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The wonderfully messy life of an entrepreneur

By 19th June 2019 July 10th, 2019 No Comments
The wonderfully messy life of an entrepreneur | All Sorts of Stories

I have a question, how many of you are dreaming one day to leave your 9 to 5 job and do something for yourself?

If you are one of them, this blog might enlighten you and give you an insight to the wonderfully messy life of an entrepreneur and what my experience has taught me.

As half pragmatist I like to always start from the ‘ugly’ so I know where I’m standing.

Entrepreneurial life is not easy and it’s uncomfortably messy most of the times. Prepare yourself, there will be tears (lots of tears) and sleepless nights and various blocks along the way that you will need to overcome to get to where you want to go and you will often lose sight of the end goal while trying to figure out the here and now. Finally the ‘what’s the point of it all’ will cross your mind so many times that you will be very tempted to just give up.

Believe it or not, my aim is not to dishearten you and tell you to forget about it and keep your 9 to 5, instead, to be honest so you are prepared. Aside all the difficulties you might face, the ultimate joy you get at the end of the road, the self growth you gain, the sense of real achievement, is beyond every little tear and all the sleepless nights you might have gone through.

The Jack of all trades

When you are getting lost in your own thoughts of a new idea, something you would really like to do or something different that hasn’t formed completely in your thoughts.  I bet you don’t think that you need to leave your own job and take on another 6 or 7 job titles all at once?

When you are building your own business, you need to be the sole trader of whatever you do, whether it’s service or product based. Alongside this, you might need to be a branding expert, a website developer, a web designer, a marketer, a writer, an accountant, a content strategist, a social media expert, a blogger, an administrator, a photographer and so on! I tell you something guys IT IS exhausting! Unless you have a big pot of money that you are happy to invest on all of those, then you need to find a way to make things work and I’m telling you from my own experience, the struggle is real!

What do I know?

I’m not new to the entrepreneurial life. This is my 5th time that I’m starting something from scratch.

My 1st experience was more than 20 years ago and it was a complete ‘car crash’. A new start-up with my brother we built a fantastic product, but it was way ahead of it’s time and in a market that wasn’t ready for it and with no real marketing or sales plan in place, so inevitably 9 months later, broke and broken we all went back to our 9 to 5 jobs.

My 2nd attempt was again with my brother, his idea of starting a cycling blog was born from my one bedroom flat in Greece, 4 years later his business hit his first million turnover and had 12,000 active cycling members – a real active community and that was before social media existed. This humble blog was transformed to a very successful e-store and forum, two massive retail stores and a cycling club. I was there from the start and was leading the branding and design side of things for the retail and the online store but also all the marketing campaigns for the club activities. Was it easy? Hell no! But the rewards, the sense of achievement and the know-how I learned, working by his side and the experience I gained from what it became a hugely successful business, was second to none.

My 3rd go was when I joined a new start-up of a very good friend of mine, Shelly Hoppe. “Southerly”, a content marketing agency, was born early 2009, that was before even content marketing was even a thing. My role was to lead the agency’s brand evolution and to build a strong brand, through all channels of communication and boy, what a ride that was! We started with just a handful of people working remotely, mainly Skyping each-other. I remember launching the first company’s website on Christmas Eve, working insane hours to make it all happen and we did!

Southerly became one of the top boutique marketing agency’s in London. I stayed with the agency for 9 years were I had the opportunity to recruit many highly talented designers and lead Southerly’s studio while venturing the corporate world through our very high profile clients. Southerly has now been acquired by a Swedish Global agency called Spoon and it’s sailing onto new horizons on a brand new shiny boat! WHAT A JOURNEY! So many successes, so many tears, so much growth, so many learnings, it’s just insane to think back.

My 4th attempt was to start my own Interior design business, and that didn’t go as well as I thought it would, but I have written a blog about why it didn’t work here.

And that rollercoaster now brings me to my 5th beginning. Starting again from scratch a new business idea but with all the great experience I’ve gained over the past 20 years. A more intentional approach to everything I’ve learned, to everything I have experienced, and I have to admit I feel more grounded and more at home than ever.

The wonderfully messy life of an entrepreneur | All Sorts of Stories

You can do this!

I will tell you a secret, there are ways to make the tough bits more manageable:

  • Forget the 5 steps to success strategy. It’s all fake news! There are not 5 steps to do anything when it comes to building a new business. You need to be consistent and patient. No business has become successful over night. It needs hard work, dedication and determination and you need to be comfortable with being uncomfortable. Once you know and fully understand this, you are already winning. Can you do this?
  • Everything takes time! Don’t try to rush things, plan your time wisely and give yourself and your business time to grow. Investing time while you’re building your foundation will only help you grow stronger and more sustainably. Don’t try to join the fast lane too soon, you will only burn out.
  • Clarity. Never start something before you have clarity on your vision. Why are you doing what you’re doing? What is your end goal? What you are trying to achieve? Work on these and find your clarity and focus before you even start.
  • Strategy. Things change all the time, and you need to be flexible, especially in the beginning. But have a plan! Even if that plan changes, take time to think things through before you even start. Every little thing you might need along the way, plan it out!
  • Never, EVER compare your start with someone else’s middle or peak. Most of the time you have no idea how much work and what others had to go through to get where they are on their journeys and how much they have invested. Also there is a trend the last few years, especially with bloggers and Instagramers to present themselves as casually doing what they do by themselves. But what they don’t tell you is that most of them have teams working behind the scenes and a lot of money invested on them. No perfect image or strong brand was casually made by one person! Trust me on that!
  • DON’T be a Jack of all Trades! You want to do everything by yourself and you think you are a good multi-tasker? Think again. You won’t have enough time! You will end up pushing yourself to the limits and crash. Focus on the things you are really good at and where your passion lies and work on that. Find your people, your support, there are ways to find people that can help you even on a small budget. Have you thought about skill swapping? That worked for me many times. It’s a win-win situation. Find a way and leave the things you can’t do to the experts!
  • Connect. Spend 70% of your time building the thing, and 30% of your time making real connections. Meet with people that you think can help you move forward and have conversations with them, exchange ideas, talk through your challenges. You will gain SO much by doing this. You don’t have to be alone and try to figure everything out by yourself!
  • Finance. Have a clear understanding of how much work is involved for everything you need to do and put a price on it. Do you have the money to do this? Or can you find the money to do it? Be clear about your finances before you start.
  • Find your emotional support. Now this is a big one. There will be tears, trust me there will. Who is the person that can listen to you when you are navigating through this messy entrepreneurial life? Is it your partner, your mum, your best mate, your neighbour? Emotional support is not something you think you need when you start a new business, but you know what, we are only humans and we need a release. Don’t go to the battle all alone! Emotional support most of the time can do wonders, it gives you a different perspective of things and helps you move forward.

I have been fortunate to work on projects that were a huge success but also in projects that ended not in the way I was hoping. I say fortunate because I believe everything happens for a reason, and when something doesn’t work, we need to take away everything we learned, let go and move on.

Not everyone is suited to work on their own but the more clarity you have before you start, the more you can make the process more manageable. I was never comfortable on a 9 to 5 job and that’s why I always started my own projects or joined start-ups. There is something very exhilarating when you building something from the ground up. The immense joy, the tears, the successes and the failures. I wouldn’t change a thing!

Now… is this for you?

Much love to you,


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The wonderfully messy life of an entrepreneur | All Sorts of Stories