The Culture Shock Of Working For Yourself

At the end of 2016, I crunched some numbers and realized I could quit my job and have a 3 year runway. I decided to take a gamble on myself and try my hand at entrepreneurship. There's a lot that's hard and different about starting your own thing, but I'm going to focus on one right now: the approach to work.

I tried what many people try. I took the process that I had used for work and I tried to apply it when I started building my own software.

That means coming up with a plan. Brainstorm some stuff. Talk to some people for feedback. Determine the priorities. Stick to those priorities and ignore distractions. It all sounds good. If you're quitting your job, you want to take your business seriously. Replicating your work processes is an indicator that you are taking the business seriously.

These days, I embrace distractions. I encourage anyone who tries their hand at entrepreneurship to embrace distractions.

Working for yourself is unlike working at a job. No one is setting goals for you. No one is evaluating your performance. You don't have an existing product/business to use as a baseline. Most importantly, you don't have a team to work with. It is just you (and your dog, who does not contribute as much as you'd like).

The beginning is exciting. That is when you're the most motivated. The problem is that all honeymoon periods end and entrerpreneurship is no different. There's no real structure as an entrepreneur. You set your own goals. You evaluate your own performance. Your product can be anything because it doesn't exist yet. You have no team to talk through your decisions with. The result when the excitement dies is a whole lot of procrastination.

You can always lie to yourself about that procrastination too. Maybe you spend more time organizing your office since that's productive. Maybe you spend more time networking or on social media as "part of the business". Maybe you just make another cup of coffee because coffee fuels productivity. Or you take one more break so that you can be refreshed.

Doesn't embracing distraction make procrastinating worse? Aren't they the same thing?

Procrastination is doing something that has zero chance of moving the needle for your business.

A distraction can be an experiment that is unlikely to move the needle for your business, but the chance is not zero. An example of this is getting an idea and building a quick prototype. It may have nothing to do with your defined list of priorities, but it was fun and you wanted to do it.

That kind of behavior is unacceptable when you're at a job where promises have been made to customers, but absolutely essential when working for yourself and you have no customers yet. I have two reasons for this: momentum and product research.

Let's start with momentum. Procrastination starts because starting something from scratch is a real slog. You can build all sorts of things that no one will care about. They will even tell you they care about it and then not use it. With a job, what you work on will likely get used because there's already a baseline product. Even if it doesn't, you have a team and an organization that will provide meaningful feedback on the work. You have information to go on to take the next steps.

In entrepreneurship, you rarely get good feedback. Most people, even people who don't know you, don't want to say bad things about the thing you've built. They just won't use it. That leaves you nothing to go on to improve. You just keep going and trying until something clicks, but that is way easier said than done.

I once heard one of the co-founders of Indie Hackers say that startups don't fail because you ran out of money or were beaten to market by a competitor. Startups fail when you quit. I think this applies to most businesses. Not knowing how to move forward is incredibly demoralizing. That increases procrastination which in turn makes you more demoralized. The end result is a high probability of quitting.

Let's go back to a common reason why people start entrepreneurship: they're excited about an idea. What is important is maintaining that excitement while the slog tries to kill it at the same time. Working on random ideas that pop into your head may not be conducive to direct business success, but it can keep you in the game. It can keep you excited about your overall business and it keeps your working on it rather than looking for random nonsense to procrastinate on. Working on random ideas can stop you from quitting.

Also, while you will have to get organized to build a cohesive product eventually, you're unlikely to know what a useful product is at first. Your initial idea is probably unviable. Your initial conversations with people are probably misleading for the same reason it is hard to get good feedback. User research is often talked about as a precursor to writing code, but having working software in front of people is the best experiment you can run.

Building random ideas in your head gives you an avenue to run those experiments. It gives you the opportunity to discover things you may have not even considered with your original plan. You'll eventually need a list of priorities to build a viable product, but you don't have to rush into that. It makes sense to experiment at first and do real research.

This is just one of the many issues that occur when working for yourself versus having a job, but I think it is the most impactful difference. It's too easy to focus on the excitement and hard to imagine a time when that excitement has died down. It's hard to consider maintaining excitement as a valuable productive thing for running a business when there are so many things that seem more important. Yet, doing so can mean the difference between persevering through the slog or quitting.