Risk: what do you stand to gain from risking it all?

My family often think I’m crazy. Who in their right mind starts over at the age of 34 with 2 small children? Having worked hard on my previous business to build it up and get a ‘good wage’, shouldn’t I have continued? Or at least got another ‘good job’? I am used to their looks of concern, when their eyes get crinkly, their lips purse slightly and their arms cross (we are English after all, it’s all in the body language). Even my father, who has spent his whole life risking his future and his present on business ideas, talks to me in cautious tones (I’ve notice this with other entrepreneurs actually, like actors they are not always thrilled when their kids follow their path).  My family are incredibly supportive and have done everything to help – it’s more that for me it raises an interesting question about risk – what do you stand to gain from risking it all?

I spent my 20’s admiring my friends who were climbing the ladder and earning good money. I would envy their ability to be sensible and yearned for a time when I would magically wake up and make life choices not on how exciting my ideas were or how much potential they had, but on how much money I could earn from a regular wage. I felt out of kilter with my friends and I wondered if I was just someone who was really irresponsible.

Now in my 30’s I look around at my friends and see many of them in jobs in which they feel trapped. They’ve taken on big mortgages or have high spending lifestyles and so don’t feel they can leave their job and pursue their real dreams because they have become reliant on the pay check. I think its fine to be in this position if that is what you want. Of course people have to provide for themselves and their families. I don’t think society would work if we all went out and started businesses. It just seems very sad if people want to do something else but feel they can’t because the risk is too high. It’s not just about starting businesses but creating a life that you really want to live in.

It’s hard to step off the land of security; even I experienced severe doubt when I handed in my resignation. I had built a company up, grafted through the hard start up years and was earning a good regular wage. The idea of starting all of that again was scary, but I knew that not doing it now was more of a risk that carrying on.

My favourite friend’s grandmother Sonny once told me a story about her life which I found incredibly inspiring and filled me with awe for this amazing woman. Sonny’s family left Poland in the 1920’s and arrived in the States when she was little. She married, had three kids but her husband died young. She then married a salesman. They were not well off people. One night her husband’s bosses came to dinner, drank too much and revealed that they wanted to sell their company. Her ears pricked up. The next day she pursued it. They borrowed as much as they could, mortgaged themselves to the hilt and bought the company – even though they didn’t have money for the first month’s payroll. Everyone, including some of her kids, said she was crazy. Her response was – well it would have been more of a risk NOT to do it. How else did I stand a chance of paying for my kids’ college fees?

Over the ten years they had the business they worked incredibly hard, dealt with all the up’s and down’s inherent with running any business and made good money. They were able to pay college fees for both her children and grandchildren (and this is America we’re talking about, it’s not cheap) and so her risk paid off. And for me this is the key to looking at risk – most people just look at what they would be giving up when they think about doing something new like starting a business , but they don’t look at what they stand to gain. If you are not getting what you want out of your life now (be it more money in the bank, more time with your kids, more enjoyable work, the opportunity to travel to far flung places etc.) then how do you think that by carrying on and doing the same thing over and over you’ll get to that place? It is necessary sometimes to stop, examine and take a huge ass leap with the desire that you’ll get more of what you want from life. Of course it’s hard – but then what isn’t in your post 30 life? No one I know has what I would call an easy life.

Photo by Anthony Epes (the husband) from his series Arboreal Dreams.




7 thoughts on “Risk: what do you stand to gain from risking it all?

  1. Well said Di! And if it feels a bit like vertigo in your thirties to take that leap, imagine what it’s like at 50. I am enjoying that freefall feeling tho’. Don’t lose your nerve – P x

    • Thanks Penny! I am regularly loosing my nerve but managing to get it back pretty quickly 🙂 I hope you are doing really well – what are you plans? So exciting to be doing something new!

  2. I have to say: this post is VERY inspiring to me. At the ripe old age of 38, I find risk- taking tougher than ever. You’ve reminded me that it can, and often should, be done. Then again, the way you live your life has always reminded me of that.

    It does make me think of one of my favorite cards ever, which has a black and white photograph of a teenaged girl dressed up in what looks like her marching band finest, with a hat, and a white skirt, and an umbrella, and she’s jumping over a giant mud puddle in a field. Underneath, it says: “Ever notice ‘what the hell’ is always the right decision?”

    P.S. My grandma was so surprised and honored that she had inspired you. Thanks for thinking of her.

    • Thank you Lady Cara. I love that! That girl is totally right. I am really happy that your grandma was pleased – she is one of the most inspiring people I’ve ever met. I could listen to her for hours.
      P.S. One day I will learn how to work on the internet in real-time and do things like reply to comments in a less tardy fashion. I might even learn to spell too 🙂 Eek.

  3. I remember these days… two children & a mortgage to support, all through my freelance efforts. Today I am looking at a whole new future as my youngest leaves school & all sorts of plans [mine & his] are to be made. Life is a constantly evolving and reinventing process & all I can tell you from the other end of the telescope is that this time of juggling babies & work & life is hard but rewarding & the opportunities you create now will be built on & built on & built on… I thought the world was my oyster when I was 18 but discovered that you never eat a single oyster, they always come in quantities of six! Treasure & enjoy, it goes so FAST!

    • Thanks so much Harriet. I love the idea that oysters come in sixes! What a great concept and I think very very apt. It’s so true that life is constantly evolving and I think once you embrace that it makes the change feel so much more natural – like the great adventure that it is. I can’t imagine my little ones leaving home, but I know they will. One thing though that will be great about that is seeing the adults they become. I already love the conversations I have with Theo, his take on the world fascinates me and he is only 6! I just hope I give them everything they need to flourish, not just now but as grown ups out there in the world. Good luck with your new plans and adventures.

  4. I loved what you did with the Wedge Card and sorry to see the site sitting dormant. Nevertheless I am impressed that you did not get too comfortable and are pressing on to new challenges. I am 10 years ahead of you on life’s path and recently set off on a start up which has me both energized and exhausted. It is still at a very early stage, but would love to get the opinion of someone that has been down a similar road.

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