Real and Imaginary Responsibilities of a Bootstrapped Founder

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This article is part of The Survival Stage section of 📕 Zero to Sold: The Bootstrapper’s Compendium.

As a founder, you will encounter many expectations. Founders have to have a mission. They have to care about their customers genuinely. A great founder is a leader, a visionary, an expert.

Sometimes you just want to be you — the entrepreneur who had a good idea for a business and then worked on it diligently. You don’t need to be a hero. You just want to run your business.

And still, you feel like you’re not meeting expectations. You feel like you could do more to help your customers. Give more back to your community. Others know so much more about your industry. Everyone else is doing things differently.

Welcome to the world of imaginary responsibilities.

Every founder feels them. They creep into your mind when you see yet another business that is doing better than yours while browsing Twitter.

They invade your dreams because you listened to that podcast with the super-successful guest just before bed. They had so much fun laughing and talking about their successes, and you’re sitting there, thinking you’re just an imposter.

I have been there too. And I have learned how to climb out of these traps that I fell into many times.

There are a few main themes that come up once in a while. Learn to recognize them, learn to focus on what is real, and ignore the imaginary. Your mental health will improve significantly.


Perfectionism

You have been building this cool new feature. It works on your development system, and it will be impressive once you release it. But the user interface can still use some work.

You know that a few of your more technically illiterate users have had trouble with complicated interfaces, and you want to make sure that every single of your customers gets some value out of the system. So you spend another week polishing the UI.

Then, you notice that the documentation you wrote for the feature might use a few more clarifying videos. So you spend another week creating walkthrough videos for every single way customers might use the product.

Then, you notice something else. And another thing. You end up never releasing the feature.

Welcome to perfectionism. It will keep you from achieving your goals. 

“I have to build the perfect business.”

The perfect business doesn’t exist. Any business is a dynamic enterprise, a thing that you do, not a thing you have. Nothing in your business will ever be perfect, as there is always room for improvement. 

Rephrase this into “I want to build a sustainable business. I want to live a good life, providing a solution that will help people.” Set your goals to something you can control, not some platonic ideal of a business. A working product does not have to be perfect. It just has to work enough to be useful.

Don’t stress. Approach your business with the Pareto principle, the rule of 80/20: the last 20% of your work will take up 80% of the time. Save yourself from wasting your time like that. Get 80% of it done, and deal with the rest when (and only if) it is needed.

Focus on long-term goals and create traction, both within your own life and with your market. Every action you take needs to have a real impact on whom you want to serve. Don’t focus on details that only a few customers may ever see. Work on things that lift all of your customers at the same time. 

Usually, the most impactful things are also the hardest things to do. Start with those things. Don’t take the low-hanging fruit. It is usually the first thing your competitors will also pick. Go for the things they fear to tackle. Do this often. That is how you will stay ahead even if things don’t seem perfect. 

“I have to create the ultimate solution for all the problems my customers have.”

If there were all-encompassing solutions, we would only drive one car. We would eat one kind of cheese and use one type of shampoo. But we don’t. We have choices because we have different priorities, and excellent products take that into account. 

Rephrase this into “I want to provide value to my customers that makes their lives easier.” They don’t expect you to solve all of their problems. A swiss-army-knife is great, but you don’t see mechanics use it to repair cars, or chefs to filet a fish. Special tasks need special tools, and that is true for almost everything people do, both in their personal and professional lives.

Do one thing really well. Focus on the critical problem that your customers have. They may have additional issues, but you should focus on the most critical one. Once that is solved, you can look into other problems. Not before.

The more you’re spread out with your products, the less you will impact the lives of your customers. You will need to make choices about which product deserves your attention, starving all the others. Particularly in the beginning, focus on one specific problem and solve that problem alone. Your attention to detail will be a differentiator to all those Swiss-army-knives that look great but are ultimately disappointing.

Impostor Syndrome

You’ve been thinking a lot about your bootstrapped business. You did the research, built a prototype, talked to prospective customers, and worked their feedback into your MVP.

Then, one day, you read an article about your target industry, and you stop reading in the middle of the page. You know you did all this research, but you feel like you don’t have any idea what is going on in the industry. There is so much more you need to learn before you can start your business.

You definitely need to read more books. There are so many podcasts you still need to listen to. You end up learning forever and never start your business.

Welcome to impostor syndrome. It will keep you from achieving your goals. 

“I feel like I’m not good enough to create something great.”

In a time of life-long learning, we’ll never be finished learning. So we might just as well start creating things sooner than later. Just like learning never ends, neither does perfecting the product. So when you start, it might not be great. But it is something. And that alone sets you apart.

Rephrase this into “I can start with something that works.” The fact that you are working on a solution to someone’s problem already sets you apart from everyone else. Most people don’t even start. They are caught up in the belief that if they learn just one more thing, they will be ready. They never are.

Any improvement over the status quo is good. Don’t let the VC siren calls of “it needs to be an order of magnitude better” lull you into thinking that if you don’t disrupt the whole industry, you won’t be adding value. Value-add starts with the smallest things. If you add enough value enough times, you will make a significant impact on the lives of your customers. 

Start with what you know. Create something that you think is useful. Then go out and talk to the customers. Get their feedback and adjust. Repeat until you have found the solution. Repeat this until you have made something great.

“I have to be the most knowledgeable expert in the domain.”

Sometimes, you look at your audience and feel intimidated. Here are people who have worked in their positions for decades. They know the ins and outs of their business, and they have seen many vendors come and go. You feel this fear that if you are not just as much an expert as they are, they won’t even look at you.

Rephrase this into “I need to know enough to help.” Expertise takes time, and it takes experience. You can’t read up on experience. You will have to get it yourself by working for your customers. 

You will become an expert by trying. If you succeed, that is great. You have a fantastic business, and your life will be improved significantly. If your business fails, you will now be an expert in the field. You know the size if the market. You have developed a sense of where the problems are, what solutions you can create, and how to talk to people in the industry. You can start a new company or consult people who do. It is a win-win situation.

Expertise comes from experience. Do the work. Spend the time. There is no better place to learn than right in the thick of things. Jump into the deep end and keep swimming. You will learn so much in such a short amount of time.

Most importantly: you are not a fraud. Real impostors don’t suffer from impostor syndrome.

Cargo-Culting.

You read that bootstrapped founders do things a certain way. They never take funding, so you swear you will never take funding. They talk to customers at all times, so you take every opportunity to speak to your customers at all times. This is what bootstrappers do. They iterate quickly on their product, so you try and release a new feature every few days. They go to conferences, so you fly all across the world to talk to your peers. You notice that everyone seems to be crushing it. You redouble your efforts, and you spend more time on your business. This is what bootstrappers do. You have not seen daylight for a few weeks, your children only see you hunched over your laptop, and you haven’t called your parents in over three months. You keep doing this until you burn out. 

Welcome to cargo-culting. It will keep you from achieving your goals. 

“I have to do everything by myself because I’m a solopreneur, and that is what they do.”

The term solopreneur is aspirational for many people who want to start a business — keeping all the profits! Never having to explain yourself! Full control over every aspect of the company! And then reality hits, you run into brick walls, your mental health deteriorates. Your energy levels are depleted. You don’t enjoy work anymore. That’s not where you want to end up.

Reframe this as “I can get people to join my cause when I am overwhelmed.” Humans love to join things that have a purpose. People want to be part of missions, and they want to help. Don’t think you have to do everything alone. You won’t, and you can’t. At some point, you will need other people.

Delegating work to others can free you up in many ways. It’s not just about your time. It is about your focus and your potential. Any task you don’t want to do is a task that keeps you from taking care of something that you want to accomplish. Interruptions will slow you down and deter you from reaching your goals.

We waited much too long with hiring people at FeedbackPanda. I was taking care of development and customer service. Incoming help requests constantly interrupted my product work. I still get PTSD from the Intercom notification sound that indicated a new customer service conversation. The moment we hired a customer support person, and they took that workload off me, my head was clear again within days. I could focus again. And it turns out that other people are better at customer service than I am. They would keep calm and help where I frantically apologized and overwhelmed customers with technical details. Delegating will make the experience better for you and your customers.

“I have to risk burnout because successful people work hard.”

Hustle porn is everywhere. People show off their accomplishments on social media and in the founder communities. Businesses hit their goals and milestones left, right, and center. Everyone is crushing it, and rarely do you hear of anyone struggling. But you struggle all the time. Is there something wrong with you? No one else seems to have these issues.

Reframe this as “I have to take care of my mental health.” A business with a continually struggling founder struggles itself eventually. There will be ups, and there will be downs. People don’t usually talk about the bad parts. Only recently have I seen founders share their tales of struggle and defeat in public spaces. It is a great start, but the stories of glory and success still prevail.

Burnout is not a badge of honor. It is a medical condition. It’s a state you don’t ever want to be in. When you experience burnout, you lose your drive. You are exhausted; you lose the joy of your work. Your performance suffers. It takes a long time to get out of that state. 

I had experienced burnout twice before, once when I was working for a VC-funded company in Silicon Valley and then later during growing FeedbackPanda. In both cases, it took me a long time to recover. Finding the motivation to work is hard when the sound of an email triggers a mild panic attack. That is not a good place for a founder.

Working hard is not working long hours. You can be productive by working smarter. Delegate tasks that irritate you to people who love doing them. Automate away things that don’t need your direct involvement. Start with your customer service [customer service link]. Then move to other repetitive tasks. Repeat until your workload is manageable.


Here is the thing about responsibilities: they are all in your mind. Sure, you may have contracts and obligations, but what you focus your attention on is determined by your thoughts. The expectations you set are all in your head. Once you become aware that the only thing standing in the way of your success if yourself, it becomes so much easier.

Don’t fall for being perfect. Don’t doubt yourself. Don’t do things because that is the way things are done. 

Just be your authentic self, ready, and eager to learn. That is an excellent foundation for a sustainable business that helps real people with their real problems.

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