a tad longer than my usuals, but I hope you’ll hang around and hear me out. I learned a lot, so maybe you’ll learn a little something too - and not just about real estate.

STEP 1: Right place-right time + taking advantage of a value-add opportunity + some luck

In 2014 I bought a house. I’d bought the home because it had great bones and sat on a gorgeous lot, but the interior was outdated and ugly so it was cheap.

The local market appreciated, I invested in a ton of improvements, and I got a massive interior renovation that was mostly paid for by my insurance company when the septic tank failed (eww).

STEP 2: Use part of the profit to buy another house, then rent it out

When I sold the house in 2021, I used some of the profits to help with a down payment and bought a new home closer to the beach.

In 2022, I went to stay with my son’s family in California for a few months. The plan was to give them a hand with baby #1 while mom was on bedrest, pregnant with baby #2.

I decided to put the beach house on some of the short term vacation rental platforms just to see what happened while I was gone. I took some photos, put up a description and went live.

To my surprise, people booked. I was kind of amazed. It seemed too easy.

That was the start of my genuine interest in real estate investing.

The Florida place - but this is a much better photo than any in that first listing.

Step 3: Learn more about investing

I started dreaming about retiring early and joined tons of groups to learn more about investing. Later in 2022 I moved to Colorado for a new job, and so resumed renting out the house in Florida.

I listened to an investment pitch from a group of realtors in Michigan at one point. I didn’t end up buying what they were selling, but in the process I learned about an off-market triplex for sale in their area. It was on a local ski hill.

It was so… cheap. At least compared to markets I was accustomed to. It seemed a little too good to be true.

Step 4: Buy more property

I recall having a chat with myself just before buying the triplex. The conversation went something like this:

To self:

Rose, you are about to buy a triplex, as in, three separate residences.

The whole property clearly needs a lot of work. How are you going to do a renovation remotely?

Plus, you’ve never even been to Michigan, let alone bought a house there.

They have snow, and basements, and heat... all things you know nothing about since every home you’ve ever owned was in Florida.

You don’t know anyone in the area except the realtor - and he has already proven that he is a slime-bag.

You have zero true real estate investing experience.

Plus, you have a full-time job - this might be too much to take on.

Are you sure this is a good idea?

Self responding to self:

Good points. This might be extremely stupid.

But there is only one way to find out, plus, I bet I’ll learn a lot more doing this than by just reading about real estate investment online.

With that settled; I bought the triplex.

The triplex, midway through exterior repairs and repainting.

Step 5: Deal with stupid decisions and spend a lot of money

The triplex needed significantly more work than the inspection had revealed or what I’d budgeted for. (This was largely due to my lack of experience in estimating based on what was shown in the inspection. Plus a certain level of denial. Plus, so much mold.) In reality, it was a full gut job: new roof, new gutters, new windows, new basement, 3 new kitchens, 6 new bathrooms, new paint, all new floors.

Eventually I realized I needed help. I couldn’t manage satellite programs plus every single detail of this massive renovation including furnishing 9 bedrooms, 3 kitchens, and 3 living rooms - by myself. I gave in and hired a designer to help.

I was burning through the remainder of the profits from that first Florida home fast.

Michigan property - the designer worked miracles (for a price).

Step 6: Run out of money

Eventually, I ran out of money. I had to start saying NO and draw the project to a close with some things unfinished. Amongst other plans that I had to let go of or delay, each of the 3 units had its own beautiful cedar hot-tub room but I just didn’t have any more money to get the hot tubs in working order. We secured the rooms, locked the doors, and moved on.

Step 7: A bunch of other challenges

If stuff could go wrong, it did. Let’s just say there was a period of time when I wondered if this was the worst financial decision of my life.

Often the only thing that kept me moving forward was me reminding myself that this is like any other hard thing and that at least for right now I needed to HOLD, HOLD, HOLD.

Step 8: Quit my job, write, travel & work on start-up projects

Somehow, with all of my mistakes and questionable decisions based on lack of experience - I now own two cash flowing properties. Or as we call it in the industry, four cash flowing doors.

This isn’t the first time I’ve taken a break from a full time job and lived off of savings, but this is different. The real estate is sustaining itself, which means it is taking care of most of the major bills - and putting a roof over my head.

The real gift here is that it massively extends the runway of time I have to work on projects before I am in any legitimate danger of running out of money. It is giving me a real chance to build something of my own to create other streams of income for a more sustainable long-term future as a non-employee. Or, to just chill for awhile before I go back, if that is what I decide to do.

The real estate is doing what I’d always hoped it would: it is buying me freedom, and options.

The Key Wasn’t Doing this Well, The Key Was Just Doing It

Honestly, I’m amazed with how this is all working out. I’m amazed because at least according to my usual bent towards trying to do things well - I really didn’t do that great of a job at any of this.

That isn’t meant to sound like some kind of false humility… Truly, my primary focus over the past few years has been on my full-time aerospace job. I was damn busy with other things while all this was going on.

As a result, I didn’t research a lot of real estate things I should have. I said yes to a lot of things I shouldn’t have. I ignored my gut a lot of times I should have listened, because I just didn’t have time to deal with it. I made many expensive mistakes.

I did work hard, spending many Saturdays and Sundays after a long work week trying to keep up with the properties. But for the scope of what I was doing, and how new it all was to me - it really wasn’t enough. If I had it all to do over there are a ton of things I’d do differently.

In essence, I half-a$$ed the whole thing.

But at the same time, I realize that if I had played it safe - it would have taken me a decade, at least, to learn as much as I learned in a few short years by diving in head first.

It is almost as if not being a perfectionist, not waiting until I knew everything-about-everything before starting …just moving forward and doing something - has paid off, in a pretty huge way.

This was a True Story of Half A$$-ing My Way to Freedom

What about you? What are you not doing because you are afraid you don’t know enough?

Is it possible that you are missing out on building your path to greater flexibility or freedom on the side because you are being too careful? Because you are too afraid? Because you think you don’t have enough time to do it as well as you’d like to?

I’m all for careful risk management and planning - but consider where you could stretch yourself to make a genuine difference in the quality of your life.

I’m here to tell you, it works and it’s worth it.

~ Rose 🌹

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