The 1000-Day Rule – Revisited 777 Days In


When I first read Dan Andrews’ post on the 1000 day rule of living the dream of entrepreneurship – before starting my business – I didn’t quite understand or identify with it.

In a nutshell, you have to be willing to be doing worse than you used to be at your day job for 1000 days – about 3 years – passing through various phases of uncertainty, trial and error, and wins and failures before you reach a reasonably comfortable and stable income level.

Now that I’m on day 777 of the process, I definitely understand and identify with Dan’s breakdown of the phases.

Why is it so hard?

1000 days doesn’t sound like a lot. High school is longer, so is college – and we all made it through those, right? So three years should be a snap.

Not so. There are HUGE differences.

In school, there’s a path to follow and everything’s pretty much planned out for you. Walk the path, manage to get passing grades, and you’re sure to come out the other end with a diploma. There’s also the instant-gratification feedback: you might spend five hours writing a paper, but next week the teacher hands it back to you with a grade. You know exactly where you stand and how you’re doing. Not only that, but there’s pressure from family, peers, and society to finish and not drop out.

In entrepreneurship, there’s no set path to follow (or, if you prefer, a million different possible paths) and no guarantee of success even if you do tick all the “right” boxes. You might put in five hours a day and not see the results for months or years… or ever. There’s no societal pressure to succeed; in fact, many friends and families do the opposite, criticizing and questioning the entrepreneur’s choices.

That’s why an entrepreneur needs not only an incredibly strong work ethic, but also a heck of a lot of determination or faith that it WILL work out (or: “I’ll find a way to make it work out, one way or another, and won’t stop until I succeed.”)

If you’re thinking of starting a business, ask yourself seriously if you’re capable of waking up every day and deciding to do five hours of work (no, Twittering and reading entrepreneurial blogs doesn’t count) with NO assurance it’ll ever be rewarded, and little to no feedback on whether you’re doing well, poorly, growing, stagnating, totally missing the mark, heading down a dead end, or building a real winner.

I can tell you from experience that it’s not easy; the mental and emotional discipline required is enormous. I have good days and not-so-good days (and even a stretch of bad months from which it was hard to recover).

But I can also tell you, having just begun to enter the “Sunrise” phase in Dan’s breakdown, that it is absolutely worth it. I’m loving my business and excited about its future – and I doubt I’ll ever go back to working for someone else.

Reflecting on how much I’ve learned and progressed over the past 777 days has really made me think: if I applied this kind of focused effort to other activities and areas in my life that I’d like to develop, what kind of amazing progress could be made in the next two years?

  • I love the analogy to college or high school and why it’s so different. I struggle with the same adjustment. It’s easy to keep going when the path is clear and you have all these self-reinforcing feedback loops. It’s harder (but a hell of a lot more fun) when you’re just plowing ahead into uncharted territory.

  • Dan

    Shayna this article makes me feel 1) so thankful that we are part of a community (that is facilitated and held together by blogs like this) that allow us to share ideas like this 2) makes me feel like I’m getting pretty old! and 3) like you are a badass. Keep rockin’ congrats on surviving to day 777!!!

  • Derek

    Hey Shayna,

    Nice write up and thanks for the update. I can really relate to needing a lot of determination and faith that things will work out and going through the ups and downs for long periods of time.

    I’ve been building up that emotional and mental discipline since moving out to Saigon in September. It’s been very difficult at times but every day you learn something and get a little bit better.

    Looking back at how far we’ve come is refreshing. It’s really cool how much we can accomplish with hard work and drive. Thanks for sharing!

  • 777..Lucky 7’s… But seriously Shayna, your post really breaks down what it’s like to be an road map and lots of uncertainty. Never really thought about the instant gratification/feedback from school, I like that analogy. Hopefully in about 3-400 days for me I’ll be in the sunrise phase of my business…;)

  • Keep rocking the path. Nothing beats being self directed, owning your failures, getting amped on your successes and skilling up until it all comes together into something you never imagined when you you began.

  • Ashley

    I’m brand new to the idea of entrepreneurship, so forgive me if this is a dumb question but is the business you’re talking about this blog or some thing else?

    • Shayna

      Hi Ashley! It’s not this blog – it’s

  • It’s a great post, Shayna. I am working hard on creating a mindset in which, however dire the circumstances are, I am in full throttle for as long as possible. Thank you for encouraging and showing me I’m not alone!

    • Glad you liked it! Definitely, if you can choose to give 100% regardless of the external circumstances (good sales day, bad sales day, etc.) you’ll be setting yourself up for success.

  • Barry

    Two posts in two minutes – I’m liking your work Shayna! I’d not encountered 1000 days befoe but I feel as if we’re living it somewhat – my wife and I can only cram in about 15-20hrs a week on our business after day jobs and three kids have extracted the bulk of out attention and energy…we’ve been at it for two years with no support, self-funded, pure faith and it’s just starting to pay off (though a month in Brazil for the world cup is taking us back a few steps).
    Look forward to reading more of your stuff

    • Wow, with all those commitments, I’m amazed that you’re able to invest any time at all… with 15-20 hours I’d say you’re doing great! It’s OK to be taken back a few steps if you’re doing something special to enjoy the fruits of your labor (I felt the same way with a month-long trip to Europe last year) – in fact, those types of experiences can whet your appetite for continuing to build a business that can offer even more freedom. Where in Brazil will you be?