For a long time, I was playing business. Or rather, I was playing life.
I wasn’t taking it seriously. I was being an amateur.
I mean, I was serious – look at this face – but I wasn’t approaching my work or my life seriously.
I had struggled to get out of a crappy job, escape the midwest winters, and then got to California and life was relatively good.
Mission Accomplished.
I was always wary of becoming a “Thailand entrepreneur” – the digital nomads who traveled to Thailand to baseline their costs and figured out how to make $1k/month to live like a baller in Thailand.
This was the promise when I was getting out of my job – but the problem was with a lot of these guys – is that they never figured out how to make anything more than $1k/month.
They balled it up in Thailand because it was so cheap, but $1k/month is still $1k/month and that doesn’t get you much outside of SE Asia.
I never wanted to be that guy. And thankfully, between IMPOSSIBLE, Ultimate Guides, and X – I didn’t have to be. I was able to live between California and New York – bouncing around wherever I wanted, whenever I wanted. I went on a ton of adventures and even raised a bunch of money for charity.
But then I got a wakeup call.
I got sued. I started to realize how much stuff was working “okay”, but not optimal. I realized that I wasn’t taking my accountant seriously because “taxes were boring.” I realized that I almost lost my business because I didn’t think “lawyers were important.” I realized that my team building skills left a lot (and I mean a lot) to be desired.
The past few years have been a wakeup call for me. For me to turn pro. To focus seriously on what I’m trying to do at IMPOSSIBLE and in my businesses. In my life. In what I’m trying to do.
For a long time, I thought it was cool to be the “care free” entrepreneur. Live anywhere, do anything, anytime. No rules, no systems, no obligations, just the obligation to make enough money to have a good time doing whatever I wanted wherever I wanted.
- Don’t worry about team calls. If you miss them, you miss them.
- Don’t worry about showing up late, who’s going to fire you?
- Don’t worry about documenting or organizing stuff – that’s part of the fun of entrepreneurship, right? Winging it!
But over time, man – it wore on me.
- Wonder why your team isn’t engaged? Maybe because you’re not engaging them.
- Wonder why people don’t trust your plans? Maybe because you’re not showing up.
- Wonder why it feels like you’re doing the same thing over and over again? Maybe you should have documented it.
- Wonder why you’re stalling out on your fitness goals? Maybe it’s consistency.
The paradox of professionalism.
You gotta know the rules first before you break them. But if you break them, you better know them really, really freaking well.
The truth is, I avoided professionalism because it reeked of the shirt and tie culture that I tried really, really hard to escape when I was at my desk job in Milwaukee. I thought that sticking rules, hell boundaries of any sort (even a lease) was too constraining. And so I ran amuck in freedom – too much freedom (but that’s another story for another blog post).
The thing I missed was this:
Professionalism isn’t about looking a certain way, it’s about being a certain way.
You know what’s cooler than eating whatever you want, whenever you want, without judgement? Looking and performing to your potential and beyond.
You know what’s cooler than vaguely knowing your KPIs and thinking you’re doing “okay.” Actually knowing your KPIs and killing them, and knowing it for sure.
You know what’s cooler than feeling like you’re on a treadmill over and over, doing the same tasks again and again? Building rock-solid systems and teams to make sure they’re executed to the standard every, single time.
You know what’s cooler than hoping your trademarks are protected. Locking them down and becoming bulletproof.
You know what’s cooler than making mish-mash jokes about not knowing what your taxes are the past few years. Getting that ish on lock and getting out in front and doing projections and planning for future years.
You know what’s cooler than being the “carefree entrepreneur”? Being a pro.
Pros don’t show up only when they want to.
They don’t show up only when they feel like it.
They don’t show up only when it’s convenient.
They show up because it’s their job.
And they do it well. Every time.
Finances. Trademarks. Organization. Documentation. Processes. Teams. Systems.
They all sound contrarian. They lock you in. They force you to show up. Do things a certain way.
And they’re all constraining things.
But when you’re forced to show up, the paradox kicks in.
The more you show up. The tighter you’re locked in. The more ability you have to improvise when you want. The more professional you are, the more freedom you gain. As Jocko would say – #disciplineequalsfreedom.
So that’s the job.
That’s the gig.
You picked it.
Now be a pro at it.
Show up.
And do the damn thing.
If it’s worth doing, it’s worth doing seriously. You’re not helping anyone by slacking on that front.
Being an amateur isn’t cool. It’s not cute. It’s not funny.
It’s just amateurish.
And the worst part is, being an amateur in one thing, will start to seep into everything else.
How you do anything is how you do everything.
So if you’re going to do something – be a pro at it.
Steven Pressfield has a book on this subject (Turning Pro). I’ve read it years ago, but it’s always good for a kick in the butt. Be a pro. Be better.
I really like the tone of this post. It’s very on point: “And the worst part is, being an amateur in one thing, will start to seep into everything else.” resonates with me.
Also I’ve been in situation with too much freedom on my hands that I didn’t know what to do with it and found a bunch of minor problems to deal with just to keep myself busy. I’m looking forward for you post on that.
P.S.: I like how you transitioned from email to blogpost.
I love this post!
You can say this now, now that you’re raking in the Big Bucks, now that you have a lot of products generating revenue, now that you have a “team” working for you or with you or whatever the current jargon is for having employees or contract workers. You can say this now, after spending years jetting around the world to different countries on a whim.
But here’s the thing: you didn’t KNOW this stuff when you started. You didn’t KNOW this stuff when you ran your first indoor tri, or when you decided to get six-pack abs and do a photo shoot, or when you released your first app.
And if you had taken the time to learn all this stuff first, you wouldn’t have done any of it. None. Zero. You’d still be sitting in the basement reading books and studying copyright law.
Look at the list you just laid out here. Look at it, not from your current “six figure” (probably seven figures, now, huh?) or more revenue stream, but from the vantage point of the guy living in the basement. If you had seen a list like this back then, I don’t think you would have even started. You didn’t have any money, for one thing. How are you going to start registering trademarks and hiring lawyers and accountants when you have no money?
Sure, there’s a time to “go Pro.” It sounds like you’re there. It sounds like you’ve gained the experience and knowledge to know what “going pro” means.
Plus, you can afford it. You can afford attorneys and lawyers and a staff. That is, you can afford it NOW.
You couldn’t afford it then.
You had the discipline. That’s been your thing from the beginning, and you’ve refined your focus over time. But you didn’t have the resources then that you have now.
Don’t get me wrong. I am beyond astonished at what you have created with Impossible. I’ve been watching and following since The Blog of Impossible Things. I am impressed and amazed and, of course, a little bit envious.
But that dude who was buying second-hand bikes off Craigslist to compete in triathlons was in no position to be hiring lawyers or researching copyright law or “partnering” with other businesses. He was exchanging tweets about how much water he was drinking per day with the guy who ran another fitness blog, and gradually trying to figure out how to “monetize” the growing popularity of his own web presence.
If that second-hand bike riding triathlete had looked at the list you’ve posted here, it probably would have seemed overwhelming.
So tell us, Joel: how many countries did you visit BEFORE you filed for your first trademark? If you were spending all your income on attorneys and accountants and trademarks, would you have been able to do as much traveling? Would you have been able to complete the 777? Would you have had the money to contribute to Pencils of Promise?
And from your basement apartment, how long would it have taken you to research, study, and learn… on an academic rather than a practical basis… all the stuff you’re now telling would-be entrepreneurs they need… NEED… to know and do?
You know it now, you’re doing better than ever (and, I’m sure, better than you ever thought possible), and you’re learning and adapting and evolving (I’ve noticed that “evolving” is a trendy term right now). This is where you’re at now, this is what you know that you need to do now, and maybe should have done earlier. But you didn’t know this stuff earlier, and some of it you couldn’t have done because you weren’t pulling in the Big Bucks. And some of it would likely have prevented you from doing the things you did then to get to where you are now.
It’s good advice. It’s good advice for entrepreneurs who have achieved a certain level. It’s good advice to keep in mind for a business looking to grow.
But I don’t think it’s necessarily ESSENTIAL to apply everything here from Day One. In fact, contrary to the over-arching theme of IMPOSSIBLE HQ, I don’t think it’s even POSSIBLE to hit the ground running with a posse of attorneys and accountants and staffers already on board. Unless you’re already loaded. Unless you already have a business plan. (Like the dude in the basement had a concrete, defined, the-bank-will-loan-on-it caliber business plan? Yeah, right!)
Interesting post, for sure. Thought-provoking, yes. Excellent advice and information, certainly. Potentially discouraging for beginning entrepreneurs looking to break out of a rut or strike out independently? Yeah, probably that, too.
Hey man,
Definitely – it’s a growth thing. Things change as you grow the business. I like your points, and they’re worth thinking about, but the key point here was that I could look in the mirror and know I wasn’t meeting the standard I had set for myself. That discipline you mentioned? To be honest, I let myself slack. That’s what I’m talking about. It’s not about spending money, or hiring lawyers – but it is about how you approach those things.
You can do taxes yourself without hiring someone. You can file a trademark without a lawyer. If I would have done that back in 2010 when things started, then I wouldn’t have had to take the 18 month break in the middle of 777 to handle the lawsuit. The $300 it takes to file a trademark pales in comparison to what the lawsuit took to handle.
Maybe I’m at a different point than some entrepreneurs – that’s fine – maybe the specifics of the post isn’t for them – BUT – that said – the attitude and the approach you take – whether you’re filing your taxes yourself or have your own dedicated firm is what matters.
My approach wasn’t up to my standards. So, I’ve been working on fixing that.
p.s. Always appreciate your historical posts – keeps me grounded 🙂
Thank you …just downloaded TURNING PRO …I get it – but I still need the kick in the pants – to live HOW YOU DO ONE THING IS HOW YOU DO EVERYTHING.
Thanks! i just finished Pressfields book…and bought two as christmas gifts…it was like your work…short, to the point, pithy.