The Value of Paying Your Dues

Paying your dues sucks. When I started my career, I got told by everyone older than me that whenever they handed me shit work I should be thankful because I was “paying my dues”.

I assumed it was some tired colloquialism for getting young people to do work at sub-market rates without questioning their own value.

No one ever really tells you *why* you’re paying your dues.

Telling someone early in their career that paying your dues has value is like telling a first grader that if they get amazing grades they can get into a good college and get a high paying job.

Until you’ve seen how gaining those experiences can meaningfully change the course of your life, you don’t really respect the value of that effort.

No one ever really tells you *why* you’re paying your dues.

With that, let me explain what I’ve learned from 23 years of starting 9 companies and watching thousands of other Founders pay their dues accordingly.  And before I go all “old man on the rocking chair telling kids these days to get off my lawn” let me start by saying I’m the most cynical person in the world.

So I’ll also point out where “paying your dues” is a crock of shit.

Paying Your Dues = Experience

Let me first explain what these “dues” actually are.

It’s not a hazing that you should have to endure just because someone else did.  That said, I actually think some people really do mean it when they say,  “I had a horrible time to get where I am so you should have a horrible time.”  However, any manager that tells you that is an idiot.  If someone can’t explain the value of the experience (which you may not appreciate) they don’t deserve your extra effort.

Your “dues” are the process of gaining first hand experience by actually doing something.

Your “dues” are the process of gaining first hand experience by actually doing something.  The problem is, especially early in your career, that this often involves having to do insanely hard work to properly earn that experience.

It often involves lots of sacrifice.  But in that hard work and sacrifice you start to forge real world experience that defines you.

Experience = Doing, not Knowing

The tricky thing about gaining experience is that you actually have to do something to gain it.  Just reading about a topic isn’t the same as having actually done it.

I watched this happen with my 4 year old daughter.  We would go on the back porch and she’d watch me burn grill food.  The first thing I told her is that the grill is crazy hot, and a great idea would be to never touch it.  She understood.

The information was in her head.  She knew the grill was hot and touching it was bad.

You already know what happened – because we’ve all done this.  At some point she touched the cover of the grill (which is also hot) and burned her finger.  Not badly at all, just that quick touch where you say, “Oh wow, that’s not awesome!”

She looked at me and said, “Daddy I know now why I shouldn’t touch the grill!  It’s hot!”  And guess what? She’s hasn’t touched the grill since.

My daughter just paid her dues.  She earned real experience that you can only get from doing, not just knowing.  No amount of explanation or information could supplement the first hand experience.

Tough Times are the Best Teacher

When I look back on my startup career and I think of all the valuable lessons that I’ve learned, do you know not a single one of them involves a positive, fun experience?  I can point to hundreds of lessons learned and hardly any of them are in sync with “well that was just so fun!”.

Here are some that come to mind:

• I learned why understanding your financials is so important when I racked up $100,000 in personal debt by the time I was 22.
• I learned why hiring your friends is a bad idea, when I had to part company with my closest friends.
• I learned why fundraising is so hard when I ran out of money and had to pitch 80 venture capital firms to get my teeth kicked in with the words “no” over and over and over.
• I learned why managing my time and stress was so important when my friends were taking me to the ER because my heart decided to give up on me.

In every single one of those cases I knew what the answers were.  I wasn’t suffering from lack of knowledge – I was suffering from lack of experience.  I hadn’t paid my dues yet.  I hadn’t forged my understanding in the cauldron of first hand experience.

Extraordinary Experience Often Requires extraordinary Effort

Obviously these experiences require time invested.  Theoretically there’s no reason that time can’t be allocated in a comfortable 9 to 5 schedule.

And yet somehow that never seems to pan out.

All of my experiences seemed to go hand in hand with extraordinary commitments of time beyond the bounds of a regular schedule. I’m not alone on this.  Every entrepreneur or extraordinary executive I know has had to put in ungodly amounts of hours, beyond what was allocated in a workday, to get truly exceptional experience.

Yet here’s where the requirement and message often get confused.  Your boss or mentor or some know-it-all-sounding writer like me, talks about how you have to invest extra time beyond your normal commitment to “pay your dues”.

Maybe what we’re really saying is that if you want accelerate your timelines of learning and experiences you simply have to invest more hours than your peers to get them earlier. Those extra hours cut into your personal time, your health, your finances, and your relationships.  That’s part of where you feel the “pain” that’s often associated with paying your dues.  It’s called sacrifice, and yeah, it sucks.

If you want accelerate your timelines of learning and experiences you simply have to invest more hours than your peers to get them earlier.

For those that are willing to endure that sacrifice to gain more experience to become a master of their own domain, the payoff is usually the ability to outpace the norm – your peers, your competition, your financial condition – and set yourself ahead.

Paying up without Paying out

The other crappy part about paying your dues is that it’s like writing a giant check for your favorite new toy and not knowing when or if you’ll ever get that actual toy.

Everyone tells you to write the check and the toy might come.  But you never really know if it’s true.  Which makes it really hard to write the check.

Your boss might ask you to work insane hours in hopes for a promotion.  Your mentor might tell you to continue to put your head down on your new startup in hopes that it will turn into something.  But you don’t really know if that outcome is guaranteed.

My rule of thumb is that if you can gain valuable experience, it’s worth it regardless of the payoff.  If you can gain valuable experience while also getting a great payout – bonus!

Experience is the Ultimate Weapon

The faster you can gain these experiences, the faster you can put them to work.  By the time I was 25, I was six years deep into learning with my first company.  I had made a colossal amount of mistakes which lead to incredibly valuable experiences.

That suite of experiences, gained through extraordinary sacrifice at a young age, gave me a unique perspective on how to operate in the next couple decades of my career.  These were experiences that almost no one my age had, thus my peer group lacked the ability to translate opportunities and threats into action the way I did.  That allowed me to start 8 more companies much faster than I could have possibly done without that earned experience set.

That doesn’t automatically mean that I would go on to do everything right. It simply meant that I was now armed with an amazing set of skills that would allow me to do more of what I wanted on my own schedule.  I learned firsthand how to avoid costly mistakes that would benefit me later in my career.

I found out that if you don’t put in the extra effort you forgo a ton of valuable experience. Without valuable experience you aren’t as capable as those who have it.

If you want to excel in this game, you gotta pay your dues.  And I can tell you after 23 years of sacrifice – it’s worth it’s weight in gold.