This one goes out to all my someday-maybe peeps. You know who you are. You, the one with the dreams, lying sleepless in bed in the dark, wondering:

Is it even possible for me to change? After so many years?

The answer is yes. Hell yes.

And it’s easier than you think.

The next question is, of course, how?

How do you go from being an inveterate procrastinator — with a lifetime of bad habits, notebooks full of unexecuted plans, hard drives full of dead dreams — to owning a million-dollar-a-year business?

That’s what I’m going to illustrate for you today, drawing from two decades of embarrassing stories about, well, me, your friendly former inveterate procrastinator.

I know you probably aren’t prepared believe me yet — you’ve had so many years of failed starts and false hopes. There’s a lot of bullshit peddling out there, too. That’s okay. I’m not offended. You’re right to be skeptical. But I’m going to open up to demonstrate my bonafides to you.

And I’m going to share with you every thing I did that made a difference.


It took me 11 years to go from my first plan to our first seven-figure year.

In the startup world, that’s considered a long-ass time.

Certainly it’s not the kind of speed that would get me into 30-Under-30 (plus, that ship has sailed; but you won’t find me today in the 40-under-40, either).

Here’s an annoying fact: We could have gotten here much, much faster. Without a doubt. I lost a lot of momentum to chronic illness, but the greatest delay of all was the time I spent dreaming and planning and procrastinating.

We could have been here at least five years sooner if I hadn’t fundamentally misunderstood the way to start.

If you take away nothing else from this litany of things I wish I’d done differently and sooner, it’s this:

You can achieve more and faster than me, if you’re ready and willing to do the right things at the right time.

Without further ado, let’s trip through my past and see all the times I fucked up and all the opportunities I could have seized sooner, faster, better. Eveyrbody loves an embarrassing story!

Let’s start at the very beginning…

The year was 1997.

I was 13, extremely online, a devoted reader of WIRED magazine… and I knew exactly what I wanted to do with my life: write books, design software, build businesses, and sell them. This was the exact moment when the term “serial entrepreneur” was rocketing up from nowhere to become a popular term of art. The minute I heard it, I knew I wanted to be it.

Even at this age, I had a pretty good handle on my self: I was big into starting things, finishing them… not so much.

The spectre of having to finish made me feel sick inside.

Flip forward to 1999

High school. I’d write my papers while eating breakfast in the morning the day they were due; on the bus with squiggly handwriting thanks to the crappy suspension; in one special case, I wrote out my English homework while the teacher was circulating the classroom, checking everyone’s English homework. I got great grades and I was bored out of my mind, aside from all the hours I spent raking myself over the coals for not preparing, and the times I raced up against the deadlines.

I work best under pressure, I thought. That was the only explanation I could come up with to explain why I couldn’t just sit down and do the work like the other kids.

This isn’t a work illustration, of course… but it sets the tone for the next near-decade.

In 2004, I started to plan

I was 19, a freelance designer/developer, and full of it — knowledge, ideas, bravado — lounging in bed under the rumpled covers with my iBook G4 propped up on my knees, excitedly vomiting ideas into my xPad notebook. I was going to build a better Basecamp. Basecamp was designed by people used to making web sites, not software. By this point, I’d been obsessed with interaction design for a decade. I knew I could do better. And, with my web app development experience, I knew how.

Not that I did a single thing about it, of course.

Instead, I kept on doing what I had been doing for years: freelancing for clients I didn’t like, my hair much too much on fire to take a step back and set a career direction; feeling that terrible sinking sick feeling when I got overwhelmed, waiting for the deadlines to force me to do my damn job. Falling behind and telling little white lies to get out of it. Even when I did hit the deadlines, it was such a stressful way to live.

A year later, in 2005

I was older and wiser, 21 and significantly less full of it. I had just been taken for a ride by a con artist client who nearly left me homeless, with a workload that had knocked me completely on my ass. Out of financial necessity, I hung up my freelance spurs and took my first-ever full-time job working for a tiny development agency with big, important customers in Washington, DC. On Mondays, I took the metro to G Street and sat in my uncomfortable clothes in the tiny, windowless office. You know the kind: grey carpet, grey lighting, grey cubicles. The grey was maddening and so was the work; it was the first time I ever rubbed shoulders with senators, and also the first time I attempted recurring datetime development.

I was often behind. But having a regular job seemed to help.

Still, I harbored my dream of building a better Basecamp… even more so, frankly, as it became clear that the SaaS model could really work as a business. (What can I say: I love money.) I pitched my ideas to my boss, hoping for a partnership; he nodded along enthusiastically to all my carefully laid plans and forecasts. And yet, he never seemed to want to actually start it.

Client work just kept cropping up.

I, myself, did nothing.

2006

I had a new job and a new set of skills: Rails (then sub-1.0) and modern, interactive JavaScript. There was definitely no chance of pitching my new employer (who hired me as a skilled grunt for professional services), so I didn’t bother trying.

But I did blog about what I was learning, and as a result I caught the eye of O’Reilly editors who offered me a pretty phat book contract. At the time, there was very little on modern JavaScript, and nothing on the rising frameworks (Prototype, Scriptaculous, Moo, and so on).

I proudly signed the contract, negotiated a 4-day work week to focus on writing, and recruited some nerds I knew to help me write the individual chapters, each focused on a different tool. All but one of my coauthors let me down. For once I kept working — I was working my ass off, all by myself on the 500-page behemoth which was quite late, in no small part due to other people. But one day, O’Reilly told me, “You can’t slip any more, and you can’t quit.” The contract said no such thing. Well, the one thing you never want to try is to trick me; I quit.

300-some pages of content sat, unused and unloved, on my hard drive.

And then it was 2007

Another year, another job; this one, the strangest of all. I was working at Limewire, of all places, on a skunkworks project — a web-based social network for artists. Never heard of it? Yeah, there’s a reason. One of the older employees managed to trick our child-like employer into funding his PhD project, a Ruby-based implementation of WebDAV. We were to build our web app using this as-yet-nonexistent server as our backend. It was a mess.

Near the end, our capricious boss brought in a new, adult CEO and I found myself sitting on my front stoop, leaning on the metal rail and arguing with him on the cell phone. Naturally, he wanted to kill our nearly-year-long project because we had not been able (been allowed) to ship it. I told him, “We’re 9 months pregnant and you’re talking about abortion.” (Not my finest metaphor.)

We never launched anything, not even so much as a Coming Soon page.

I stayed just a few more months.

And now we come to my favorite year, 2008

This year is full of pivotal stories because this was the year that I changed everything.

I had quit my job at Limewire and was back to consulting, high end design work this time, and far more business-like than I’d ever been before. I still had troubles with deadlines and thriving-under-pressure and all the same delay-stress-freakout-race kinda crap.

But this story isn’t about the consulting projects.

There’s a single thread that defines this year for me and it starts like this:

It was December, and chilly, and I was in a hot shower with the window cracked open for a cool breeze and a view into the beautiful oak tree that grew just outside. My head was spinning with elaborate plans for a visualization art installation, powered by tweets. (I just knew the internet would go crazy for it.)

In February, we pitched my idea to Twitter and Ev himself at a huge conference table in their Southpark office. A few weeks after that, they told us they “couldn’t get it together” to hire us to get it done.

In May, I was in Vienna, Austria, lying in bed once more, laptop on my knees, while my future husband Thomas was relaxing in the bath. My mind flashed on back on all my elaborate plans over the years, and all my attempts to get someone to pay me or even just work with me to build the things I wanted — and how it never fucking happened.

Why was I waiting?

I decided to stop. waiting. and just fucking SHIP it.

Right then and there, I whipped up a tight, extremely limited design and accosted Thomas in the tub to ask him about fetching JSON in the front-end to drive a much, much simpler visualization. Screw backends. Screw all the pretty graphs and filters. Screw any kind of interactivity at all. Screw dreaming. Screw waiting.

When he got out and dried off, we built it. And shipped it. That very same day.

People loved it… but far more importantly, I loved it. It felt amazing.

That was Twistori, and the rest is history.

That was the first time, ever, that I let go of all the sturm und drag of elaborate plans, fantasies, deadlines, pressure.

It was my first taste of being fully in control of what I was doing, the only one with my finger on the launch button…

…and I knew I could never, ever go back to the way things were before, with bosses, clients, the pressure, and my own self-sabotaging plans.

What followed was the most incredible 12 months

We launched our first SaaS in December 2008. It took 3 months of Fridays and sometimes Saturdays. It had an absurdly limited feature set. My only goal was to just fucking SHIP it.

We launched our first technical ebook, in January 2009. It was only part done, a beta. My overriding goal was to just fucking SHIP it.

A programming workshop followed. Turns out workshops are amazing to just fucking SHIP, because a huge part of the “product” is actually the live performance, and people are far less critical of a hiccups when you’re standing there (or on video) live in front of them.

I harvested the corpses of my long-dead dreams, and turned them into fertilizer.

And this is something I’d like to point out: I took the ideas I had been deliciously planning for so so long, but rather than attempt to boil the ocean, I broke them down into parts I could cobble together to (you guessed it) just fucking ship.

Freckle (not a project management app) rose from the ashes of my five-year-old dream for “better Basecamp”; from the old, neglected docs of my O’Reilly book came our book on JavaScript performance, and later our JavaScript Masterclass.

In December 2009

I mulched the story of my sudden change — and my experience launching an ebook, a workshop, and a SaaS — into the very first (tiny!) Year of Hustle. My v1 was nothing more than a 2-hour teleconference call (remember when those were a thing?) plus Q&A. It took just a few hours to produce and just fucking ship. Eventually, that evolved into 30x500.

Five years later, in 2014

I wrote the first draft of a little book called Just Fucking Ship in a mere 24 hours. I blogged its creation live, in public.

And then as the clock striked 00:00, I shipped it, rough as it was. To — say it with me — just fucking SHIP it.

Because by then, I knew the score:

The tiniest thing shipped is better than the best thing planned.

Don’t get me wrong: A good plan is worth its weight in (future) gold.

But when you suffer from procrastination, if the driving force of your plan isn’t to ship something useful as quickly as possible, then the plan isn’t good. The plan is bad.

All those years of elaborate, delicious plans had done nothing for me. They just got more and more detailed and amazing, and every refinement took me further and further away from actually shipping anything.

Ever.

So, enough about me. Let’s talk about you.

What can you do today to overcome procrastination and just fucking ship?

A bad plan — most plans — will actively keep you down.

You’ll keep working on the plan, expanding it and changing it, trying to short circuit the flaws you imagine and foresee, to eliminate the chance of failure, to route around the problems in your mind…

You can fiddle with that plan forever.

And if you’re anything like I used to be, you will.

That’s the bitter paradox: the more you struggle to guarantee your future success with a ‘bulletproof’ plan, the more elaborate it becomes, the more likely you are to accidentally destroy your future by never taking action to bring it into reality.

You build a future with actions, not thoughts.

Not feelings. Not pressure. Actions.

That’s why the best plan is to learn how to plan just enough and with the right elements to help you just fucking ship.

In 2008, I had been about to repeat that planning mistake with Twistori. But when I cried, “fuck it! ship it!” — I pulled myself back, for the first time ever, from the vicious cycle of elaborate planning.

The Twistori I had imagined bears no resemblance to the Twistori we shipped.

But the Twistori we shipped brought us reknown, opportunity, and money — and a transformative experience for yours truly.

Procrastinator, you can heal yourself with this mantra:

  1. The more you do,
  2. the more you ship,
  3. the more people you reach,
  4. the more you learn…
  5. the more you can do next time

Sure, I learned some things by analyzing Basecamp in 2004, and writing down all my private thoughts in my little private notebook.

But I learned a million times more when we launched Freckle, as rough as it was.

And I made millions more dollars, too. The lifetime revenue for Freckle alone is just about to cross $4,000,000… which is 4,000,000x what my imaginary Basecamp Killer made 😂

More importantly…

At 34 years old, I’ve fulfilled my dream from 21 years ago, with just one tiny tweak: I write books, design software, build businesses… and keep them.

It turns out that just fucking shipping things is magic… but the real fun is in growing and shaping them and reaping the rewards.

But you’ll never get there if you don’t ship.

Scope, chunk, motivate, execute, and finally launch your project!

Join our challenge to get 6 weeks of rules and tricks from our personal playbook, along with personal stories and case studies to help you get that thing you've been wanting to finish, shipped.

When you subscribe, you’ll also get biz advice, design rants, and stories from the trenches once a week (or so). We respect your email privacy.