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Why is optimism important when you start a business or freelance career

Since the beginning of 2024, I’ve had the opportunity to work with people who want to shift from a 9-to-5 job to a freelance career or from a freelance career to a solopreneurship or entrepreneurship path. And it’s been amazing to see how much optimism matters when you start a business or freelance career.

I’ve been a freelancer since 2012 and had my trials and errors with entrepreneurship. Soon I might give it another shot. But it feels like after COVID-19, many more people want to make the shift and … it’s chaos.

People struggle with understanding what they’re embarking on, the resources needed, how to balance the transition, and discover the new skills that they have to learn as a freelancer and business owner.

But is more than that.

All these years in which I’ve explored what personal development is, I understood one simple but valuable thing: what you want to improve at first is not what should be improved so you can overcome your challenges.

For example, a few weeks ago, I had a coaching session in which the coachee said they wanted to have their travel agency and shift from a freelancer role (where you work for a travel agency) to owning the business.

Quite rapidly, that session changed the topic from ‘how do I make the shift’ to ‘I struggle when I have to ask for money for my services’ and advanced into ‘the adult that I am today seems to want to protect the psychological child that I still carry with me and that is strongly related to me asking for money for my services’.

It’s insane how deep can a situation go when you’re willing to explore what’s going on with you when you decide to play a new role – to explore how you feel and what triggers these feelings.

Optimism is the sailing ship you need in an ocean full of challenges that could sink you

Imagine you are making the transition to freelancing or entrepreneurship, and when you do that, you realize that you don’t know how to sell your services.

You are amazing at what you’re doing and you’ve always had great results. Your manager was always happy to have you in their projects and you’ve been a valuable colleague to your teammates.

While being an employee you don’t need to have any sales skills, these skills are required for the role of a freelancer or entrepreneur. You NEED to be able to sell your services and/or products because making money is an important part of having a healthy business.

If you don’t believe you can improve, then you won’t.

Even more, this is one of the few responsibilities you can’t delegate.

When you want to start a business, you can delegate accountability, customer support, branding, and many other aspects of your business. But you can’t delegate the beliefs you have to have about your business so you can succeed.

You must be the one who believes that your business will thrive and overcome all the obstacles. Nobody will do that for you.

The same goes for running a marathon. You can delegate the development of the running schedule and have someone pick for you the running shoes. But you can’t delegate the belief that you’ll successfully run 42 kilometers (26 miles). Nobody will do that for you.

This simple concept applies in every single situation that requires you to have a vision, that requires you to believe it will work out, against all odds.

Short story about Camino de Santiago, optimism, and your inner world

After finishing my first Camino de Santiago, in 2022, a lot of people were inspired by my story. I had no equipment, no plan, and didn’t know what would mean to walk the Camino de Santiago. But I finished it in 11 days, from Porto (Portugal) to Santiago de Compostela (Spain), after walking more than 300 kilometers.

I remember that back then I used to have a friend who was inspired by my journey and wanted to do the same.

I encouraged him over and over again to do it but he kept making excuses. I was sharing with him everything he needed to know so he could feel safe about doing something new, but still didn’t do it.

When you look at it from the outside world, walking the Camino de Santiago is so compelling. You get to hike for two weeks, live like a pilgrim, see a big part of Portugal and Spain, and all this for a small amount of money.

If you live in Europe, the plane ticket is less than 150 euros (to fly from wherever you live to Porto and then from Santiago de Compostela back home). And on top of that, you only pay around 30 euros/day for food and accommodation. In two weeks, the total cost is around 600 euros. That’s cheap. Really CHEAP. And it’s what makes it so compelling.

But when you look at it from the inner world, walking the Camino de Santiago (or whatever you want to do – starting a business or becoming a freelancer) will be just another thing that you dream about doing. But you keep postponing until someone will maybe do it for you.

Nobody will do it for you.

Nobody will ever believe what you are supposed to believe – to believe that you can do whatever you want to do, whatever obstacles and challenges you may face.

Dare to dream big!

The responsibility to believe in your vision is your main job and it’s where it all starts.

Whatever you decide to do today, there will be moments when the odds will be against you but it’s those times that the intensity of your belief in your vision matters the most. After all, when something is important enough, you do it even if the odds are not in your favor.

Create the highest, grandest vision possible for your life, because you become what you believe. Hug every challenge that comes your way because they are essential for your growth. And accept that those around you may not understand you from time to time.

Which is ok. It’s normal. After all, it’s your vision, not theirs.

It’s a risk you’ll have to take. But it’s not the biggest risk because the biggest risk is not taking any risk at all. Risk and learn from your mistakes.

With love and optimism,
David

PS: A similar version of this text was sent one month ago to those who have subscribed to The Optimistic Tuesday Newsletter. Join now and I’ll send you an email every Tuesday, with valuable insights about optimism, just like in this article.

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