When You’re Never Satisfied With Yourself as an Entrepreneur

Dec 15, 2025

Understand the Psychology Behind Founder Pressure and How to Break the Cycle!

You finished all the tasks on your to-do list. You landed an important client. You worked really hard today. Still, that familiar pressure shows up. The internal voice whispers: It’s never enough. There’s always more to do. Do better.

And you might wonder, why does this cycle keep repeating? Let’s take a closer look at your brain and understand what’s really going on.

Is it like you’re afraid that if you acknowledge your achievements, you’ll be satisfied with yourself and stop putting in effort? Although you know you’re not going to stop, this is most probably the way your brain learned to get things done and improve, through the criticism you grew up hearing.

So now your brain is using the same familiar narrative, because this is the way it has been wired. More criticism, more shame feelings, more annoyance. For example, thinking things like “I should’ve done better,” “This isn’t enough,” or “People will expect more next time.” These feelings create the motivation to get rid of the discomfort by putting in extra effort. And here you get two reinforcements that keep you doing this again and again:

  1. The negative reinforcement: getting rid of the shame feelings temporarily 

  2. The positive/social reinforcement: being validated and celebrated for the great achievements

But here is the question: why get rid of something that is working

The answer is that at some point, your nervous system will break down with too much stress, because the more you succeed, the higher that bar will be raised, and with that, the volume of self-criticism behavior will increase in parallel, causing self-sabotage and losing control. 

Here, you feel that things are meaningless; hopelessness starts, as if your brain is trying to reevaluate the cost of the anxiety, the fear, and self-sabotage with the value of the outcomes. And the trick here is that most of the time, the big outcomes you are striving for are long-term, so your brain decides, “OK, that’s not worth it; I am going to give up.” And that shows in burnout, difficulties concentrating, frustration, feeling overwhelmed, too much sleep or lack of sleep, and sometimes being physically sick!

At this point, the self-image threat escalates because you don’t want to admit it or actually give up, even though your body has a different opinion and starts crashing down. This is exactly where Wellpreneur steps in, helping you remove the psychological and mental barriers standing in your way and guiding you through the steps you need to finally shift this pattern.

What to do:

  1. Changing the wiring between self-criticism and high performance is not a one-night job, yet it is very important to start with, because if it isn’t changed at some point, you will burn out.

How to do this: You might be surprised if I tell you how!

Start by writing your achievements daily for 2 months, and your job is to resist your brain when it tries to minimize the achievement you are trying to write and write it anyway. Also, with time, your nervous system will recognize that after 2 months of validating yourself, you didn’t stop achieving; actually, the opposite will happen, which is you will get more motivated, and your self-image will be aligned with your perspective of being a goal-oriented person. All we do here is rewiring and rebuilding the belief system and reward system.

  1. Being open-minded to change and resilient, because what your brain is using is the old programming that you have learned by modeling from your parents, teachers, and friends. Now the game has changed, so you need new narratives that serve you. If this point looks complicated, that means you need a specialist to give more assistance, and I am happy to help as an organisational psychologist or any other psychologist you feel comfortable with, because this is a lot of deep work that requires the observation of a third party.

  1. Reconnect with the reason you started in the first place, because whenever you are too focused on the outcomes and the external validation, the more you get stuck, and the more your nervous system will use helplessness and hopelessness to convince you to stop trying. Check the self-determination theory, or just send me a message, and I’ll share with you the test that will tell you what your top motivators are.

If you want to take serious action to do this, all you need is your willpower to change and a community to make commitment easier. And Wellpreneur is here for you. Send me a message, and I will share with you the challenge details. Or subscribe to get updates and more content like this.

Although we didn’t meet as you are reading from your screen, my name is Rania Albassoumi. I am an organisational psychologist and founder of Wellpreneur, and I have worked with thousands of entrepreneurs through accelerators and incubator programs, so I know what it takes to build something meaningful. And because it is not easy, I am committed to creating the first founder-first ecosystem to support founders like you from the inside out!