Why You Should Fail Your Way to Success


I played basketball when I was in high school. I confounded coaches and opponents alike because I consistently outperformed expectations. I didn’t look like the kind of kid who ought to be able to succeed, yet I did.


My high school coach believed in me and imparted wisdom that I’ve used to fail my way to success. One of the biggest lessons he shared with me was a life-changing acknowledgement: failure is our default position. People get really good at it and won’t make significant changes until the pain of languishing in mediocrity is exceeded by a burning desire to do something about it.

I’ve adjusted this philosophy through the years and tweaked it for my real estate clients when I realized how applicable his advice can be to real estate pros.

In this article, I’m going to share a solid path that can get you out of the muck and the more of mediocrity and put you on the path to personal and financial prosperity.

Let’s get started!

Close your eyes for a minute. Imagine yourself a year from now. Your career confidence is at an all-time high. You’ve closed more transactions than you thought was possible. Other real estate agents look at you with admiration. Your career outlook, health and wealth are at all-time highs.

And your family life? It’s never been better. In short, your life is firing on all cylinders. You’re shocked and amazed that you’ve come so far in a single calendar year.

The question is, how did you do it?

Now, open your eyes again. Don’t like what you see or think there’s room for improvement? Then keep reading. Up ‘til now, you’ve been failing to one degree or another. Let’s change this. I’m giving you the tools you need to make next year your best year ever. Here’s a simple checklist you can follow to make sure the you you see in a year is a you you’ll be proud to be seen.

Now is the Time to Plan Your Future

I work with lots of real estate agents. Some are thriving, thrilled to be winning the game of life and business. They get up every morning with a sense of urgency, filled to overflowing with the belief that what they’re doing at any given moment is the best possible use of their time.


Others approach every coming day with dread, with the dawning certainty that the other shoe will soon drop. They worry about health, relationships or finances and hunker down, waiting for the approaching storm to devastate them and what they’ve built.

After thousands of coaching calls and private conversations with real estate pros, I’m more convinced than ever before that there’s no time like the present to plan your future. Aren’t planning yet? Then you’re going all-in on failure. Remember, our default position is failure, not success.

Without Your Health You’re a Shell of the Person You Could Be

The nature of real estate places huge demands on your time. As a result, many of the real estate pros I talk with skip meals, grab quick, unhealthy snacks from convenience stores or a heart attack in a sack from the nearest drive-through restaurant. Here’s how to put a laser focus on your health that will give you the energy and stamina you need to make it through the day:

Weigh in regularly– The scale tells the tale. A few extra pounds are easy enough to hide – at first. Because we’re creatures of habit, we tend to continue in the direction we’re moving unless acted on by an outside force. I weigh in daily because I want immediate feedback about how I did the previous day. I want to nip problems in the bud before they become habitual. This morning routine works.

Get on a first name basis with your doctor, trainer and nutritionist – Between prospecting, presentations and closings, it can be hard to find the time to get enough exercise to maintain a healthy lifestyle. At a bare minimum, get on a first-name basis with your doctor so you can immediately address issues before they become significant challenges to your health. A personal trainer can put you on the path to better health by making you accountable. And a nutritionist is a nice bonus because you’ll get real-world advice about healthy eating plans that take all factors into consideration.


Eat right– Groceries are filled to overflowing with food. Unfortunately, much of it won’t do a lot for you unless you buy things that will help you fuel a healthy lifestyle. This is one of the reasons I think every real estate pro needs to tap into the hard skills a good nutritionist brings to the table (and to avoid the prepackaged timesavers that do little more than hasten a visit from the grim reaper).

Practice smart supplementation– The changing nature of agriculture and mass food production means that we no longer get all the nutrients we need from our food. Whether you’re a devotee of an organic, free-range lifestyle or not, the scientific evidence seems to support the idea that we need supplementation for better health. Find out what supplements will help you the most, then take them  – daily.

Getting Your Money Right (Now)

Just as you go to the doctor periodically to make sure your health is in order, you should give yourself regular personal and professional checkups. Here’s what I recommend:

Evaluate your career satisfaction– When you look in the mirror, how do you feel about your career? Are you reaching all of your goals or are you struggling? If you’re honest with yourself, there’s a pretty good chance you have work to do. If you aren’t satisfied, now is the time to do something about it.


Be a marketing magician– Too many real estate pros screw their marketing up. It’s not necessarily that they tap into too many marketing channels (although this is often the case). You should become a marketing magician. The best way I know to do this is to laser focus your efforts on dominating a single channel before expanding to others. If you don’t, you’re wasting valuable marketing dollars on expeditions to nowhere. And above all else, never, ever spend money on a marketing idea you can’t track. Your money should never go into a black hole!

Check in with your broker or team leader for a much-needed checkup– Depending on your working arrangement, you may or may not have many interactions with your broker or team leader. Make a point to schedule an appointment. Make sure you’re on the same page and that you both share the same vision for your future. Your broker or team leader should be an incredible resource who can help you unleash your real estate talents in ways that benefit you and the company you work with. If not, maybe you should reevaluate the working relationship.

Manage your production cycles– One of the most common flaws I see in struggling real estate pros is a near total shutdown in November and December. This is especially true of younger agents, though this is a trap that sometimes ensnares experienced agents who ought to know better. Keep score with everything you do. If you’re marketing yourself, prospecting, giving listing presentations, and actually doing the things which lead to success all year long – even in November and January – your Decembers and Januarys are more likely to also include a fair number of closings.

Rainmaker real estate agents have the uncanny ability to have closings scheduled… all the time.

Even a rainmaker plans for drought– Rainmaker real estate agents have the uncanny ability to have closings scheduled… all the time. The ones I work with tend to approach their work with passion, diligence and focus… and by planning for drought. They set ample funds aside to meet all of their financial obligations so they’re prepared when the inevitable dry spells happen. This does two things:

  1. It gives you an empowering sense of security in knowing that you aren’t dependent on any deal to meet your expenses.
  2. You’ll be prepared for most, if not all, of the little financial emergencies that happen (while at the same time keep you from being one of those Americans who can’t meet financial emergencies immediately).

Make Time for Family and other things that matter

I’ve talked with quite a few real estate agents who have reached the pinnacle of success in their careers, yet fail spectacularly in their personal lives. It’s easy enough to pin the blame on the job – based on raw, honest client feedback about their own relationships – here’s their version of reality: real estate has never broken a relationship that wasn’t already badly bent. An already damaged relationship deteriorates unless acted on by an outside force.


To avoid the same relationship pitfalls, it’s vital that you make family relationships and other things that matter a priority in your life. This goes for spousal/significant other relationships, your relationship with your children, as well as volunteerism and spirituality (however you define it).

Failure is Good Until It Isn’t Enough

My high school basketball coach was a devotee of failure. Not for failure’s sake but as an effective vehicle for getting and doing better. Whether you’re struggling in some or all of the above categories or you feel that you’ve done pretty well on all fronts, the reality is there is always room for improvement.

You’re squarely on a path to a destination to somewhere. Staring straight ahead, it’s also plain to see that you’re coming to a crossroads of sorts now. The path you’re on veers a little off to the left; the other curves sharply to the right. You know the path you’re on. If you keep doing what you’ve been doing, you’ll keep getting what you’ve been getting. The situation I laid out for you above leads t o the right – more satisfaction, health and prosperity.

The question is, which direction will you go?

Pick your path carefully. A lot is riding on what you do over the next few weeks.

Will you settle for more of the same? Or are you willing to embrace the idea that the person you’ll be a year from now will be the product of your next steps?

Ken SpeegleKen Speegle is Realty ToolKit’s resident real estate industry expert. Every week he writes insightful, in-depth articles about topics related to real estate marketing, each designed to help make you a better, more profitable real estate professional. Ken is the founder of therealestatewriter.com and has been a real estate copywriter since 1994.