Founder Mental Health Pitfalls

Founder Mental Health Pitfalls


15 min read

This week, I chatted with Patrick Campbell about his exit of ProfitWell to Paddle for $200 million. One of the most mind-blowing things I experienced during that conversation was hearing Patrick tell me that he feels he needs to build something else to prove that this exit wasn’t just a fluke.

I did not expect that.

But I should have, because I feel the same way all the time. And the more founders I talk to —whatever stage of their journey they might be on— I hear them tell me the same story, too. Whether they just started out or sold their business for millions a few years ago, they still struggle with who they are, what they should be doing, and proving themselves and their worth.

This might not be the best advertisement for becoming an entrepreneur, and I know that. But it’s worth exploring anyway. Better to know what challenges you’ll be facing before you run into them at full speed.

Today, let’s talk about the many kinds of mental health pitfalls you might encounter throughout your entrepreneurial journey.

Balancing Parenting & Business

Being a self-reliant entrepreneur often requires a significant amount of time and energy, which can be challenging when you also have other responsibilities, such as being a partner or a parent. It’s already difficult to find a balance between your personal and professional lives when we have a 9-to-5, and it gets worse for founders. You feel like you are constantly juggling different priorities. This leads to feelings of stress, guilt, and overwhelm.

One of the main reasons this can be particularly problematic for entrepreneurs is that the success of your business often depends on your personal commitment and dedication — how long you’ll stick with a struggling project. You stretch yourself thin when you are giving your all to both your family and your business, and you may worry about letting one or the other down, even when you’re not overwhelmed.

It is crucial to set boundaries and prioritize your time — for both roles. This might involve setting aside specific times for work and family, delegating tasks, and seeking support from your partner, other family members, and the founder community at large. It can also be helpful to find ways to incorporate your family into your work, such as involving them in your business or setting up a home office that allows you to work while still being present for your family. I co-founded FeedbackPanda with my partner Danielle, and while it wasn’t always stress-free, her support and immense knowledge of our audience were invaluable.

We developed something we called “wearing our founder hat.” Whenever we were talking about business stuff during our non-business lives, we’d explicitly mention to each other that we were talking as our founder persona, not the partner. Drawing that line truly helped, and it’s likely something you can implement even if you’re not co-founding with family members.


No matter if you go at it alone or with a small team, you are constantly faced with decision-making, whether it’s deciding on a new product or service, choosing a marketing strategy, or making a hiring decision. It can be easy to get bogged down in the details and overthink every decision, which often leads to analysis paralysis. This can be frustrating and stressful, and it will prevent you from making progress in your business.

Time is a scarce resource. The longer you spend stuck in analysis paralysis, the less time you have to take action and move forward. Additionally, it can be hard to know when you have gathered enough information and it’s time to decide.

Set limits on the amount of time you spend analyzing each decision. I’ve heard founders literally using kitchen timers for this. This might involve placing a specific deadline for making a decision or enlisting the help of a mentor or trusted advisor to help you weigh the pros and cons. What matters is that there is a deadline — and a close one. You don’t have the time to form a committee. It can also be helpful to break large decisions down into smaller, more manageable steps and to remind yourself that it is okay to make mistakes and course correct along the way.


And those little mistakes can be stressful in aggregate, and it is common for entrepreneurs to cope with stress in unhealthy ways, such as drinking too much alcohol or using drugs, recreational or otherwise. While these behaviors may provide temporary relief, they ultimately do more harm than good and can lead to more serious problems, such as debilitating addiction.

The success of your business depends on your ability to think clearly and make sound decisions. Substance abuse will impair your judgment and lead to poor decision-making, which can negatively affect your business. Additionally, substance abuse can also damage your personal relationships and overall well-being — the two resources that are particularly good at keeping you grounded. That’s not something to willingly neglect.

Finding healthy ways to cope with stress is essential to alleviate this threat. This might involve seeking support from a therapist or counselor, finding ways to relax and unwind, such as through exercise or meditation, or talking to a trusted friend or family member about your feelings. You’ll find many founders who went through this themselves in the indie hacker community. Set limits on your use of alcohol or other substances, and seek help if you feel like you are struggling with addiction. Building a business is a way to create enduring wealth for generations to come. Don’t gamble that away with vodka.

Dealing with Failure

Throughout your journey, you will likely face various challenges and setbacks in your business. While dealing with these challenges can be frustrating and difficult, it is important to remember that not every problem has a clear solution. At times, you must accept that you cannot overcome some challenges, and it is vital to learn how to cope with failure and move forward.

Many of us have a strong desire to succeed and solve problems. That’s why we become founders: we want to make a difference. When faced with a challenge that we cannot overcome, it can be hard to accept that we have failed, and it can lead to feelings of frustration, disappointment, and even despair.

The way out of that pit of hopelessness is to develop a healthy mindset toward failure as early as possible. This might involve reframing your thinking and viewing failures as learning opportunities rather than personal shortcomings. Practice self-compassion and remind yourself that it is okay to make mistakes and that everyone experiences setbacks. Every founder who made it leaves a trail of mistakes along the way. Additionally, it can be helpful to seek support from others, such as a therapist or mentor, to help you navigate through difficult times. Again, the community, particularly those who build in public, can and will help you on this path. We have all been there and know how important it is to get used to making mistakes. The only mistake you should never make is ignoring your founder peers.

Not delegating can lead to anxiety

Here’s an open secret about me: I struggle with hiring. I think I can and should do everything myself. And there’s a pretty solid chance you feel the same way. You may feel like you have to do everything yourself to ensure that your business is successful. While it is essential to be involved in the day-to-day operations of your business, it is not healthy or sustainable to try to do everything on your own. This can lead to increased anxiety levels and burnout as you struggle to keep up with the demands of your business.

It can be hard to let go of control and trust others to handle important tasks. That’s what keeps me from seeking help most of the time: I worry that the people I pay will not do things correctly or that I won’t get the same level of quality if I delegate tasks. However, failing to delegate can lead to overwhelm and prevent you from focusing on the most critical tasks in your business.

We need to learn to delegate tasks and trust others to handle them. That’s just part of growing into the founder role. Identify tasks that can be delegated, find the right people to delegate to, and set clear expectations for their work. Having your processes well-documented really helps here. It can also be helpful to set limits on your workload and ensure you are taking breaks and taking care of yourself.

Burnout & Dreading Loss

Because if you don’t take care of your mental health, your mental health will take care of you. It’s so easy to get caught up in the hustle and grind and to push yourself too hard. Overworking yourself will eventually lead to burnout, which can have serious negative consequences for your physical and mental health, and, consequentially, for your business. You may feel exhausted, overwhelmed, and demotivated when burnt out, and it can be hard to find the energy and motivation to keep going.

You can’t maintain or grow a business if you’re unable to stay focused and motivated. Burnout will undermine your productivity and lead to poor decision-making, which then has negative consequences for the business. Also, burnout generates dread and anxiety about losing everything you have worked for, which makes things so much worse.

We have to practice self-care and set limits as founders. We need to take regular breaks, set boundaries, and find ways to relax and recharge. It can also be helpful to seek support from others, such as a mentor, health professionals, or entrepreneurial peers, to help you navigate difficult times. I’ve been through business-related burnout twice, and it has been the community that helped me recuperate, reset, and reframe.

Navigating imposter syndrome when others appear successful

Where burnout is the nuclear explosion, imposter syndrome is the nagging electrostatic shock you get every time you sit down on your couch. Imposter syndrome —the tendency to think you’re unqualified for your work— is a common experience among entrepreneurs. It can be particularly challenging when you feel like everyone around you seems to have things figured out perfectly. Imposter syndrome is characterized by feelings of self-doubt, insecurity, and fear that you are not as competent as others perceive you to be. It can lead to feelings of inadequacy and, when acted upon, will prevent you from taking risks and pursuing your goals.

Self-doubt undermines your confidence and leads to poor decision-making. It can also make it hard to build a successful business, as it prevents you from taking rigorous action and taking risks. Additionally, imposter syndrome can make you feel isolated, as you may think you are the only one struggling with these feelings.

What you need is a healthy mindset to challenge your negative thoughts. To build your confidence and self-esteem, you must remind yourself that everyone makes mistakes and that it is okay to ask for help. Follow those who build in public, and you’ll see them struggle with the same problems. Most founders feel imposter syndrome. So feel it, observe it, and ignore it. When you’re breaking new ground, some part of your brain will always be afraid. But you don’t need to listen to it.

Second-guessing decisions and dealing with incomplete data

Founders are constantly faced with decision-making, and it can be easy to second-guess yourself and doubt your decisions. This can be particularly challenging when working with incomplete data or dealing with nebulous perspectives — as every entrepreneur does. Nothing is written in stone, and there are often no previous examples or guidelines to follow. It can be hard to know if you are making the right decision, and you might worry that you are missing something important.

Again, it’s all about time management. The longer you second-guess yourself, the less time you have to take action and move forward. Additionally, second-guessing yourself can undermine your confidence and lead to poor decision-making. It’s applied imposter syndrome.

One of the most profound skills that you, as a founder, must learn is the ability to make decisions with incomplete data. This skill can be challenging to master, especially in the early stages of starting a business. It requires you to weigh the facts and make an informed decision, despite not having all the information to hand. It is a skill that will serve you well throughout your career, helping you make sound decisions despite uncertainty. It is okay to make mistakes. Everyone makes decisions with incomplete data when they’re building a business that has never existed before.

Underestimating and Judging Yourself

And running such a business can be a lot of work. It can be easy to underestimate the time and energy it will take to build something that works “well enough.” This can be particularly challenging when you are starting out and are not sure what to expect. It can be hard to know when you have reached a point where your product or service is good enough to launch or when it is time to pivot. If you’re a perfectionist, this is particularly hard.

If you continue to pour time and energy into a product or service that is not working, you will waste valuable resources and miss out on other opportunities. Underestimating the amount of work required can lead to feelings of frustration and overwhelm as you struggle to keep up with the demands of your business. Burnout is lurking around the corner.

What helps me with that is to assess my progress regularly. When I see how far I have come already, I have an easier time cutting my losses on things that don’t work. After all, there are so many things that did work! It’s hard to recognize when it is time to pivot or move on, but it gets easier over time. Being open to new opportunities instead of tunnel-visioning on your choices helps a lot with that.

Debilitating Shiny Object Syndrome

But you can also take this approach way too far.

As an entrepreneur surrounded by other founders, it can be easy to get caught up in the latest technologies and frameworks and constantly chase after the newest and most innovative ideas. While staying up-to-date and being open to these opportunities is important, finding a balance and committing to a course of action are equally essential. “Shiny object syndrome” can lead to wasted time and resources as you constantly switch from one idea to the next, preventing you from making real progress in your business.

Learning to filter out the noise and focusing on what is most important is critical here. It can be tempting to chase after every new idea or technology, but this will lead to confusion and indecision. Additionally, constantly switching focus can make it hard to build momentum and make real progress. Switching cost isn’t just money — it’s your attention and valuable time that you pay here.

That’s why you have to start with and constantly express a clear vision and mission for your business. From that, set clear goals and priorities. Surround yourself with supportive people who can help you stay focused and remind you of your long-term goals. Evaluate new opportunities, sure, but don’t follow the urge to completely rebuild everything just because a new framework promises a 2% improvement. The best tech stack is the one you already know.

Feeling guilty for taking a break

If you ever feel guilty for taking a break or feel like you are not doing enough to grow your business, you’re not alone. Everyone wants to be dedicated and work hard, which often translates into long hours and grinding away into the night. But you have to take care of yourself and make time for rest. Ignoring your own needs will lead to burnout and destroy your business.

It is so hard to let go of the mindset that you must constantly work to be successful. The “grindset” is so pervasive in the entrepreneurial community. “Hustle porn” is what they call it. You may feel like you are letting your business down if you take a break, or you may worry that you will fall behind if you step away from your work. But taking breaks is essential for maintaining your energy and focus, and it will actually help you be more productive in the long run.

There’s only one way out: prioritize your well-being. Set aside specific times for relaxation, and find ways to recharge. Taking care of yourself is essential for the long-term success of your business. Take the break, or the break takes you.

Underwhelming Sales

Finally, let’s talk about inflated expectations. It can be difficult to deal with underwhelming sales, particularly in the beginning. It’s frustrating and disheartening when you’re putting in a lot of effort and not seeing the results you were hoping for. Sure, we all need to be persistent and keep working towards our goals, but we have to be realistic and adjust our approach if needed.

Low sales can lead to financial stress and make it difficult to sustain your business. Knowing how to improve sales and identify the root causes of low conversion rates can be tricky. You might have self-doubt and insecurity as you worry that you are not cut out for entrepreneurship.

We’ve all been there. In fact, we’ve never left. Most founders feel that sales aren’t “good enough.” What helps me is the shared commiseration of the founder community. Especially by building in public and following those who do the same, I find solace that just because I had high hopes doesn’t mean the numbers are wrong. It’s all in my mind, most of the time. Of course, there are issues where I might need to change my pricing or sales approach, but more often than not, it’s just the collision of my hopes with reality.

All I can do is stay positive and remind myself that it’s normal to experience setbacks and that every business has its ups and downs.

Starting and running a business can be a challenging and rewarding experience, but it is not without struggles. It can be hard to balance the demands of your business with the needs of your personal life, and it can be easy to get stuck in analysis paralysis or to deal with stress in unhealthy ways. It can also be difficult to accept that you cannot solve some challenges and to cope with failure, and it can be hard to know when to delegate tasks or when to take a break. These mental health challenges are common among entrepreneurs, and it is important to remember that you are not alone in facing them.

It is important to remember that every entrepreneur faces challenges, and it is normal to feel overwhelmed or uncertain sometimes. The most successful entrepreneurs are those who can navigate these challenges and find ways to cope with the mental health problems that come with being self-reliant. By developing a healthy mindset, seeking support from others, and taking care of yourself, you can overcome these challenges and build a successful business that aligns with your values and goals.

So if you are feeling overwhelmed or uncertain as an entrepreneur, remember that it is okay to ask for help and take a break when needed. Surround yourself with supportive people who can help you navigate through difficult times, and remember that every challenge is an opportunity to learn and grow. With the right mindset and support, you can overcome any obstacle and build a successful business that brings you happiness and fulfillment.

The post Founder Mental Health Pitfalls appeared first on The Bootstrapped Founder.