Did Dating Just Get Harder? Life as an Entrepreneur

Did dating just get harder? Life as an Entrepreneur

Today marks 18 months of being single and if I’m honest, I’ve been avoiding the whole subject.

Yep that big word beginning with D has been on my list of topics I’ve been avoiding.


Did dating just get harder? Life as an Entrepreneur

Well ok, maybe I haven’t quite avoided it.  I did sign up to Match.com about 8 months ago.

However, after a couple of days of cringing at the fact I now live in a small town, where I grew up, and already know the first 20 people to pop up as matches, I then did zero with it.

I did so little with it, that when my 6-month membership automatically rolled over and they charged me for another 6 months, it really was down to the fact I’d completely forgotten about it rather than choice. Don’t you just love that thing called unroll.me which helps you avoid certain emails by grouping them all up in one handy (deletable) email each day!?!?

I could play the ‘I needed time’ card post separating with Karl but the reality was that I’d been distancing myself emotionally for some time pre our split. Yeah, of course, it involved a decision where I ended up selling my home and I threw in a job move all at the same time, so there was some emotion involved. But quitting my job and moving back to Scotland all helped distract me. Why start dating in one county, when you are already planning to move 500 miles away. It was a good enough reason to avoid it!

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But when that match.com subscription alert pinged informing me that my membership had renewed, I realised that dating just got a lot harder.

Yep, I’m 38, not 21 and spending my Thursday nights at Walkabout in Angel. I now live in very small town in Scotland and not in busy London where it felt easier to get out and meet new people. I now work on my own and don’t have the benefit of those work do’s or that quick drink after work where you might bump into someone new.

Yep, I had all those issues to get over to meet someone and then I go and make it harder by popping Entrepreneur onto my CV.


Dating an Entrepreneur

Entrepreneurship has so many amazing benefits including the ability to work when and how I want to. With the right effort and a lot of hard work, I can create a business that works for me.

But the reality is, particularly doing any start-up or expansion that it can also mean craziness and uncertainty.

While my previous job was far from a standard 9-5 work routine, as a business owner I need to wear all hats.  The beach huts themselves are open 7 days a week, so I have to be ‘on-call’ too. My current working life doesn’t quite compare to working in a more ‘stable’ role and I suspect it doesn’t really go hand in hand for many seeking someone to ‘settle’ down!

Entrepreneurship isn’t for everyone and there are many who won’t understand why I’ve chosen to do this now. So, who on earth at my age would be willing to put up with that lifestyle from someone who has?!?!

Oh and let’s not forget that it involves living a large part of my life in the public eye. Yeah, these blogs, those videos and vlogs. Well, not everyone will be comfortable with that aspect of work either and as you know, I can be known to just get my thoughts out there. Sometimes they are controversial ones too!

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OMG! One search on google and they can actually watch and read all this stuff before they actually meet me now too. Eeeeeek.


The Real Issue

But let’s cut to the chase.  Is it really the fact that I’m an Entrepreneur that has made me avoid dating?  Err, no and I’ll take a big deep breath before I’m really honest with you:

I’d have to actually put myself out there to find out.

I’d have to make an effort.

I’d have to actually speak to people who are single.

I’d maybe have to take match.com off my unroll.me roundup.

I’d have to respond to messages.

That’s the real issue.

Yep, all my points about entrepreneurs being difficult to date and a ‘turn-off’ could be true but it could be a big pile of dog poo too!

The irony is that I can be braver.  I can decide to learn how to ride a Harley Davidson motorbike and own one. I can decide to head off to Malawi on a female entrepreneur expedition. I can even start two new businesses in a year. I receive so many amazing comments about my adventures but when it comes to relationships, for some reason I haven’t quite been so fearless.

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Being Fearless and Vulnerable

So this week I did it. I responded to an email. I even responded to the question “so what is it that you do?”.

They answered back.  So one barrier down. Phew.

I may even have agreed to a coffee.

I’ve a long way to go to be just as fearless when it comes to dating as I seem to be with other aspects of my life.

Well come on. I’m 38. I’m an adult.

Surely I can be brave enough to do this. Can’t I!?!?!??


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