My Achilles Heel

by Dan Gheesling

In January of 2015 I did not post a single blog.

I didn’t write a single article, and I didn’t write, or share my goals for the new year.


Because for the past month I have just put my head down and got to work.

A lot has changed in my businesses and I have spent a lot of time working on my offline business, which has always been real estate.

I wanted to write, but this article kept popping up in my head from one of my favorite business thought leaders, Gary Vaynerchuk.

The gist of the article basically says: just shut up and get to work.

For many reasons, that article has resonated with me for a very long time. When I look back at the things I’ve done, I’m not satisfied.

From a business standpoint, I’ve always wanted three things: to create multiple passive businesses, to continue to invest in Real Estate assets, and have a creative outlet (YouTube & Twitch) that can be monetized.

In business that’s all I want and need, but it is not always what I have focused my time on, until now.

Of course, there is more to life than just business – we all have a reason for “why” we work so hard.

For me, it’s for my family, and the ability to free up time to do other things I love that have nothing to do with business or money, but are more about helping others (i.e.- coaching football).

The catch 22 is that you can’t do those things that you love to do, without a business behind you. It’s a tough balance for a lot of people who work for themselves, myself included.

My Achilles Heel

One of my biggest downfalls (and motivators) is that I am extremely hard on myself.

Rarely, if ever, do I look back at what I’ve done in a day, week, or even month. I always look at what I didn’t get done, or how I could have gotten more done, which is extremely damaging over time.

Finding the balance of staying driven without resting on your laurels is freaking hard, at least for me it has been.

It’s the Bane to my Bruce Wayne, and my ultimate Achilles heel, and if you’re the same way, you have to identify it and address it.

There are a few tips you can use to help yourself (I picked up the 5 Minute Journal and highly recommend it), but the only thing that really works to correct you being-to-hard-on-yourself syndrome is to hit the pillow hard.

The days you work so hard on your business/family/whatever you love, that’s when you hit the pillow at night.  You crash incredibly hard because you have worked your tail off all day on what is most important to you.

I’m not going to sit here and tell you that I’m a master at it, because I’m not. I have off struggle days , and days where I don’t get anything done. But, if you put your head down and work, things will get better… they have to.

What I Got Done

Over the past month, here’s what I’ve been able to get done:

  • Created and executed a marketing plan to acquire private real estate deals
  • Closed 3 deals (Goal was 4 – not good enough)
  • Delivered a Leadership Presentation at Grand Valley State University


DAN GHEESLING!!! @dangheesling What an awesome guy. Really great speech. #BigBrother #BBLegend #GVSU

A photo posted by Jake Jager (@jager_meistro) on

  • Formed a mastermind group
  • Took a mobile game concept from idea to 30% complete with a new partner (more on this in future)
  • Completed a 30 day pushup and plank challenge
  • Published 2 episodes per day on my YouTube gaming channel
  • Posted high quality dad joke on Snapchat (username: dangheesling) for 30 straight days

So What?

Even while I was writing this out, I had to catch myself saying “dude, you didn’t get that much done in January.” And it’s true to some extent, it’s a good start to 2015, but it’s not enough, and even if it was enough, it still wouldn’t be enough.

But that’s the pivot, or change in this blog moving forward.

I’m going to be sharing with you, physical actions I’ve been taking, what has been working, and what hasn’t, in business, my gaming channel, and even life – with the goal in mind that you can learn or take something away from these posts.

Whether it is motivation to get started on something, learning from something I failed at, or even sharing one of your own wins in the comments, I’m glad you’re here.

The blog isn’t going to fit into some easy to categorize niche, like “business” or “motivation” – because when you break down everything I do, from speaking, to writing, to real estate, to how to get on reality TV, to gaming, to coaching, none of it fits in a standard check box, but for me it all works… sometimes. :)

Thanks for taking the time out to read this post – if you have 30 seconds, I’d appreciate if you let me know one thing you liked about this post, and one thing you disliked!

  • Miranda Wiley

    I like that, so far, everything you have blogged about fits into my life in some way. I totally get this post. What I don’t like about this is you’re younger than I am and have your stuff way more together than I do. Lol. Keep up the great works!

    • Dan Gheesling

      Ah no worries Miranda, we all do things at our own pace!

  • Colleen Kelly

    Well, I like the sound of your idea for the blog. I think a lot of people will be able to identify with you, your posts, and find a few answers for themselves along the way! :) The blog has always seemed to speak to something going on in my life. The blog has always been one of my favorite things you have chosen to do, ever since the “IwouldCoach” days. What I don’t like, okay, that you are too hard on yourself. But, that would be calling the kettle black. lol I do it too. So, I think I may learn a few things too! I always have though. :)

    Thanks for taking the time to write and post this Dan! :) I really have always enjoyed your posts! :)A push up and plank challenge huh ? WTG!! :D Planking can be tough! Good job! :)

  • Laura Dyas

    Dan, your blogs are interesting and of value to those who are seeking to improve their organizational skills and personal skills. You have a definite way with words that brings the reader to conclusions in a well defined manner. Your blogs are well written and easy to read. The only suggestion I would make would be to provide the reader with some tips possibly at the end of the blog as a way to tie back to the topic. For those who are looking to move away from perfectionism and to find balance in life, those tips would be incredibly helpful. As always, your work touches so many lives and you and Chelsea are doing amazing things to make a real difference in the world. Keep up the great work Dan and thank you for all you are doing. You had a real choice when you won Big Brother, you could have simply walked away been someone no one remembered. Rather, you decided to help others. For that, you will be remembered as someone who is making a real imprint in the world.

    • Dan Gheesling

      Hey Laura, thanks for reading and the kind words. Great suggestion, I’ll use that in my next post!

  • Jennifer Lee Healy

    What I like about this post and everything you write, is that you are so straight from your heart in everything you write…you are real and honest, and inspirational and motivational with every word. That being said, although you have realized and addressed improving it, what I didn’t like is how much you down on yourself…you truly have inspired many and you do everyday, so give yourself credit everyday knowing that even if you are not speaking at that moment, your past words and actions reside with your fans and you are always giving even when you are not trying. I have no doubt, that you will accomplish all your goals…you have more drive and commitment than most! #KeepWriting #KeepInspiring

  • Kelly Authier

    I enjoy reading your posts because you are real and honest. This post was no exception. It sounds like you’ve done a lot this month! I am the same way when it comes to accomplishments: I tend to downplay them and think of what I didn’t do. We are our own worst enemy.
    You are truly an inspiration because you are constantly striving to do better. The only thing I would recommend is for you to give us more detail on how you focus your energy. Are there specific tips that you can pass along?

    I love reading your blog and receiving your emails because they motivate me to do better and to be better.
    Thank you so much for that!

    • Dan Gheesling

      Hey Kelly – thanks for reading. I can share that in a future post!

  • AthenaSantana

    Hey Dan!
    For starters, I’m really glad you’re still blogging because I didn’t think you were still doing it. Sorry. Lol .:-) I have always enjoyed reading you’re blogs, I always learn so much from them, and make an effort to use what I have learned. :) it helps me so much, so thank you for that. :) the thing I don’t like is that you feel you haven’t done enough, you sir, have done so much and you should be proud cause I know I am. :) thank you again for posting. :-)

    • Dan Gheesling


  • Connie

    DAN!! Beating yourself up for “not doing enough” won’t get you anywhere. Life is like climbing a mountain. Sometimes you look ahead and think you have so far to go and so much to do to get to the top. Sometimes, you have to stop, turn around and look at how far you have come and how much you have done – that is what will motivate you to keep going! Stay positive my friend. You have changed so many people’s lives – all in a good way! Keep up the good work!!

    • Dan Gheesling

      Thanks Connie!

  • Craftible

    Awesome read, I love when you post things of this nature, it makes me want to follow what you do almost as similar as possible, thanks for motivating me to want to do even more than what I think I can do.

    • Dan Gheesling

      Thanks for reading Craft.

  • Jessica

    I’m a singer-songwriter and I’m from Omaha Nebraska. You are really good at saying kind and encouraging words. I always get worked up about my music not being good enough, and I always compare myself to other people. Have you ever felt this way before? I know that you’ve had a lot of success in being in the ultimate big brother player! I’m going to start performing with a tour for young children (girls) and I want to empower and life them up, and inspire them. I know this isn’t your strong suit, but if you have any advice of how to get more girls to buy my merchandise, that would be great! My album is called Won’t be Defined, and you can see my website is call Any advice would be amazing! My youtube is jessie11200. (There’s a few free songs on my website that are on my album)

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