Three years ago I left a good position in a well established company to follow an ambitious dream. At the time I formulated it something like this: “I will open minds and hearts to help create new possibilities and hope. I will facilitate the discovery of a better future – one where we are connected in more authentic ways”. I remember how good, but also how scary, it felt to claim that vision for myself. I had a strong sense of what I was supposed to do and I felt ready to step into it but I had very little idea on how it was going to unfold. Three years later there are still many unknowns but there are also many valuable insights I have gained along the way. I am sure they will resonate with many fellow entrepreneurs and I suspect (hope) they are also increasingly relevant to more established organizations.


Lesson #1: The initial goals, strategies & measures you set for yourself won’t last.
I will always remember the day I announced my intention to leave. I was making a clear choice to go after a dream, and was full of hope for the future. This energy carried over into the first couple of weeks & months. Everything was fresh and exciting, everything was possible. I created an ambitious plan for the next three years and clearly defined my USP, target market, financial goals, marketing strategy etc…I ticked all the boxes. As I moved to implementation mode however, things started to get off track. I wasn’t signing as many clients as I needed to meet my financial target and my message wasn’t coming across as clearly as it had been in my head at the onset. When people asked me how things were going I noticed that my story was considerably less upbeat than 6 months earlier. What had happened? Were my hopes and dreams being crushed already?


Lesson #2: The essence of your vision is the only constant you can rely on.
My default reaction was to take a step back into my comfort zone and broaden the scope of my work to also include more mainstream consulting projects. It seemed like a reasonable thing to do but after a number of such projects I started to feel the same restlessness as before. I knew that the vision I had committed to would not go away, I knew it would keep tugging at my heart. What needed to change was not the underlying purpose of my work but the mindset and approach for bringing it to life. This encouraged me to re-define my strategies, goals and measures in a way that reflect the long term aspect of this work and encourages me to put more focus on the elements that are in my control (such as building credibility and trust, sharing ideas, starting a dialogue…).


Lesson #3: Choosing to leave a stable job in pursuit of an entrepreneurial dream is a big commitment and takes courage but it is nothing compared to the commitment and courage needed to keep the vision alive on a day to day basis.
In re-committing to the original vision I was making a choice to be true to myself, to stand up for what I believed in and what I can uniquely contribute. In saying “Yes” to my dream I was saying “No” to many other potential avenues but I was also creating the space for more aligned opportunities to present themselves. From then on I realized that commitment is not something that you do once or twice at some critical milestone. Instead it is a continual, day by day, moment by moment, process of re-connecting with the core of what drives us and choosing to meet the world from this place.


Lesson #4: It helps to stay committed when other people believe in you but don’t seek it out as a substitute for believing in yourself.
In the beginning, I personally found it very important that my close friends and family trusted me and believed in what I was doing. In some ways I thought of it as a validation, and my confidence depended on it. This of course was a dangerous trap. The love and respect between friends and family will always be there, but truly getting people on board with my project is something I would have to earn. Realizing that my desire for external reinforcement / support was in fact driven by a lack of belief in myself was a huge eye opener. To continue on this journey I knew I had to re-calibrate my definition of success and create an environment where my own self worth did not depend on the outside world.


Lesson #5: Success is not found in what you do & what you’ve achieved but who you’ve become in the process.
To move forward I had to let go of my attachment to outcomes. I now pay much more attention to how I am feeling in the process. For example, am I inspired? Or am I responding to challenges with an open mind & heart? I know I am on the right path when the honest answer is “Yes”. In these moments I just continue to stay in the flow. When the answer is “No”, however, I try to take a step back and broaden my perspective on the situation. Feeling stuck can be painful and the temptation is to just “get on with it”. The real opportunity though comes when we stay with the tension and open ourselves up to the opportunity that lies beneath it. This will not always be easy to recognize and often it requires us to stretch our thinking, challenge our assumptions and take action in ways that may feel uncomfortable. However, it is when we stretch ourselves in this way that we can truly grow as individuals and unlock the necessary breakthroughs for our project.


Lesson #6: The bigger the dream, the bigger the challenge to engage people in a compelling way. Or in other words, the bigger the dream, the more rejections we will have to deal with.
A big part of my job is taking new ideas and concepts and making them more tangible / accessible to the mainstream world. In many ways it is a trial and error process where the ultimate goal is to create that spark of connection, the aha that opens a new door and gives a glimpse of what could be. It’s impossible to get this right from the beginning so inevitably responses will range from “so what”, if we meet them in their comfort zone, to “silence” or “blank look” if we meet them too far out. It is only when we pay close attention to the responses we get and manage to transform them into a rich source of inspiration that we will eventually start getting close to that magical sweet spot where people trust you to take them on the journey. Embracing this challenge as a fundamental part of what I do has made this work so much more enjoyable.


Lesson #7: Financial independence & comfort is a critical measure of success but be careful what you benchmark against. What you think you need to be successful, may be based on some outdated assumptions & no longer hold true.
I used to think that after the first three years I would be earning more or less the same as I had before. I somehow believed that this was the amount I needed to enjoy a comfortable life. Along the way though, as the numbers were not adding up, I realized that what I needed to be happy turned out be very different than what I originally thought. My attachment to material objects seemed to have decreased in the same way as my attachment to business results and eventually I was living a simpler, more balanced & fulfilling life. As my work matures, and I find that spark of connection with more people, I am sure that my financial needs will continue to be met.


No matter if you are an entrepreneur or you work for a more established organization, I hope that these lessons resonate in some way. In any case, I wish you much success and, perhaps more importantly, lots of fun along the way!