The Challenges and Rewards of Being a Real Estate Investor
The Challenges and Rewards of Being a Real Estate Investor
Real estate investing will test you.
Emotionally. Financially. Mentally.
It’s not all passive income and cute front porches. It’s confusing spreadsheets, interest rate whiplash, flaky lenders, and wondering if you're crazy for considering a 1970s duplex with avocado-green tile and questionable foundation repairs.
But you know what else it is?
Freedom. Wealth. Impact. Confidence.
The pride of knowing you took a risk, ran the numbers, made a decision—and now your money is finally working harder than you are.
That’s what keeps me in the game.
That’s what makes me passionate about helping others do the same—whether it's through Kick Corporate, PRIMO, or the first-time investors we coach who just need someone to say, "You’ve got this. Make the offer.”
Let’s break down the challenges—and the rewards—of being a real estate investor.
Challenge #1: Analysis Paralysis Is Real
Let me guess—you’ve got a spreadsheet with 14 tabs.
You’re running cash flow scenarios in your sleep.
You’re watching BiggerPockets and YouTube and IG reels about everyone else’s deals...
But you still haven’t made an offer.
That’s not analysis. That’s avoidance.
I’ve had this conversation so many times—especially with folks coming out of the corporate world where every decision has to be fully baked, PowerPointed, and reviewed by a committee.
Real estate doesn’t work like that.
Here’s the truth:
You learn way more from writing an actual offer than you ever will from hypotheticals.
Because the moment you send an offer, a few things happen:
You get to test your own conviction.
You open the door to negotiation and real-world numbers.
You move from content consumer to decision maker.
And guess what? It costs $0.00 to write that offer.
No one’s charging you to take a swing.
So why not step up to the plate?
Challenge #2: Shiny Object Syndrome
STRs! MTRs! Burrs! Syndications! Subto!
Should I buy a flip in Bend or a duplex in Ohio or lend $50K to a flipper in Texas?
Sound familiar?
So many people in the investing world jump from one strategy to another, thinking the next one is the answer. (And the Instagram algorithm doesn’t help.)
But you don’t build freedom chasing every tactic.
You build it by choosing one strategy and going deep before you go wide.
The magic is in taking aligned, focused action—not chasing trends.
Challenge #3: Fear of Getting It Wrong
Look, I get it.
I was terrified when I bought my first investment property.
I’d spent years in the corporate world, used to managing billion-dollar product lines—but this was my money, my name on the loan, my risk.
But you know what changed the game?
I stopped obsessing over getting it perfect and committed to getting it going.
Because here’s the deal:
You will mess something up.
You will have a water heater flood or a tenant bounce or a budget that goes sideways.
That’s not failure—it’s feedback.
The real risk isn’t making a bad deal.
It’s staying stuck and never making any deal.
Reward #1: Your First Check That Isn’t From a Job
There’s nothing like it.
The first time a rent payment hits your bank account—or a flip closes—or your borrower sends you a wire for interest on a loan you funded from your savings, not your time... it hits different.
That’s the moment you realize:
“I can earn without trading hours for dollars.”
That is the moment you start unhooking from the corporate matrix.
Reward #2: Compound Confidence
Every deal teaches you something.
Every closed loan, every tenant placement, every renovation budget gone slightly sideways builds reps.
You start to trust your judgment.
You learn how to pivot, how to negotiate, how to ask better questions.
You start to walk a little taller in every area of your life.
Reward #3: You Create Options. And Options = Freedom.
This is what we’re really doing here.
We’re not just investing in houses.
We’re investing in the ability to:
Take a month off and travel without asking for PTO.
Say no to a toxic job.
Pay for your kid’s college in cash.
Take care of aging parents without draining your savings.
Work three days a week and spend the rest doing things that light you up.
Real estate is just the tool.