Is Getting to Six Figures Largely about Overcoming Psychological Challenges?

Is Getting to Six Figures Largely about Overcoming Psychological Challenges? post image

I was watching basketball videos on Youtube the other day and was struck by this documentary of Lebron James’ high school team. In their junior year, they choked and lost to an inferior team in the Ohio state championship. A few things struck me about the way they failed.

First, they did not expect to be challenged emotionally– they didn’t have a process in place for when things got bad. At a critical moment, the point guard suffered a complete melt-down and launched the ball in frustration and received a technical foul– essentially icing the game.

Second, the way the coach attempted to address emotional challenges at halftime (in a subsequent challenging game) gave me the impression that he was equally unprepared. He resorted to one of those “this is your one chance” movie type speeches. I couldn’t help thinking– isn’t this guy just fanning the fire? If these kids are frustrated and confused, does it really help to raise the stakes? (btw, Andre Agassi covers psychological challenges in sports beautifully in his excellent biography, Open).

The same type of emotional failures are what are holding many of us back from the type of business success we’d like to see. The difference in sports? There’s a scoreboard. It’s easy to know what “failure” is and re-calibrate. In our own lives and businesses, we tend to move the goal when the going gets tough (I am no stranger to this sort of rigging the game for emotional security).

At the early stages of my career I tended to think it was ideas and opportunities that were holding me back, not mindset. It was the world, not me. My opinion gradually has changed. It’s not opportunities that are rare. It’s the ability to see, define, and execute on them.

I jotted a similar idea at the end of the 2012 summer, one in which I spent many weeks helping (or trying to help) other entrepreneurs.

“Getting to six figures is largely about overcoming psychological challenges, getting to seven is largely about strategic challenges.” 

This could partly explain why those with at least 6 figure businesses make such remarkably better clients– you aren’t dealing with whims so much as you are dealing with systems (of course, you are always dealing with a little bit of both!).

Here’s a few sketches of emotional roadblocks that aspiring entrepreneurs face, and perhaps, what to do about them (I’ve been guilty of all these, perhaps these characters are actually small devils in my personality).

“Good idea Glen” is overly attached to his idea.

Who knows why people get so attached to a general idea of something that doesn’t exist, to the detriment of a very clear and simple ambition. Why do people get obsessed about creating [insert great idea] at the expense of creating a life of financial abundance? I can think of many reasons of course, but I feel that often those without much entrepreneurial experience over-attach themselves to their unborn ideas and don’t properly see what they cost to hold on to.

How many friends do you know who’s great idea is more like a great boulder in the mountain pass? And perhaps it’s a cultural thing too— we lionize this sort of individual creative vision, so perhaps even “having a great idea” is some sort of consolation.

Potential solution? Prioritize great engagements over great ideas. If you can, put it to bed for a few years and circle back.

Give up Gavin has no grit.

I still remember the morning when I wrote the “1,000 Day Rule.” That article fell right out of me. Honestly, it takes me forever to write, but that thing just cascaded right off my fingers. I can remember so many times, and hell, most of 2009, where I just wasn’t sure if I was going to make it. I had no idea if my business was going to implode on my head. That’s my life! A washed up cat furniture salesman!

That article captures some of those emotions I felt. Like waking up and feeling something more or less like “ah fuck, this again.”

What’s required to make an income from running a company online isn’t rocket science. I mean, here I am! Often it’s those with a stubborn bull-like persona that are able to just keep plowin’ despite the often daily and niggling emotional turmoil being an entrepreneur can be.

Potential solution: If you are human, you’ll probably regularly want to give up. Not doing so is the only thing standing between you and the type of business success you are seeking. (Hey Lebron even gave up a few times!) Wanting to give up is normal– having a process for dealing with it isn’t. For me this is having systems of “reset” and accountability. Consider committing to a business or accountability partner, start building a tight professional network, make commitments and make yourself accountable. Re-frame, and re-energize. Remember that the daily emotional turmoil you’ll face in your first 1,000 days is nothing compared to the more subtle, settled, and consistent turmoil of having never faced and overcome the challenge at all.

No fun Phil thinks everything is a drag. 

We’ve probably all been in one of those torturous conversations where the person who solicited advice about what they supposedly want to do is turning it all down, more or less saying “yeah, but I don’t want to do it that way” and so on. There’s a theme I see with people who are able to go out there and make it happen– they think (crazily!) that it’s actually going to be fun. With a gleam in their eye they are willing to commit to a crazy goal. “I’m gonna go make a million bucks.” Or “I’m going to build a new app by end of business every Friday and try to get users for it.” The clearer the better. If your idea or business doesn’t harness your joy, your fun, your sense of misbhavior, perhaps it’s worth asking yourself the more fundamental question. What is it that you are doing this for? 

Potential solution: why is it so hard to say something specific, fun, and profitable? Not sure on this one…

I’ve got a huge inventory of emotional problems :) (Non-falsifiable Fanny, Me Me Mike, Weary Wayne… it could even be an ebook:  Good idea Glen and His Ugly Cousins!) 

Curious if you are seeing common patterns holding you or others back? Is getting to six figures largely an emotional challenge? Also love any heads up on good basketball videos! That’s “procrastinating Pete.”



Published on 07.22.14
  • Adrijus Guscia

    More of those awesome names please! Would be useful to see the list of all of those ‘persons’!

    Feeding Procrastinating Pete:

    P.S What other sports vids you watch/books that you read? Agassi’s on the wishlist now. Been always a fan of bodybuilder docus/books (and not douchebags from the average guys but the pros).

  • Josh

    I resonate a lot with this message.

    Profitable ideas are easy enough to come by. All of the information one needs about how to build a business is out there. The issue isn’t of what or how, it’s me. 

    I’ve seen a lot if opportunities pass me by that I didn’t take advantage of because I wasn’t right in the head.

    Those failures made me ask why I wasn’t able to capitalize on them while others who were less skilled or not as well positioned were about to.

    It comes down to courage and consistency. Until I’m willing to step into the ring with the marketplace and get a bloody nose every day, success will continue to elude me. 

  • Spot on. Getting to 10k a month is the hardest thing. You’re validating the idea, building the process and overcoming your own demons. Once you get to that point, it’s easier to scale.

    I would also add that if you do it once, you can do it again. It’s not magic, usually just involves a lot of late nights, starting over, and taking lots and lots of CILTEP.

    See what I did there at the end ;)

  • Adrijus Guscia Thank you for sharing this video.
    Along with this article and this video, its the boost I needed to push myself! Inspire myself to do better and hit my goals and beyond my goals.

    Thanks you guys.

  • Ricardo P Aquino

    Another awesome post. I’m a big believer that adversity builds character. However, having processes in place for when it gets tough is incredibly valuable.

    Thank you!

    Favorite basketball player of all time?

  • Just curious, Dan, how far through the 1000 days were you at the time you wrote the 1000 days post?

    Really like the idea of having systems to handle it when you want to give up. In addition to being in a mastermind, another thing I do is to compare where I am now to where I was a year ago. Entrepreneurs are often so forward-thinking that we fail to look back, and often undervalue the shitload of stuff we’ve accomplished in the past year.

    When I take time to reflect on this, it motivates me to keep going because heck, if I’ve done this much in the past year, what awesome things could I accomplish in this next year?! (Also a litmus test – if you look back and discover you’ve been completely stuck or stalled for the past year, then you’re doing it wrong – pivot or change needed).

    As for what’s holding me back? Nothing, I’m steadily plodding towards six figures. There are things I could do to get there faster, which I’m unwilling to do. This might sound like No fun Phil saying “yeah but I don’t want to do it that way,” but for me it’s about work/life balance and enjoying the work I choose to do.

    I’d rather take 4 years to reach six figs and enjoy the process and result, than reach six figs in six months and be overworked, or having built a business or job for myself that I don’t enjoy.

  • Adrijus Guscia

    Ugh… I’d be careful with saying nothing is holding me back… I’d never say that, there’s always some mental block that is in my way and I don’t see it.

  • haha very nice !!! you are right about the once done, second done as well, probably speaking equally to the issue of mental barriers being the primary ones…. i mean, there’s a lot of abundance out there, it’s the seeing it that’s the critical part. and of course, the supplements.

  • great vid Adrijus…. Kobe has such an incredible reputation for work.

    Pete thanks you.

    I love watching all kinds of sports vids on the web. Arnold’s book on weight training is good, Mike Tyson’s recent book is so very good (but more about his lifestyle than training mindset), the Linsanity documentary was really cool and inspiring.

  • yeah yah know you’re only no fun Phil if you both have the clear ambition to get there in a certain timeframe, and refuse to listen to the implications. I actually think there’s a lot of nobility in your approach and wouldn’t mind learning some of those lessons– opportunities are simply not going anywhere (for most of us, we aren’t stock traders) we are artisan and entrepreneurs who can keep pivoting. So yeah, I’d prefer to choose a speed that resonates with both our sense of a great lifestyle and our sense of what the market will tolerate. this in many ways is what I”m focusing on right now in my life.

    I think I wrote the 1000 day post on day 1200-1500 ish.

  • YOUTUBE is holding me back. :)

  • You got it Ricardo, agree we need stresses and challenges to improve.


    Currently there’s a lot of guys I like to watch play, but Michael, you *had* to watch him.

  • I like the 2C’s here Josh… there’s a kind of courage that we are trusting in some positive outcomes in the face of a lot of uncertainty that can come from positive mind-frames (like experience) and negative ones (like being stubborn or ignorant). This might be why often those with “reasonable” mindsets– aka those in the middle– tend to miss opportunities that aren’t more or less handed to them.

  • Adrijus Guscia

    Oh haven’t seen Linsanity yet. Have to check out, thank you!

    If you liked Arnold’s Education of a Bodybuilder you might enjoy this one: Day in a Life type of docu.

  • Adrijus Guscia

    Devil’s invention damnit…

  • Very nice thanks Adrijus!

  • I found Arnold’s autobiography a surprisingly great read.

    He was an unbelievably motivated businessman long before the movies came along – I’d no idea.

  • Seth Overly

    Great post. I love the idea of setting 10k per month as a goal – even if you’re just starting out – make your first $1, then 1k/month, 3k/month, and on to 10k per month with unlimited potential after that. I think between 0-10k is where all the magic happens, where the ups are the highest and the downs are perhaps the lowest.

    It was 18 months to get to the point where I knew I wanted to start my own location-independent business to actually believing I could do it. Self-limiting beliefs, lack of grit (Give up Gavin) and lack of direction were the main culprits. It’s hard to say what exactly made it happen but the switch flipped and once it did I’ve gone from not only believing it’s possible, but actually believing it’s inevitable. About 2 weeks after the mental shift, I’m on the verge of going from 0 to my first $1 and couldn’t be more excited.

    You’re right on – there’s a lot of abundance in the world, you just have to see it, believe in yourself and keeping going, even [especially] through the hard times.

  • I heard the urge to give up is strongest right before a breakthrough. Maybe it’s Pressfield. Any truth to it?

  • not sure, might be structurally true, that is a breakthrough happens always after a period of no positive feedback, so the longer you go without feedback the harder it gets.

    i’m also not sure i recognized breakthroughs in the moment, or if what gave me momentary relief is what I’d identify in retrospect as important. hmm….

  • it’s funny you mention it, 0 to 1$ might actually be the hardest breakthrough.

    i also like the simplified goals of breaking it down by day and month and dollar

  • I still have the screenshot from that very first PayPal payment.

    It was meaningless as a sum of money (under 10 $)… but the ideas that somebody you’ve never met actually CARES – that’s mind blowing

    I remember somebody at the time telling me your first $ is like a new baby been born. I’ve never had a baby… but my business sure makes a lot of dirty diapers in its first few years !

  • big ed

    best line from the video…”string together days with efficient action and success can happen”

  • Adrijus Guscia

    Yeah, boring stuff but it’s the power behind success.

  • Danny Michlewicz

    This is a great article on Lebron, Jordan and Bird, 10-15 minute read.

    Few thoughts as I love this topic
    @Shayna – Thinking of a snapshot of your life 1 year ago is powerful – we change so quickly and dont know it. Theres an NLP audiobook I read mentioning that star athletes that overcome serious injuries share a few common characteristics, one of them being that they evaluate their daily progress based on the previous day. Today versus yesterday. They dont compare themselves to the best player in the league. That would just be depressing and useless. Similarly, depression and rumination is often linked to longterm thoughts of I will -always- by unhappy or something similar.

    One thought on abundance. Ive always found it hard to pass up money. Very hard. For the first time this year, Ive deliberately passed up on some short-term day to day grind opportunities. Knowing that when I get back to work the next day, or two days later, I will still be an expert and there will be abundant ways to make money gives me great peace of mind that lets me work on my weaknesses, enjoy life, and refocus.

    Another thought on money – sometimes we believe that making money should be a grind, so that when its handed to us, when we put in work and it starts coming easy, we dont feel like we deserve it. If we dont feel like we deserve it, we will get plowed over by the competition, and fall steps behind very quickly.

  • LOVE this article

    I’ve never had issues with your second point (passing on money) but your last paragraph really resonates.

    I’ve seen that pesky bugger a lot around these parts. Lots and lots and lots of entrepreneurs struggle with this– perhaps it’s one of the most stuborn remnants of the employee / industrial mindset. It’s tough to flush out.

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