‘Only losers don’t feel like losers’ – DVF.

I was reading the Diane Von Furstenberg piece in The New Yorker today. The interview is a perfect example of how showing vulnerability can paradoxically make you look even more strong than if you hadn’t shared weakness at all. At one point she said:

‘I’m true to myself. I mean, sometimes I feel insecure. Sometimes I feel like a fucking loser, and I say, “I’m a loser!” But only losers don’t feel like losers.’


That part of the interview really struck me. It speaks to how human it is to experience self-doubt, insecurity and a fear of failure, even if you are DVF. It also shows how, just by taking a broader perspective (thinking outside of ourselves), we can quickly mitigate the moment of weakness and restrengthen ourselves on the purposeful path forward.

Entrepreneurs often feel the pressure to show no vulnerability, to ‘fake it till you make it’, to believe in themselves 100%. And yes, while these principles can have their place, it is wrong to ignore or minimise the fear of failure that the majority of entrepreneurs experience. Having a fear of failure is normal, especially when we are walking down a path that no one has been down before and we are doing it primarily alone – that is, the responsibility for success (and failure) falls squarely on our shoulders.

Experiencing a fear of failure is a part of the entrepreneur’s journey. It can’t be ignored or gaslighted, it needs to be acknowledged and dealt with honestly. From my observations and experiences, it’s smart to shine a light on the monster under the bed, reconnect with our ‘why’, say no to isolation, and become a broken record in reframing the experience of failure. See below for more details.

1. The Monster Under The Bed

The more you come face to face with the monsters under the bed the less they seem like monsters. Get to know all your fears at different scales. What are your fears in reality? And what are the chances of them happening? They could be as big as bankruptcy or as small as not knowing the answer to a question posed by colleague. It could be that the fear is exaggerated and the chance of it become a reality is so slim. Or, it could be that there’s a 50-50 chance that your fear comes true.

Regardless of the possibility, play out what would happen if your fears came true. What is the experience like? Is it something you think you can work through? In order to work through it, are there specific things you need to practice and thought patterns you need to avoid?

For example, what if you have a conference coming up and you are fearful that you will walk into one of the network events and have no one to talk to. When you imagine experiencing this, what is it like? When you imagine working through it, what do you do? What might you need to practice or reframe for yourself so that it simply becomes a human experience not an act of failure? You may feel like a loser temporarily, but then again, only losers don’t feel like losers.

2. What’s The Point?

Reconnecting with the ‘why’ – the purpose behind your hard work – instrumentally helps you to persevere when you are facing fear head on. What drives you to keep showing up even when it is scary? Why not just turn around and go back to bed or to that secure 9-5?

When you connect with your ultimate vision try and visualise it. Really imagine what it is that you are working towards and see your values come to life in your minds eye. Revisit this scene as often as you need to. What you believe becomes your reality, even if there are bumps along the road to get there. At the end of the day, if we can continuously remind ourselves that the risk of failure is worth it then… it’s worth it. Focus on building your perseverance.

3. Say No To Isolation

Fear of failure is always driven by deeper beliefs like ‘failure is shameful’ or ‘failure means I’m not worthy’. Doing the work to understand and see these limiting beliefs clearly will help you to change them into empowering beliefs like ‘failure is par for the course’ or ‘failure is just an opportunity to learn’. But it can be hard to shift perspectives and change beliefs and many entrepreneurs feel ill-equipped to do this alone.

I often talk about the concept of smart vulnerability with my clients – the idea that you know who you can be vulnerable with and to what degree. Many leaders feel there aren’t many people around them that they can be vulnerable with and this blocks them from facing up to and managing their fears. Often other founders, leaders and entrepreneurs can provide that kind of support and accountability as well as trusted family, friends and professionals. When you learn to be vulnerable in these safe relationships it becomes easier to reframe a fear of failure within the context of the wider world.

4. Be A Broken Record

Weeds are persistent and resistant. Even when you think you’ve successfully eliminated them from your garden they reappear with a vengeance. You have to keep weeding until they are gone for good. That is, repetitive action is crucial and repetitive immediate action is even better when it comes to managing your fear of failure.

Every time you sense a fear surfacing whether it’s through a total hijacking, an emotion (think anxiety, nervousness, irritation, shame) or a self sabotaging behaviour (like avoidance, hyper-achieving, hyper-controlling, perfectionism) take a step back and assess:

  1. What am I actually afraid of?
  2. What is the chance of it happening?
  3. Is what I’m attempting to achieve worth this potential failure?
  4. Who can help me work through this on a deeper level be it a friend, colleague or professional?
  5. And ultimately, how can I keep reframing failure as a normal part of entrepreneurship even in the most high-stakes circumstances?

Practice makes mastery.