Seven Steps to Overcome Self-doubt Towards a Successful Startup Leadership Career

16 min readSep 28, 2023

As a startup top or C-level leader (CXO), there are many uncertainties and challenges you have to deal with in this role, especially if you have lots of corporate experience. The scale and maturity of an established, profitable multinational corporation spoils executives with a rich pool of specialized experts, stretched timelines, and large budgets. It deprives a CXO of learning how to build a company incrementally, being comfortable with uncertainty in decision-making, and being hands-on instead of just delegating work. But the positive side is that their corporate experience gives them an understanding of how a mature organization works, including its dysfunctions. So, the challenge for them is to agree with the CEO and their peers on how the future looks like and reverse engineer the building block of their startup, especially during the scale-up phase. The insecurity that this uncertainty brings will make you feel like you’re pretending to be an expert, especially if, at times, you have to make decisions based on calculated guesses and just gut feeling. This feeling is also referred to as Imposter Syndrome (IS). Being comfortable with taking a product and building scalable company operations around it requires a mindset change from your corporate experience or what you learned in school, which I cover in more detail in my book Skill-up As You Scale-up. I discuss the SAUS (Skill-up As You Scale-up) principles in the book, which aims at shifting your mindset to be startup-ready and to improve your chances of success in your new CXO role, especially if you are working in outside developed startup ecosystems like Silicon Valley (USA) or London.

Imposter Syndrome (IS) is when you feel phony when you expose your work to the public. The intensity of IS is assumed to be high in intelligent individuals. Assuming you’re one of these individuals who suffer from IS, to overcome its barriers, you need to meet three criteria: first, acknowledge that you have IS; secondly, that there’s a solution (or multiple solutions) for it, third, that the solutions available will help you eliminate the symptoms and turn it into an advantage.

When thinking about IS, some of the questions that come to mind include: what’s the right solution? Should you fight it or embrace it? What does embracing it look like?

This article focuses on what IS is, how it affects you as a CXO, and how you can turn it into an advantage, especially if you’re part of a startup ecosystem that’s situated outside developed startup ecosystems such as Silicon Valley (USA), London, or Shenzhen. I’ll also be sharing my experience based on my successes and failures.

What is Imposter Syndrome and Why Do I need to know about it?

IS is a psychological term that refers to the feeling that a person fears being seen as a fraud. This feeling stems from doubt about their abilities, skills, and achievements. So they feel as if they don’t deserve to succeed. It usually leads to depression, anxiety, and burnout. In extreme cases, it turns from just doubt into self-deception, which gradually manifests into reality, focusing on what they haven’t done or are incapable of doing, supported by a growing number of examples.

Studies have shown that there are two primary roots to having it. The first is living amongst siblings labeled as intelligent, which overshadows the person with imposter syndrome. The second is being always praised for perfection, which adds pressure due to the high expectations.

Even though the word “syndrome” refers to a disorder or a disease, IS isn’t categorized as a disease because it doesn’t have apparent symptoms or causes. The first time IS surfaced publicly was in 1978 by psychologists Pauline R. Clance and Suzanne A. Imes, who published a paper referring to IS as the Imposter Phenomenon. They used the word “Phenomenon” to clarify that this is not a disorder.

The levels might vary from one person to another based on many factors such as age, experience, education level, culture, personality, history dealing with bullying, and core values. The complexity increases when an intelligent person goes from self-doubt to a sense of self-deception. This is where self-sabotage takes place by re-enforcing their sense of phoniness by focusing on their few weaknesses instead of their achievements.

For example, Leila (not her real name) has graduated from two of the best universities in the UK and has a track record of promotions with multiple employers after fifteen years. Her ex-colleagues kept coming back to her for advice many years after she left those organizations. However, her self-deception kept pushing her into a spiraling reinforcement of self-doubt backed by assumed evidence, and she started getting into a depression to the level that she got fired for not performing due. Her depression and stress triggered a speech impediment where she was stuttering. This is an extreme case that took Leila to the dark side.

There’s a positive alternative where Leila could follow new routines, such as speaking to people with similar situations, speaking to a mentor, or starting a board or a journal where she lists her achievements. She could have used many solutions if she knew what IS is and how to deal with it and turn it into an advantage. IS can fuel your commitment to surpass the competition in a domain where the barriers to entry are higher for the average person. So this means it’s not bad to have IS, even if it’s spiced up with self-deception. So what practices and routines can we follow to ensure you unlock this superpower and bend the rules to turn IS into your fuel to stay focused?

All of this makes me wonder how many great product ideas or inventions we can’t see today because of IS. How many startups went bankrupt due to IS trigger self-deception in the head of the CEO or the founder? How many CXOs lose confidence due to resistance to change?

Many Western public figures are opening up to talk about their challenge with IS. Tom Hanks, a famous American Actor who starred in movies such as Cast Away and Forrest Gump, was asked in an interview if he had IS during the shooting of the movie “Road to Perdition,” and Tom’s response was, “Oh, absolutely.” He described later how he had to lift himself up to get through it. He was nominated for Best Actor in a Leading Role.

Perception between cultures like the Middle East, India, or Africa

IS isn’t commonly accepted as a phenomenon in many cultures, such as the Middle East, India, and Africa. Many still see it as an excuse to avoid hard work or justify a lack of delivery and perseverance, which is a valid point of view. Many of us grew up in environments where in countries where the opportunities are limited, and the competition is high. This pushes everyone to work harder than their competition. You can see this also amongst people who immigrate to developed economies as well.

I had a few chats with entrepreneurs and CXOs on the subject, and the views were diverse. For many, it’s like talking about making crucial decisions using horoscopes, which is fun but not to be taken seriously. At the risk of sounding ignorant, I observed that people educated in developed economies are more empathetic to the concept of IS than those educated in emerging economies like the Middle East. Their perception of IS is influenced by factors such as their core values, culture, lifestyle, and income class.

That’s why I believe both have valid points and examples to prove their point of view.

So what do you do if you believe you have IS and live in a culture that doesn’t openly accept it? This situation could be limiting. If you follow the advice that tells you to “speak to your line manager,” then you’re taking a risk where this could backfire. Your line manager could label you as lazy or delusional, which will make it worse because it will reinforce your doubts and turn you into a victim of workplace bullying or a state of self-deception. In a large corporation, you could go by with such a burden for many years, living a resentful life doing what you’re asked and not daring to ask for more or challenge anyone. However, in a senior role at a start-up or a scale-up, you don’t have such a luxury, allowing such energy to pollute your workplace and spread seeds of doubt in your initiatives. If you go quiet and let the doubt take over, you’ll be feeding into a rumor that will eventually become a fact, and you could lose your job and reputation in the process.

“Repeat a lie often enough, and it becomes the truth.” Nazi Joseph Goebbels

This is known in psychology as the Illusory Truth Effect, where if misinformation is repeated many times, it will become the truth. The victims include people with high levels of intelligence. For example, many of us heard that vitamin C protects us from getting cold and flu, while in reality, there’s no scientific evidence proving that vitamin C is an anti-flu remedy. If you pay attention, you’ll notice that you can find examples used by politicians, bullies in school, old folk stories, journalists, influencer personalities, and marketing experts. That means you’ll be pressured to follow the general perception without even knowing that a bias got triggered and is doing its magic in the background.

Another example of a lie that was considered an inspirational quote catching momentum was a quote from the famous Indian businessman Ratan Tata, who says, “I don’t believe in making the right decisions. I take decisions and then make them right,” going viral all over social media and the internet for years and then in an interview at an event in France in June 2015, he denied saying it. He explained that the quote associated with him was never a statement or a philosophy he was following. Many of us don’t have access to platforms that could help us set people straight, and even if we did, no evidence would convince anyone a hundred percent that what you’re saying is the truth.

The Startup Leader’s Mindset

As a start-up CXO, you always need to be decisive. In reality, it is impossible to be decisive a hundred percent of the time, especially in a startup environment that’s filled with uncertainty. So, it’s all about getting more hits than misses when you decide to give you a net gain and success at the end of each year or quarter.

There are many ways to deal with such doubts if you understand the underlying cause of it. The way I minimize this doubt, which is fed by the fear of failure, is by listing a project brief for every project I work on. The brief includes the purpose or goal, the objectives, deliverables, risks, and success factors. This helps me have a comprehensive view of what could go wrong and how fast I can fix things if they go wrong. That document becomes my communication tool with all the other leaders and stakeholders. It doesn’t matter if IS is real or not. As long as you are aware of such feelings and you’re focused on the objectives at hand, your brain will desensitize that fear of being seen as phony, which will free you up to focus on doing your best.

Some of the best athletes, such as Lebron James, the basketball player, meditate to deal with performance anxiety and imposter syndrome about winning before a match to get their brains familiar with the details of the situation. You could call it the “power of manifestation,” or as the actor Jim Carrey puts it in one of his speeches, “…releasing a thought into the universe and letting it know what you want.” It works to condition your brain to remain focused on the goal and to desensitize yourself to the feeling of doubt. Also, when you’re in survival mode, you don’t have time to think about anything other than doing your best at that moment. It’s the same with a CXO role in a startup.

My Experience With IS

From experience, I’m at peace with the idea that I’ll never get rid of my IS, and I have learned to live with it. I imagine it as a wave that has to keep fluctuating, creating a current in my performance and personality. When I’m filled with doubt, I work hard to make sure I do my best within the available time and resources, and once the outcome gets me acknowledgments and praises for the excellent work I’ve done, I’ll be satisfied for a short period, and then another cycle starts. I don’t know if this is the best way to look at it. However, it’s the best way that works for me. As an example, as I have been writing my first book titled Skill-up As You Scale-up, I was hesitant to share the book details with my professional circle until I was comfortable that the tools and frameworks I developed were stress tested with my projects, and then later used by the companies I’ve been mentoring or coaching. So, I started working on it in early 2020, to the point where the first draft of the manuscript was completed in 2023. Could I have finished it earlier? Yes, absolutely; however, I would have been less comfortable with it. I still haven’t released it yet, so I don’t know what the outcome will be. However, I’ve been receiving positive feedback and recommendations from my professional circle, which has been helpful.

How To Turn It Around

Embracing IS as a force that will help you stress-test and refine your deliverables, whether a proposal or product, can give you a competitive advantage. Embracing the uncertainty it brings will enable you to improve your critical thinking skills. It will also keep you humble at all times, which will balance the arrogance your success brings your way. Also, embracing your IS means that you will listen more than you speak and take thoughtful actions. Most of your colleagues and industry peers will perceive you as mature and collected. However, some will see your hesitation and calmness as a sign of weakness, and your collectedness from reacting and the results you deliver will prove them otherwise.

When thinking of solutions, most of us will immediately think of actions we need to take as antidotes to counteract the root cause to eliminate the symptoms and pain. You can find many resources that will give you advice to be open, use a coach, use positive self-talk, or keep a journal, which are useful. However, like antibiotics, you eliminate both good and bad bacteria when you take the pills. It’s the same with IS, where you’ll eliminate the benefits of IS.

Inspired by the philosophy of jiu-jitsu, an ancient Japanese Martial Art, you learn how to manipulate the opponent’s force attacking you instead of confronting it head-on. Applying the same philosophy taught me how to be at peace with it and avoid the trap of perfectionism. If you search on the net for the keyword “embracing imposter syndrome, you’ll get some good resources that will teach you how to follow.

So, how do you change IS from a toxic thought pattern that could cause performance paralysis into a fuel that helps you strive for more? The following are some suggestions I have tested and worked for me, but there’s no magic pill. So, you must go through your journey to see what works best for you. Your personality will also evolve, so what works today might not work a year from now.

1. Find the right people to open up to about your IS challenges:

It’s important to talk about it with people you trust who share the same problem. Whether you’re using a coach, a mentor, or a friend to help you do sanity checks on situations where you feel IS is playing a role. Do not be too open about having IS with people who are not open to the idea. If you want to talk about it with your line manager, you could test them by sharing an article you read or asking them what they think. That could give you an idea if speaking to them and taking their advice would be helpful.

2. Focus on doing your best instead of just focusing on winning or failing:

Using a journal or walking meditation could help you focus on conditioning your mind to focus on the success factors, the deliverables, and trying your best and accepting the fact that things will go wrong and you have to try your best to fix them along the way. The more you practice or prepare, the better the outcome will be.

3. Focus on small improvements that lead up to the goal:

Your abilities really improve through the experience cycles you go through, not in years of experience as most people assume when they showcase their capabilities to employers or customers. When I talk about the experience cycle, I refer to the little projects you can have that take you closer to a deliverable or an object you aim for. To stay disciplined working on as many little projects as possible, you need to have clarity on what the goal is and what deliverables you need to deliver so you can achieve those objectives. The easiest way to have the discipline is to put it in your calendar and show up. If you need to restore a car, then go to the garage and get the tools ready. If you want to complete a task as part of your mobile app, go to your desk or the place where you usually work. Co-working sessions with peers, even if your work isn’t related, can help you build habits and progress incrementally. There are many more tricks to overcome procrastination. If you want to improve a skill, following a project-oriented approach with a daily time booked for it will help you improve over time. For example, I was struggling with improving my piano playing skills for a few years. Once, I decided to book 15 minutes a day to practice my music reading and playing skills improved significantly. The routine enabled me to overcome procrastination. If you’re running against tight timelines, borrow the brainpower of your colleagues and others in your network by adding them to your network or asking them for help. This will help you become more confident and focused on the outcome.

“Don’t confuse movement with progress because you can run in place and not get anything done…” Denzel Washington, American Actor

4. Allow yourself to make mistakes and learn from them:

You can run small experiments, which lowers the risk and time invested to prepare you for the big goal you’re trying to achieve. Setting very high standards is good as long as it doesn’t hinder your progress. The Japanese philosophy of “Wabi-Sabi” refers to embracing imperfection as perfection and that nothing is meant to be perfect. We see this in nature. You’ll never see a perfectly shaped apple or mountain, and there will always be rough edges or marks that distinguish it. So, when speaking or presenting, be natural and genuine.

5. Journal your achievements and review them regularly:

When you feel doubtful, take time to journal your progress over time toward your goals and what you have achieved so far. On my calendar, I refer to them as plain “Planning Time,” where I review what I have achieved and what I need to start doing, stop doing, and continue doing. This helps me gain more clarity and maintain my focus on what matters, which I believe helps me with my IS in the long run.

6. Prepare by rehearsing and practicing:

The more you practice a speech or a pitch, the better you’ll get at it and the more comfortable you’ll become with the content. Record yourself and review it. Seek feedback from people you trust. Expect criticism and look at them as constructive feedback.

“Fortune favors the prepared mind” Louis Pasteur, French Scientist

7. Start small even when you’re not ready:

This is my biggest challenge. For some things, it feels that the right time is never there. For example, I had the idea for my book for many years, but kept seeing the gaps of what I need to learn and test over and over. Today, I believe I was right, at the beginning, but somewhere in between, IS kicked in and I started rationalizing that I need to prepare. Four years ago, a conversation with a friend made me question myself on whether I’m procrastinating or really need to complete my research first. I believe, I could’ve started earlier and kept building it publically before feeling ready and completing my research. There’s no absolute right or wrong approaches, but there’s an optimal for you for that moment factoring all the variables around you.

I have been following activities and philosophies for many years, some that have worked for me, and some that didn’t. More things can be done to help me control my IS. I’ll probably discover more of them in the future. I advise you to explore what works for you, explore other approaches, and stick to what works for you.

In a startup leadership role, you’ll be dealing with many situations that will try to bring your and your team’s morale down. IS is only one of many. Being comfortable with hearing “No” and improving your critical analytical thinking could also be a contributors to helping you become bolder at pitching solid arguments, business cases, and solutions without worrying about rejection or being bruised by hearing a “no.” I learned this early in my career while doing B2B sales and business development. I also became better at it when I was fundraising for my startups. As you get higher in seniority within your startup or scale-up, the more amplified the feeling of fraud becomes. It will consume you if you allow it to take over, making you feel stressed and anxious.

Please share your story with me. What worked and didn’t work for you? Your story might be helpful for others as well.

You can learn more about the SAUS Principles through www.skillupasyouscaleup.com.