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Successful and single? The dating dilemma of high-achieving professionals (and how to overcome it)

How you can - and why you should - apply the same strategies in your love life as you do in other areas of your life.

You have an impressive CV packed full of senior job titles and big-name employers. You worked hard and played hard throughout your twenties. Then, suddenly, you wake up one day and look around you to find that *everyone* has married and popped out at least two children. And, like Hillary Clinton, you ask yourself: “What happened?”

The truth is that you would like to meet someone and maybe start a family. And it’s not like you’ve done that forbidden thing of focusing too much on your career to the neglect of finding a partner. You just weren’t ready before. And you’ve been busy! Yes, with work, but also with friends, with travel, running marathons, having fun.

And now that you’re ready to meet someone, you don’t know what to do about it. You’re used to setting goals and working hard to get what you want in other areas of your life. When it comes to love and relationships, though, you’re not so sure.

But although it may feel a bit odd at first, you really can – and should – apply the same approach to relationships as you do in those other areas.

Full disclosure: In no way do I see myself as a relationship expert and I’m reluctant to offer any kind of advice. But I was this person a few years ago. I didn’t need a man. I didn’t think I could meet the right man. I certainly didn’t make time or space for a man. And a few little tweaks to how I was thinking and what I was doing completely shifted my perspective. The result was, first, a number of amazing connections and, now, a loving relationship. No one knows what the future holds – but I do believe there are some things you can do to stack the odds in your favour.

1. Getting clear on what you want

The biggest barrier to getting what you want in your career is not knowing what that is – and the same applies in love! Do you know what you’re looking for? And I don’t mean “6ft, dark hair, athletic”, that’s neither specific enough nor meaningful. You need to get clear on what (or who) it is you’re looking for if you’re to have any chance of finding it, and of knowing that you’ve found it when you do.

Close your eyes and try to visualise your ideal partner:

· How do they make you feel?

· How do they treat you?

· How do they treat their parents? Nieces and nephews?

· What core values do they have?

· What personality traits are most important to you?

· How do they relate to your career or business goals?

· Do they want children?

· What kind of things do they get up to in their spare time?

· What else is important to you in a partner?

· And, not just your partner: what type of relationship do you want?

Write your answers down on a list. You don’t need to show it to anyone, but looking at it from time to time will help you to remember what’s really important to you and, if you’re open to a bit of ‘woo-woo’, will help you to attract that person into your life.

(I don’t want to be smug but I wrote a list in my notepad a couple of years ago and my partner matches all of them. Well except one, but sometimes there’s a compromise to be made… 😉 )

2. Working out what’s getting in your way

As with anything in life, there are usually all sorts of fears that are getting in the way of meeting, and committing to, a long-term partner. Fear of getting hurt. Fear of wasting time. Fear of making the *wrong* choice.

And that last one especially is a problem. These days, compared to when you lived in a little village and would marry someone local who was from a limited-but-clearly-defined pool of candidates, you have too much choice. Someone doesn’t reply to you on Tinder? Doesn’t matter, you have 27 other matches. Someone doesn’t make you laugh on your first date? No problem, you’ve got another one lined up tomorrow. There are too many fish in the sea! And, on top, your single life is so great that it would require someone pretty damn spectacular to come along and take up space.

If you dig a bit deeper you’ll find a host of underlying beliefs that you have formed either based on personal experience or based on what you’ve seen in your parents, your friends, or even on TV. It’s worth examining those fundamental beliefs and thoughts in order to uncover what might be getting in your way.

A few examples of underlying beliefs:

“I don’t need a partner (but I want one).”

“I don’t want to come across as being needy and desperate.”

“I’d rather be alone than with the wrong person.”

“I’m independent and I want my freedom.”

“I’ve never met someone who ticked all the boxes.”

“All the good ones are taken.”

Can you see how those beliefs might be limiting your chances of meeting someone? (I certainly could when I wrote down pages and pages of thoughts like these a couple of years ago. Who in their right mind would want to date someone who was going around saying they didn’t need to be with anyone?) Try writing down your beliefs and see how you can turn them into more positive ones, beliefs that are just as true and that will serve you better.

Here are some ideas:

“It’s okay to need someone. Opening myself up to relying on another person doesn’t make me weak.”

“Admitting that I’d like to meet someone is natural and an important first step to actually meeting that someone.”

“I’m clear on what I’m looking for in a partner and there’s no reason why I would settle for the wrong person.”

“I can be independent and still be in a relationship. I’m looking for a partner who wants the same kind of balance of freedom and security as I do.”

“The fact that I haven’t met someone yet doesn’t mean I’m never going to.”

“There are plenty of amazing people out there who are single at my age – like me!”

3. Coming up with strategies and a plan

This is maybe where it becomes a bit creepy: strategies and action plans for meeting someone?! Ick. But we’re not talking about an Excel file here with milestones and targets or following a rigid step-by-step process to achieve your goal of meeting a partner. I simply mean thinking about the kind of partner you’d like to meet (see point 1 above) and how you can make that more likely.

So, for example, you can look at where and how you’re currently spending your time. Are you going to places and doing things that will expose you to the kind of person you’re hoping to meet? Are you open to meeting someone when you do?

When I looked at my own lifestyle a few years ago, I realised that I had been spending most of my time in bars or at home with my coupled-up friends, which effectively gave me zero chance of meeting someone new. Then I started a ‘nomadic’ existence for a few years, where I spent no more than a month in each place, and *of course* this meant that I didn’t allow enough time to get to know potential candidates to find out if there might be *something* there.

Then when I asked myself that second question, about being open to meeting someone, the answer was ‘no’ there too. For my entire dating existence up to that point, my ‘strategy’, if you can call it that, was to avoid eye contact with anyone I was attracted to. This was due in part to my shyness (I just wasn’t confident enough to speak to strangers, let alone someone I fancied) and in part my ego (I didn’t want to admit that I liked someone in case they didn’t like me back). But it’s pretty clear that this isn’t a particularly effective strategy!

So what can you do to put yourself into the kind of context where you might meet interesting people? And what can you do to open yourself up to the possibility when you do? As I soon discovered, a smile and ‘hello!’ is all it takes to start a conversation.

4. Getting the support you need

Finally, and again this can seem a bit foreign, you want to make sure that you have the structures in place to support you in this area as you do in others. In fitness we have personal trainers, in careers we have coaches, in business we have advisors… but what about relationships?

There are relationship coaches out there who you can work with (whether you’re single or in a relationship, for that matter). If that doesn’t appeal, where else can you get support? If *all* your friends are married and at home with their children, how can you meet people – online and in real life – who will provide moral, or practical, support? What clubs and groups can you join? They don’t have to be explicitly for singles, although there are plenty of those. What about a hobby or a sport? If you’re into photography or wild swimming, wouldn’t it be nice to meet someone who shares that passion?

In my opinion and my personal experience, these are four steps that are as effective in the area of love and relationships as they are in career, business, and any other areas of your life. Get clear on what you want, work out what’s stopping you, come up with strategies, and set yourself up for success with the support structures that you need to move forward.

All of this to say:

It’s okay to admit that you want to meet someone.

It’s okay to be specific and picky when it comes to the qualities that really matter.

And it’s okay to show that you like someone when you do.

If you want to reimagine what success looks like in love and in other areas of your life, download this free resource that goes through the 5Ls model – Live, Love, Learn, Lead, Laugh – and guides you in auditing where you are today in those different areas: https://onestepoutside.com/successaudit.

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