Chapter 8: Ongoing Education

You don’t learn to walk by following rules. You learn by doing and falling over.

Richard Branson

Even if you believe that you’re a generalist with a wide range of knowledge, starting a company will quickly expose just how much of a specialist you are. Even with a couple of cofounders, the breadth of knowledge needed to launch a hosted web application is enormous. If you’re a sole founder, it’s effectively impossible to know everything from day one: design, front-end, back-end, database, server, security, marketing, business, pricing, support, release management, and more.

Let’s break down front-end development: HTML5, CSS3, transitions (animation), SASS, Compass, LESS, CoffeeScript, jQuery, Ajax, web fonts, HiDPI (Retina) displays, responsive design, and a proliferation of devices, screen sizes, and resolutions unlike anything we’ve seen in the web industry to this point. That’s a full-time job.

But try not let it scare you. Remember the fear? This is one place where it can easily overwhelm you. “I don’t know enough” shouldn’t hold you back from launching a business — because no one ever knows enough. You’re best off if you can instead recognize that and focus on how to manage your lack of knowledge.

“I don’t know enough” shouldn’t hold you back from launching a business — because no one ever knows enough.

Before Sifter, I was a specialist. I needed to keep up with two or three high-level topics to stay current without being left behind. I had a few RSS subscriptions, and I kept up with a few topics on Twitter. It wasn’t easy, but wasn’t impossible either. Since starting Sifter, I’ve tried to stay current on every piece of our business from the technology stack to the business and marketing. As a sole founder, there’s no way I can build anything if I try to keep up with every little thing that has a chance of improving our product.

As an example, Sifter had about fifty lines of JavaScript when it launched. JavaScript wasn’t one of my strengths, so I focused elsewhere; it simply wasn’t feasible for me to build the application with all the advanced interactions that were becoming more common among web applications. Now that our vision and the application are more mature, we’ve begun adding more JavaScript where it makes sense, but we’re still mindful about where we add it.

Throughout all this, I’ve found that having a clear approach to new areas has helped me stay focused. Whether it’s a brand new area or just an area that’s new to me, this approach helps prevent me from feeling overwhelmed:

  1. Accept that you can’t know everything. It’s impossible to know everything and use every cutting-edge technology. This may be easier said than done when you’re constantly seeing others doing great new things, but it’s the only way you’ll get by. Use what you need — don’t try to be cutting edge just for the sake of it.
  2. Keep it on your radar. Just because you’re not using a technology or skill doesn’t mean you shouldn’t be at least vaguely aware of what’s happening around you. Keep your eyes and ears open through RSS and Twitter. Bookmark anything that you think might be useful for later, and then forget about it until you need it.
  3. Learn it when you need it. There’s not a lot of time for aimless exploration, but the good news is that if you need to use a technology that you haven’t used before, you can can learn it as you go. If you’ve been keeping an eye on things, you should have plenty of resources bookmarked so that you can dive right in.
  4. Be ready to leave your comfort zone. It may be tempting to avoid new things simply because they could slow you down and take you outside your comfort zone. But if you’re starting a business, you’re going to have to leave that comfort zone and learn new things. Mentally preparing yourself for that can make it less intimidating when the occasion arises.

It can be difficult to find time to keep up with the latest technology. It’s easy to get swept up in trying to stay current and to forget that the whole point is to create something. Instead of trying to know everything, you’re better off if can you focus on staying aware of what’s happening. Then, when the time is right and you come across advances that may be useful, you can learn as you build.

When you need to learn something, take the time to do it right — but if you don’t need it yet, file it away and move on. Worst case scenario: it’ll be there you when you need it. Best case scenario: newer technology could make it obsolete while being ten times easier to implement.

As a founder, your time is limited. You don’t want to be left behind, but you don’t want to spend all your time keeping up either. Running your own business will give you the flexibility to explore new technologies, but there’s no room to explore aimlessly. You should learn new technologies when you have a purpose and a reason to do so.

Continue to Chapter 9: Focusing & Executing


This is a chapter from the first edition of Starting + Sustaining, a book about bootstrapping a successful hosted web application business. The second edition, a massive update, will be out in Spring of 2017. You can subscribe here to be notified when it launches.

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