GarrettDimon.com

Since day one, I’ve always felt like I was behind. I was moving too slow. I could never catch up. Our customers wanted, even needed, improvements. I rushed and hurried and worried. I bounced around from this enhancement to that. I got away from exploring ideas and just built the first solution that came to mind. It got the job done, but deep down, I was usually disappointed with the results.

I thought that was how it worked. Everything needed to be done yesterday. I didn’t necessarily work absurd hours, but I didn’t slow down and really take my time to find a great solution. I just raced to get it out the door so I could get to the next thing on the list. I couldn’t keep up with the ideas and requests that thousands of users inevitably generate. Even today, I still struggle with this. I want to make it easier for them to work, so I worry and hurry.

As it turns out, learning to let go and take my time has been a powerful lesson. Improvements are no longer a race where I start out two laps behind. They’re a journey where I’m exploring to find the best solution; not the quickest. I’m measuring success in days or weeks instead of hours. Writing code is fun again. That fun is inevitably translating into a better Sifter for our customers. That was the whole point in the first place, right?

A few weeks ago, we released a significant update to Sifter. (Rails 3, Ruby 1.9, and a bevy of associated gems and other components in case you’re curious about such things.) Since then, there have only been a few fleeting moments of peace and quiet. My Pavlovian response to the email alerts has gotten a bit out of hand.

The first couple of weeks after the release I felt physically ill due to the extended hours and the pressure I was placing on myself. You see, it’s simply not possible for anyone to be harder on me than I am. That’s both good and bad. Maybe more bad than good. Anyhow, it was a little bumpy. From obscure encoding bugs to even more obscure performance bugs, (you know, the kind that only show up in production) it’s been a wild ride.

More often than not, going to bed only crossed my mind when I recognized that being at the keyboard would likely do more harm than good. Of course, most nights, going to bed didn’t equate to getting sleep. There were just enough emails to prevent any deep restful sleep. There were rarely any that required immediate attention, but I wasn’t taking chances.

I’ve never worked so hard or been more physically exhausted by work in my life, but do you know what the crazy part is? Despite that exhaustion, I’ve never been more excited or anxious to get to work. The boring part is done. Now it’s just about delighting our customers with long overdue improvements. I know I need to catch up on sleep, but now I don’t care. I don’t want a break. I just want to ship things and make people happy. Nonetheless, I’m going to take a break tomorrow. Or maybe the next day. We’ll see.

We spent the last 6 months doing hard work that isn’t fun or directly visible to customers. It just had to be done. It sucked. Building this foundation has been the hardest, most involved work with which I’ve ever been involved, and nothing has ever pushed me so far outside of my comfort zone. Conveniently enough, my daughter is 6 months old as well. Put the two together, and well, you can probably guess what kind of a ride it has been. Thankfully, it looks like the most challenging days are behind us, and we’re ready get back to making a product rather than managing a business.

Team We have awesome people on retainer to help with necessary but distracting things like bookkeeping, accounting, legal, system administration, and more. We also have enough profit to bring in some additional help from time to time so we can work with great people on fun stuff.

Technology We have the technical infrastructure in place to serve more requests than ever with our fastest response times ever, and we’ve just barely dipped our toes into performance tuning. We can also quickly and easily scale that infrastructure as we grow. Our other internal processes are running more smoothly than ever. We’ve refactored and improved significant amounts of code so that we’re running the latest and greatest with the most flexibility to adapt going forward.

Knowledge We have three years of interacting with real people using Sifter and offering great feedback and insight to how they use it. Those conversations have helped us create a crystal clear vision for where to take Sifter from here. We’ve also been able to observe how people really use Sifter. We have a clear understanding of which features see the most use and which features we could probably live without. I can’t put into words how excited I am to do something with all of this accumulated knowledge.

With Sifter, all I ever wanted was to build something that made people happy and have fun doing it. In some ways we’ve succeeded, but it’s been significantly more challenging than I ever anticipated. In four years, all we’ve really managed to do is build a business that can afford to let me turn Sifter into the product I always envisioned. This is just my way of drawing a line in the sand to say this is the week that we turned the corner. Check back in with me at the end of the year to see if we pulled it off.

When I set out to build Sifter, I had a singular vision. Make a bug and issue tracker that non-technical team members would actively use. However, once it was out in the wild, things weren’t so clear. I failed to stay focused. I let myself get distracted by finances, logistics, uptime and support.

I got bogged down watching our bottom-line even though we’ve always been comfortably profitable. I worried about preventing fraud even though the only instance we ever encountered only cost us $200. I constantly worried that Sifter could go down at any moment even though we’ve had 99.96% uptime since launch. (That’s about 9 hours in almost 3 years.) Don’t get me wrong, we’re working to do better, but at 99.96% there’s more important work for us to do. I also let myself become too focused on support. I desperately wanted people to like Sifter. If they didn’t like it, I wanted them to understand, and ideally, appreciate the vision. All of these little things were distracting me from the work that really mattered.

Once Sifter was live, I went from creating an application to running a business, and it didn’t take long before that business was running me. Between fear, worrying, and the feeling that I had to justify our every move to our customers, I stopped having the guts to try and do anything special with Sifter. I was so obsessed with ensuring that we didn’t fail, I forgot to spend time making sure that we succeed.

It took the biggest deadline of my life for me to see what I’ve been doing wrong. In about 4 weeks, if all goes well, my wife and I will have our first child. I’m not even close to finishing the amount of work that I had hoped to by then, and until recently, it was killing me. However, it has helped provide a renewed focus, and the next 4 weeks will see some of the deepest improvements to Sifter since we launched because they set us up to minimize the distractions of running Sifter.

By the time our daughter arrives and I hopefully get a little bit of time off to spend with family, Sifter will be in a new hosting environment with improved performance, higher availability, more modularity, and even better backups. That means fewer logistical distractions and more time to focus on improving the application itself. We’ll be able to grow faster and with less effort. On top of that, we’ll add one of our top three feature requests with the other two to follow not long after.

I’ve always known better, but I simply couldn’t see it. Building a business is scary. Starting a family while building a business is even scarier. However, letting fear and worry drive decision making is no way to accomplish anything meaningful. I just wish I had recognized it sooner.

I’ve designed and created software and web sites for a lot of different companies over the years. All of those companies have been focused on features or just getting something out the door. They were more concerned about next week’s trade show than next year’s vision. They would rather have one paying customer today than one passionate customer tomorrow. I always understood their reasoning, but I never shared it.

After investing 100’s of hours in designing the future vision for Sifter, I’ve finally had the opportunity to put my money where my mouth is. Instead of chasing the all-powerful feature checklist, we’ve made a pretty big bet that improving the overall experience of using Sifter is a better decision than adding as many features as we can. That’s not to say that it’s right for every piece of software—only that we feel it’s right for us.

Spending such an incredible amount of time on design isn’t easy when the occasional customer cancels and tells you that they’re doing so because of your lack of features. However, staying true to this vision feels like the most important decision that I make every day. It’s frustrating at times because this is a massive exercise in delayed gratification. I just have to remember that we’re thinking about 5 years from now not 5 months from now.

Naturally, we’ve got a long journey ahead of us, and there won’t be a single moment where we unleash a 2.0. Instead, we’re going to finish laying out the vision and then steadily evolve towards it. To some degree we’ve already started the evolution. We’ll still be adding features as we go, but we’ll always put design and user experience first. We’re not going to add a feature simply to have it on our checklist. When we add something, there’s going to be a good reason for it, and we’ll be designing it carefully. That is, we spend about 3-5 times as much time thinking and designing than we do building. We don’t want to placate customers today—we want to give them a reason to love Sifter tomorrow.

Sometime around 2002, I attempted to start my own business, not as part of the grand plan, but rather as a fallback for lack of options. It didn’t do so hot. I was living at home and the highlight of each week was meeting up with friends at a bar on spinner night where you would spin to find out the price of your beers. (Anywhere from free to $1.) I digress.

That business lasted a couple of years, and if I had to guess, my effective hourly rate was about $1-2 an hour. I was under the impression that 60-80 hour weeks were the way to do it. I thought that If the company wasn’t succeeding, it was simply because I wasn’t working hard enough. Inevitably, I would get burnt out and be wildly unproductive for weeks at a time.

Eventually I realized that I needed to move on. Despite being a complete failure in and of itself, that experience contributed enormously to my ability to launch Sifter. More importantly, as I look back on that time these days, the importance of having a healthy work/life balance was the most important lesson of them all. That’s not to say that it’s important for everyone, but it’s very important for me.

Fast forward 6 years. I launched a hosted web application that’s available 24 hours a day and 7 days a week. I’m essentially always on call. I got a dog, got engaged and subsequently married, bought a house, and did a handful of other things that made absolutely zero sense from the standpoint of managing a young business.

There’s no doubt that those decisions made Sifter more difficult. Much more difficult. Raising a puppy. (You don’t realize how often they go to the bathroom until you’re trying to concentrate on writing code and you have to stop regularly and carry them down three flights of stairs.) Planning a wedding. Going on a honeymoon. Buying a house and committing to a mortgage.

We all have our priorities, and different things are important to different people. Nothing wrong with that. This time around, when I set out to build a business, I promised myself not to let it get in the way of living my life. It hasn’t been easy, but for me, it’s clearly been the right decision. From where I’m standing, Sifter wouldn’t be what it is if I wasn’t actively making sure to have a little bit of a life on the side.

Finding time for all of these things required a lot of time and effort. It’s been worth it, though. Had I put those things off to focus on the business, I can assure you that the depth of my regret would not be quantifiable. So, next time you read an article with the media glorifying somebody starting a company and working 168 hours per week, don’t assume that’s the only way or even the best way. It’s just one way. It’s just as possible to have your startup and friends and family too.