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My new flipping houses career


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By now, many of you may have noticed that my Instagram looks a bit different. I’m a licensed real estate agent! I flipped my first home and am already onto the second! I’m going ALL IN!

And while it may feel to some like a quick transition and that I’m off to the races, I've actually been contemplating a new career path for nearly four years. If this is familiar to you and what you've been feeling lately, here's how I finally arrived on what I wanted my “second act” to look like.

What I do when I don’t know the next step

I’d like to say that back in February 2019, when I quit my then full-time job in a fit of rage, I had a larger plan. But I didn’t. And maybe I said some things at the time about why I left (I honestly can’t remember), but I just knew what I was doing in marketing wasn’t it.

The problem was – I already knew I didn’t want to spend my life as a full-time blogger; it’s why I quit entrepreneurship and went back to a full-time job. But, I was pretty irritated with the leadership at my old job, so I quit because I knew I had blogging as a side hustle to fall back on.

(Yes, I realize this makes me one lucky duck. I will always be grateful for this blog and the opportunities and safety net it has provided for me for over eight years now.)

After I left that job, I was so confused about what I wanted and who I wanted to be. 

So, I decided to do what I always do when I’m befuddled and that is to sit, be quiet, and listen. When I do this, I always hope my heart and intuition will clue me into the next step.

All of this happened in February 2019, a full six months before I got pregnant (another happy accident.) And when I began to struggle with morning sickness/hyperemesis…. weeks turned into months.

By the time my morning sickness passed at week 16, I’d basically been out of “work mode” for six months. And rather than kick myself and try to “make up for lost time,” I decided to lean into what I was feeling – which was tired, burnt out, and as uncreative as I’ve ever felt. (Pregnancy brain, anyone?)

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Why flipping houses?

Battling the guilt was hard, but honestly, taking a step back from the “hustle” was one of the most needed things I’ve ever “gifted” myself. Here's what I did during that time. Instead of working I……….

  1. Reflected. During my year off I had a lot of time to think: about what I wanted to spend my life doing, how I wanted my life to look after our son was born, and about what really made me happy.
  • Started with what I didn’t want. As an entrepreneur, I’m always excited about new ideas. With so many enticing options and opportunities, it can be hard to choose the right next step. I mean, if you can have ANY DESSERT IN THE WORLD, how do you choose? For me, it was helpful to make a list of what I didn’t want. When faced with the prospect of something new, I could look at this list, and it kept me from going down a lot of rabbit holes.
  • Trusted.  Oooh, this is a toughie, because anxiety can get in the way of so much in our lives. It was f*cking frustrating at times to sit on the couch and think about what I was going to do with my life and come up with a blank each time. But in those moments I had to assure myself that what the universe meant for me would make its way to me. So, when Soapbox and I began talking in the Fall of last year, and they acquired this site, I knew it was meant to be. Even though I didn’t know what my next career would be, because I knew what I didn’t want, I was able to attract a new owner for this site, which freed me up to go and find out what that next “thing” was.

My new flipping houses career – how I did it

Fast forward to February 2020 and a year has gone by and I wake up one morning, more motivated than I’d been in 12 months. A voice told me, “Go get your real estate license, you won’t have time once the baby arrives.”

So, I signed up that day and two weeks later I was in class eight hours a day. I’d always wanted to get my real estate license, ever since I wrote a book about millennial homeownership back in 2016 (!!!!), and I figured if the RE thing didn’t work out, at least I could cross it off my list with no regrets.

I’m glad I did it because finding time to take 60 hours of class would be really hard with the baby. And as it turns out, my hunch was right, and I love real estate and am fully obsessed.

Here's an overview on how I find good houses to flip and another great resource on how to find houses to flip. Here's my guide on how to flip houses if you have no money to start with.

How to fund a second act

I realize that I am writing this essay from a place of complete privilege. Not everyone has a business they can put on autopilot for a year while they figure their shit out. So many people have to show up for work each day and it can be hard to take time for yourself on top of the day-to-day grind: work, self-care, family obligations, bills, playtime.

But through sound financial habits, I was able to give myself one less thing to worry about while I took the time, and that’s the money. I didn’t have to worry about that.

And also, by creating a business of my own, I had something to sell in order to gather the necessary funds to start real estate investing. There are definitely many advantages to working for someone else (Insurance, retirement benefits, for one.)

The TL : DR

The whole real estate thing came about because I finally felt unafraid to pursue this passion of mine. I'm getting older – it is NOW OR NEVER. And in looking back, I realize this passion didn't just appear from nowhere: it's been riding alongside me this entire time. For many years it was one thing or another that kept me away, but giving myself time to think through this transition and to tune into my own voice has allowed me to confidently choose rather than be confused by how much noise is often in our lives.

Now I realize that giving yourself time and space is NEVER a waste. Even if others seem to be charging ahead of you, even if you feel like you’re getting left behind. So, that’s really what I want to impart with this essay: things take time. It's okay to go on autopilot whenever you need to. And it is definitely more than okay to unsubscribe to hustle culture. It's okay to rest.

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