How to Accidentally F*ck Up Your Career Every Day!



The world is filled with blog posts and clickbait that will tell you the seven hacks you need to do to become super successful, wealthy, and powerful and to climb the corporate ladder.  These drive me nuts for multiple reasons! It seems so easy – like any other “hack” – and for the most part provides very little in terms of actionable, specific ideas that you can actually put into place.

So I decided to write the exact opposite post – a simple formula about how you can accidentally screw up your career each and every day. Ready to learn a specific plan that you can follow immediately? Read on!

First, a bit of a confession. My career to date has been pretty good by most standards but in reflection, most of my success came from luck, hard work or being in the right place at the right time. Usually a combination of all three. Not exactly a repeatable recipe for success. As I get older I have become more than a bit obsessed with how I nearly screwed up multiple times – but for a few lucky breaks it could all have gone much, much differently.  

Second, my observations are not scientific in nature but rather a result of a long debate among the investment team at the venture capital firm I co-founded, Next Coast Ventures. Our team recently had a long working session where we reflected on what makes a truly great leader, entrepreneur or executive. We looked across the 50 companies we have invested in – as well as our own career – and debated how equally qualified executives can end up with wildly different career and business outcomes. Why do some entrepreneurs seem to turn an idea into something massive while others – with an equally great idea and resources – screw it up?  

The bad news? We could not find one single, magical attribute that makes a difference. In professional basketball, height really does make a huge difference. In business, there is no equivalent to height. However, we were able to come up with a consistent list of attributes that seemed to repeatedly lead to career failure. Call this an “anti-hack” blog post. Here are the five ways to accidentally screw up your career each and every day. Please don’t try these at work!! 

  • Lose all of your self-awareness. This seems to be the quickest way to throw your career off track.  Ask any great athlete what they work on in the off season and the answer will be very simple – their weakness.  If LeBron James missed a lot of free throws in a season, you can bet he works on that part of his game all season ( But ask most professionals what their weakness is, and they will likely get defensive or stumble for the answer.  Self-awareness is the starting point to understanding what you are good and what skills you lack. Losing any and all self-awareness is the quickest way to stall out your career – you have no idea how to improve yourself and your skill set.
  • Refuse to get coaching or mentorship.  The best athletes have multiple coaches.  Why wouldn’t you invest in your own career as well? It doesn’t have to be paid coaching – it can be a mentor or friend at a similar stage in her career. An external source of input enables you to gain perspective and acts as a sounding board on a wide range of professional development topics. Not having someone help you manage, consider and develop your career is a sure way to have a short but average career!
  • Try to be someone you are not.  I am not referring to the instant classic Zoom conference call fails here (which are funny and cringe worthy watching for sure). I am referring to the person who tries too hard to be something he is not. I am talking about putting on an act and lacking authenticity. Be it the sucking up, boasting or simply being afraid to say “I don’t know” – the person who is play acting never really makes it to the next level. Failing to be yourself is one of the easiest and quickest ways to screw up your career!
  • Don’t work hard.  One of my first bosses gave me magical advice early on in my career –get to work 20 minutes before your peers and stay 20 minutes later each and every day – and use that time to do a bit more than anyone else. That is only 40 minutes a day – a little bit longer than one show on Netflix! Use the time wisely (not for facetime or to show off – do real work) That 40 minutes a day equals 3.3 hours a week and that turns into 165 hours a year! Assuming you won’t have to work hard to get ahead is a short sighted way to get nowhere in your career. Said differently, it is quite easy to live a hard life…
  • Expect the world to help you.  Young professionals entering the workforce for the first time really struggle with this one. Like rain on a 4th of July parade – it can be really hard to understand that the world really doesn’t care about you, your career or how you advance and learn. It is hard to be prepared to run head first into a wall of indifference, especially when you are trying to get ahead, but that is the reality of the professional world. Waiting for someone (other than your Mom) to really care about your career will really only bring one – a really, really long wait.

So there you have it – the five easiest ways to completely and accidentally fuck up your career each and every day! Pretty easy to follow along, huh? The good news here? The opposite of each of these career fails brings just as much potential and upside to advance your career – and all are pretty easy to obtain. 

There are some great blogs on how to get better at self-awareness, and this in turn can provide input on how to get a coach or mentor. An authentic google search will yield some great books – my favorite is Start with Why – but there are a ton of great reads on the topic. 

Hard work – well unfortunately that is as simple as it gets. Last but not least, the world may not open its doors to you but that too can turn into motivation – just keep telling yourself “if it is going to be, it is up to me”. Watch how contagious that attitude is and over time the right doors will open – even if you have to kick them in once in a while!

You may think you want to be an entrepreneur but maybe you need to take a real look at where you are at first. Take the Entrepreneur Survival Test. 

Monkey Masters: Jason Dorsey

Monkey Masters: Jason Dorsey

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