Skip to content

The Toughest Moment in an Entrepreneur’s Life

And how to overcome it.

Suspension bridge across the forest

What is the toughest moment in the life of an entrepreneur? Young professionals and founders ask me this question quite often. Be it during a guest lecture, a presentation, or in a personal conversation — the idea seems to occupy aspiring entrepreneurs.

Of course, this question cannot be answered simply in general. Every person is unique and therefore perceives a very individual situation as THE “hardest moment”.

That’s why I first ask those seeking advice a simple counter-question: What do you think is the hardest moment in the life of an entrepreneur?

In eight out of ten cases, the first impulse answer to this question is the failure of one’s own company. But is that actually the case?

In my humble opinion, a resounding NO. Especially if you look at the topic from an international perspective. The “culture of failure” in the USA, for example, is completely different compared to Germany, India, or Singapore.

Because of this diversity, I would like to answer the question based on my personal experience and countless conversations with experienced entrepreneurs and executives in an international context.

So let’s dive a little deeper into the topic together.

The toughest moment in the life of an entrepreneur is not the failure of your own company, but when you lose self-confidence.

When I share this thought with my interlocutors, I experience very different reactions: from astonishment to pausing to disappointment, everything is there.

I find the latter reaction particularly valuable. Why?

Not infrequently, this disappointment is based on the fact that self-confidence is taken for granted by entrepreneurs. And, to make it short, it is.

If my conversation partner and I get to the bottom of the aspect of self-confidence in the course of our dialogue, one thing also becomes clear: young entrepreneurs in particular often only have a vague idea of the concrete consequences of the loss of self-confidence that is so taken for granted.

It is precisely at this point that there is a great opportunity to develop further as an entrepreneur and also to grow as a person.

Why self-confidence is so important for entrepreneurs

In many cases, you don’t realize how important self-confidence really is in the life of an entrepreneur until you’ve already lost it. Suddenly you are faced with completely new challenges. On the one hand concerning your own company. On the other hand, as far as yourself is concerned.

The descriptions in our conversations are as personal as the entrepreneurial personalities are diverse. When I think back to my personal experiences, I remember the following story in particular:

It was at a time when I was unsatisfied with my entrepreneurial direction. Up to that point I had achieved a lot in the previous years. However, the outlook for the future did not offer what I would like to do from an entrepreneurial point of view and also personally. A course correction was therefore necessary.

Knowing that this would not be an easy path, I spoke to my family beforehand. My experience over the past decades has shown how important this support is for an entrepreneur.

I was all the more grateful when I received the trust.

The rest of the story is easy to explain:

As every successful entrepreneur knows, a company is always associated with opportunities and risks. Especially in the first few months and years, this can mean a high degree of uncertainty for everyone involved — an uncertainty that not everyone is willing to bear to the end.

One of those participants on my way was my then-wife. Despite an intensive discussion beforehand and her consent to the course correction, it became clear to her that this was not the path she wanted to go on in life. I don’t want to pass judgment on her decision. Neither does the way she embarked on her new path in life.

The marriage fell apart. Nothing in itself unusual in this day and age, and especially nothing to throw an entrepreneur with strong self-confidence off balance.

Nonetheless, the impact has been huge, both from a business and personal perspective. Since there was not a single conversation leading up to this decision, the situation hit me out of nowhere.

I suddenly felt like I couldn’t trust my instincts anymore and went into a downward spiral. I wasn’t aware of this at all at the time. However, I quickly began to notice the negative effects this had.

I now know that my confusion was interpreted as a lack of self-confidence. This unsettled many people around me, such as the teams I worked with on international projects. Or business partners who saw my lack of determination as a weakness and subsequently turned away.

It was an essential experience that the loss of one’s own self-confidence interacts with the loss of trust in those around us.

So never wait for others to have your back. Should it nevertheless surprisingly be the case, it is all the more valuable.

As an entrepreneur, I have learned three important things for business and life:

  • 80% of people don’t care about your challenge and 20% are even happy that you’re in this problem situation — and if you’re lucky, there are a handful of people who stand by you
  • Never give up, no matter how hard life gets
  • Money is replaceable, self-confidence is priceless

How entrepreneurs can boost their self-confidence

There are certainly many ways for entrepreneurs to boost their self-confidence. To be honest, I’m not a fan of talking to myself in the mirror or making clever quotes like “always think positive”.

Anyone who has experienced what a loss of self-confidence can do is well aware of one thing:

Positive thinking alone cannot bring about real change. Only the action we actually do leads us to a new result.

Over the years I have tried many things and appreciated a few solutions. In the following I would like to share four of them with you:

1. Make a clean sweep

Mucking out and tidying up are two essential cornerstones when it comes to creating clarity. This applies both to entrepreneurial goals and to business and private relationships. My experience is that far too often you make compromises with yourself and ultimately decide against yourself. When it comes to eating, on the other hand, it’s easier for us: we don’t eat what we don’t like. So why not make decisions just as consistently from an entrepreneurial point of view?!

2. Set clear goals

The be-all and end-all in life are clear goals. In conversations with young entrepreneurs, however, I keep finding two points: either the entrepreneurial goals are very vaguely defined or too many goals are being aimed at at the same time. Both lead to success in the rarest of cases. The focus on the essentials, or in business terms on the maximum added value, is a critical success factor.

3. Think and act in solutions

Building a successful business involves one thing above all else: challenges. These accompany us as entrepreneurs every day and it is our task to solve these challenges. I experience it again and again that numerous entrepreneurs recognize their challenges, but then stagnate in the description of the problem and the search for the cause. In this situation, it is much more important to develop possible solution scenarios for a specific challenge and then to implement the most promising of them.

4. Always trust yourself first

I am aware that this point divides opinions. However, I don’t believe in seeing things in life exclusively in rosy colors and therefore not addressing sensitive topics. As an entrepreneur, you cannot afford this luxury. Incidentally, point no. 4 does not automatically mean that you cannot trust your employees, business partners, or other stakeholders. But on the contrary:

I believe that you have to trust yourself first of all to trust other people.

Final thought

To revisit the opening question, what is the toughest moment in the life of an entrepreneur?

A partial aspect of the answer remains the same even after writing/reading this article: every person is unique and therefore perceives a very individual situation as THE “hardest moment”.

Nevertheless, I firmly believe that our self-confidence plays a central role in overcoming challenges. The mental handling of problems determines our actions.

The subsequent decisions cannot be taken away from any entrepreneur, because it is in our nature to make decisions in every situation.

Mike Flache
Mike Flache

P.S. My posts focus on digital growth. From time to time, I also share my experiences on topics such as leadership, entrepreneurship, and personal development. If you’d like to receive my articles by email, you can subscribe here.

Cover image: Jonathan Klok on Unsplash

Disclaimer: The information provided in this post is solely the author’s opinion and not investment advice — it is provided for educational purposes only. By using this, you agree that the information does not constitute any investment or financial instructions. Do conduct your own research and reach out to financial advisors before making any investment decisions.

Enabling digital growth

Leverage Tomorrow's Business Opportunities Today

A global perspective on digital business trends and innovation. Thursdays by email, no spam.

By submitting the information above, we will send you emails from Mike Flache with insights and perspectives on digital growth. You can always opt-out by clicking on the unsubscribe link within those emails. By clicking “Sign up – it's free” you agree to our privacy policy.