How to Force Yourself to Ship (Even Though It’s Hard)

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It’s been a week and a half since we launched Drip’s biggest feature in 18 months, called Workflows.

Had we not committed to a deadline, in public, 2-weeks prior to the ship date (when we published this post and emailed a bazillion people), I believe we’d still be adding finishing touches.

It’s scary to ship. And it’s in our nature to want everything to be perfect before doing so.

When working in tandem, these two forces can keep you from shipping for far too long.

Enter Deadlines
This is why I’ve gone back and forth over the years about deadlines. Deadlines, especially those you commit to in public, are great at forcing you to ship.

But they can also have a negative impact on your quality of work (if you don’t give yourself enough time to do things right), or your quality of life (if you don’t give yourself enough time to do things right).

So personally, I don’t use deadlines all that much. But every once in a while (and especially when you’re just starting out), the discipline of a deadline works better than perhaps any other motivational tactic to force your hand and make you ship.

And with our Workflows launch, the deadline worked.

It forced us to make some tough decisions and get things out on time. And the launch turned out to be our biggest growth accelerator of the past 18 months. Hooray for shipping.

But committing to a public deadline is pretty scary. Here’s why you should do it anyway…

What You’ll Learn
If you’re doing things right you should be shipping a lot more than feels comfortable.

Especially in the early days, you should ship something monthly. Weekly. Maybe even multiple times per week (think of starting a blog and posting 2 or 3 times per week).

If you’re not doing this early in your journey, you’re not going to build up your shipping muscle. This is the muscle that’s weak and frail in all of us when we begin. And you strengthen over time through shipping, and shipping alone.

Shipping is also the event that gives you the rush.

This is the endorphin infusion you experience when hitting “deploy” on a new feature. Hitting publish on a blog post. Or launching an ebook on which you’ve slaved away for months.

The rush is the thing that keeps you going, yearning for the next time you can experience it. And if you wait too long, you forget how good it feels.

Don’t get me wrong, shipping is scary. It gets easier over time, but the fear never goes away completely.

I believe that our desire to not ship is created by multiple fears working in tandem with one another:

  • fearing people will criticize you
  • wondering if what you’ve shipped is good enough
  • wondering if anyone will notice
  • …and secretly hoping no one does

These are the big ones you’ll feel every. single. time. you. ship.

The answer? Strengthen your muscle. Ship more often.

It makes the terror decrease (just a bit). And it fires those endorphins that make you remember why it is you decided to embark on this journey instead of keeping your day job like a sane person.

How to Keep Shipping
Back to deadlines. A great way to force yourself to ship is to make an ongoing public commitment. Start a weekly podcast, for example. It’ll put your feet to the fire.

I’m pretty sure this is why Andrew Warner has shipped 5 interviews a week for years.

John Lee Dumas has done 7 per week.

Even schlubs like Mike and I have pushed out an episode every week for 3 or 4 years now.

I can’t speak for Andrew and JLD, but Mike and I are not particularly well organized. We don’t have our act together much more than the next person.

But after pushing a few episodes you start to feel like you’ve made a commitment to keep doing what you’ve been doing. It starts with a few weeks, then it’s a few months, then a few years.

By the time you get there you don’t want to break the streak. You’re a little scared to see what would happen if you missed a week.

Shipping is not only addictive, but it builds momentum and makes it easier to ship next week. And the next. And the one after that.

Public Deadlines
Maybe you don’t want to make an ongoing commitment, and just need motivation to get a big feature (or product) out the door. Your other option is to go old school and set a deadline. Nothing new here; we’ve all had them before.

But when was the last time you set a deadline for yourself and didn’t move it when things got tough?

I’m not talking about a deadline set by your boss, spouse, or local tax authority. I mean sitting down, choosing a realistic date. And, come hell or high-water, shipping by that date.

Even if your kid gets sick. Even if the next episode of Game of Thrones comes out. Even if you realize you missed a major piece of functionality and are going to have to scramble to fit it in.

Doing this will be both stressful…and exhilarating.

If you set a deadline and tell everyone you know about it, with one small motion you’ll start a silent timer. A doomsday clock of sorts. The pressure will build, but in the end you will push something out the door.

With Workflows we found a few extra tidbits we wanted to add before launch. We also realized we had overlooked re-working our onboarding flow to match the new stuff we were launching…but we didn’t push the date.

Because we’d committed to it in public.

But Beware…
There’s a balance here. Most of us are building companies because we want to enjoy the journey. So if you’re working yourself to death because you’re constantly setting overly ambitious deadlines, you’re doing it wrong.

If you go on one too many death marches due to unrealistic deadlines you’ll reach deadline fatigue, where they don’t motivate you any longer. Don’t do this.

I think it’s good practice to put your feet to the fire and commit to a hard deadline a few times per year.

For me, the two weeks after we set our Workflows deadline were the most productive I’ve had in months. Something about setting that deadline (let’s be honest, it was the fear of missing it) pushed me to become the highly-focused, insanely productive Rob I catch a glimpse of now and then.

So if you find you’re in a rut, not making progress, trying figure out what to polish next, or you haven’t shipped anything in months…set a deadline. In public. And see how it makes you feel.

Hopefully it scares the hell out of you. That’s how you know it’s working.

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