Why Entrepreneurs Suck at Relationships (& 4 Ways to Get Better)

Starting a business is hard. Having a healthy relationship is hard.

Unfortunately for many entrepreneurs, we suck at balancing the two.

And by ‘many entrepreneurs’…that includes me.

The Break Up

My last relationship didn’t end well. I was deep in the midst of getting started on my entrepreneurial journey. I wouldn’t surface for hours from courses, books & the computer screen. I felt possessed with purpose. She said I’d changed. She was right.

Of course, I was oblivious to it at the time, but it was clear what my priority was. She felt it. Got jealous of my new priority. I thought she didn’t understand. The wheels started to come off the bus. We broke up.

So I was single.

I worked long hours. I was driven to ‘make it’, working every weekend and late into the night.

When you want to succeed as badly as you want to breathe, then you’ll be successful’ I would hear Eric Thomas shout in my ear.

When I did have time off, I was so emotionally and physically drained that I didn’t want to go out and socialise.

I felt that anything but absolute focus on my making it wouldn’t be enough. How could I have time for anyone else?

Bit like this guy:


With an attitude like that, I was undateable.

On the few occasions where I would be out with friends, they’d ask me if I had anyone in my life. I’d brush it off telling them I was ‘too busy hustling’. I wore it with pride as if it was something to be proud of.

If I did meet someone, it would invariably flitter away. We never seemed to connect (in the 10 minutes I would spend texting her between my emails once a week). I wouldn’t open up, no time for that.


I’d love to tell you that because I was so focused on my entrepreneurial dream that I was immune to feeling lonely, or wanting a close connection with someone.

I wasn’t.

When I was busy I was fine. The busyness numbed my emotions. But when I had downtime I felt lonely. So I kept busy. That’s ok because luckily I had a to-do list that went on FOR-EVER!

Entrepreneur Problems

Entrepreneurs are not normal. We choose to walk away from stable, well-paid jobs to start a business that statistically has a low probability of success for little or no pay.

Never do we know this more when our buddies WhatsApp us from the pub on a Friday night to ‘come down for a jager-bomb’ when we’re spending the evening googling ‘what is CSS’ trying to fix that button on our website.

The Entrepreneur Dilemma

I believe things that make entrepreneurs good entrepreneurs: single-mindedness, drive, and relentless passion & focus to bring our idea to market: makes many of us inherently more difficult to have relationships with for those same reasons.

It certainly affected me.

I used to fall into this ‘black hole of focus’ where nothing would snap me out of it.

I remember wondering if I would ever have a relationship again.

Then I changed

Then I met someone.

Boy meets girl. Her name was Stefie.

My biz had raised venture capital investment and we were sure we were we were on our way to becoming next unicorn. She’s been on that rollercoaster with me the past few years.

Then, about 18 months ago Stefie launched her own business that is growing incredibly fast. I’ve also been on the rollercoaster with her. We’re at different points on the rollercoaster ride, but together at the same time.


Given my past relationship experiences, I was determined not to feck this one up.

So I approached it like I do most things in my life. I start with the assumption that I’m not very good at something, I find role models who I can learn from and then learn what I need to do to get better at it.

I believe we can learn anything and get good at anything in life if we distill it down to the daily habits that we do every day to put us in that path. I figured relationships should be no different.

In this post, I’ll share the four things I learned and use in our relationship that has helped us have a happier and loving relationship than I ever thought possible.

Who is this post for:

This post is for entrepreneurs who are just starting a relationship and don’t want to screw it up. Or are in a relationship you truly care about and want to get better. If that’s you, my guess is that your personal drive has probably already caused you some problem with intimate relationships in the past.

I know because I did.

4 Healthy Relationship Habits for Entrepreneurs

Relationship prority


Entrepreneurs are incredible at planning. We will spend hours strategising our visions. Going on management away days. Doing quarterly planning. Reading books from Drucker to Allen on how to plan and get stuff done.

How much time would you spend to plan and prioritise your personal life?

If you were anything like me. Zero time.

My average week would go like this: I would plan out my work week, write out all my actions to hit my business goals. Only then relationships would I look at personal life. I’d keep a few good intentions in my mind about what I’d do, without any firm actions.

The week would go by in a flash and it would be Sunday again. I didn’t do any of the things I had ‘good intentions to do’ in my personal life.

So let’s replay that….

Why did I write out my business plans for the week? Because I know I am more likely to do them if I write them out.

So the items in my business are important enough for me to write out my plans for the week, but my personal ones were not?

So step 1 is, we need to get our priorities straight.

Truth is: You can have only one #1 priority in life.

Priority is a singular word, not plural.

The first step is to make a decision on what the no.1 priority in your life is. Is it your business or your partner?

‘but my business and career is so important to me’, I hear you, I get it.

Answer me this: Would you want a long-term relationship with someone if you were not their no.1 priority?

Guess what, I doubt the other person does either.

Decision time

So make the decision. Is this person your no.1 priority?

If not, cool. I’m not judging.

If so, treat them like it is.

How I do it:

For me, it all started with this decision.

A little while after knowing Stefie I decided that (said in an Irish accent) ‘ah sure she’s grand’. I consciously made the decision that she would be my no.1 priority.


Not no.1 alongside my business, Liverpool FC & my stamp collection.

No. 1.


No.1 Stefie (family)

No.2 My business

No.3 Friends

This makes decision-making easier from then on.

Goal Setting

When I set my goals every year I make sure I include my no.1 priority. My number 1 goal (out of 7) for 2016?

Goal 1: Make Stefie my number 1 priority every week. Here’s the actual screen grab from Evernote:

Evernote goal

This is important as I remind myself of my year goals every week when I’m planning my week.

When I plan my week every Sunday evening, I open up my yearly goals in Evernote and for each of my seven goals I ask myself:

Q 1: What did I do last week to make Stefie my number 1 priority?

Q 2: What will I do next week to make Stefie my number 1 priority?

Take action:

Ask yourself the following questions:

What’s your no.1 priority?

If your priority is your partner, how are you going to show them that this week?

Common question:

But Howard what happens when you need to do something important at work and it conflicts with something you and your partner has planned? If he/she is your priority, do you cancel work every time?

Of course not…I cover this in the next point.

Relationship bank account

2. Relationship Bank Accounts

I read once that relationships are like bank accounts.

When you spend quality time with someone, do nice surprises, go on trips together etc. you make deposits into the bank account.

When you work late, cancel dates, miss plans. You withdraw from the bank account.

Like a bank account, you can build up savings or you can go into the red.

A healthy relationship will have lots of savings in the bank account.

An unhealthy bank account will be in the red. This is when issues will begin in the relationship.

I like this way of looking at relationships and I try and follow this principle

As a simple rule, always look to make deposits into the bank account very week so if something comes up and you need to make a withdrawal, you won’t need to go into the red.

This bank account principle is a simple way to look at relationship health. If you’re depositing every week into the account, the relationship is usually healthy. If there are issues, it usually stems from an overdrawn bank account issue.

How I do it:

We both understand the relationship bank account principle and make sure we make regular deposits in our bank account every week.

We do this by making sure we spend lots of time together. For us this means:

  • Spending every weekend together (not working)
  • Getting in some playtime every weekend (we like going to walks and museums, whatever works for you)
  • Going on regular holidays (we love walking trips down the countryside, & staying in an Airbnb. It doesn’t need to be expensive)
  • Weekly dates nights (more on the latter in the next point)

Take Action:

  • How healthy is your relationship bank account?
  • How can you make a deposit in your bank account this week?

Date night

3. Date night

Although a similar principle to the ‘relationship bank account’ I mention above. I believe this warrants its own point.

If you do nothing else but implement this one thing; I believe it will significantly improve your relationship.

I know because it has for us.

A few months into our relationship, we created date night.

Date night is a mid-week evening every week that we go on a date together. A ‘date’ is doing something special: theatre, cinema, meal, picnic, long talk, museum late, dancing class, board games night…you get the picture.

Doesn’t need to be expensive (a bottle of wine in the park is one of our favourites), it just needs to be thoughtful and just us.

So NOT the new sci-fi movie on Netflix and UberEats (trust me, I‘ve experimented with this and can confirm it is NOT a hit 😉 )

I’m sure most of you have heard of having a date night before, maybe taken one or two yourselves. But ours has one key difference: it’s in our diary as a recurring item every week.

And this is the reason it’s so powerful. It’s literally a date in your diary every week. So when things get busy, fires start in the business it’s easy to get distracted you know you have a minimum of one special night together midweek. It makes all the difference.

Nothing gets booked in over date night.

How I do it

For date night I set up a recurring calendar

I can only speak for men here, we have the best intentions but when important things come up in the business we get sucked in.

Setting up a weekly calendar invite does the heavy lifting. It’s a placeholder so you know an event is on without having to arrange it every single week.

So I literally sent a recurring calendar invite to Stefie for every Wednesday night

Date night calender

Then we take turns in the date night. One week one person organises and pays for the other person. The next week the other person does it.

So twice a month you need to think of something fun to do and pay for it. Not too bad eh?

Take Action:

Send a calendar invite to your partner for date night.

Ninja tip: She will naturally ask you what it’s about.

DO NOT SAY: I read this blog post and thought it would be worth a try.

Do say: You’re my no1 priority and want us to make sure we have some fun time together every week, even if we’re busy.

= Maximum brownie points!

Taking off the mask

4. Taking off the mask

Guys like to look strong & tough. Therefore we don’t like to show any weakness or say we have any problems.

The problem with this is, of course, it’s complete bullshit.

We don’t want to open up and speak to people about our problems as we believe it will make us look weak. If we look weak we believe we won’t be loved.

I believe this is the big cause of why so many men suffer from depression.

And by not opening up to anyone, this includes to our partners.

We wear a mask

By not opening up and putting on a strong front is like putting on a mask. This mask allows us to project to other that we are someone strong and has it sorted.

When behind the mask often we don’t feel the same way.

How to connect

I believe the only way to truly connect with someone is by taking off your mask and let them see what’s behind it.

This means taking off your mask and being vulnerable with someone. That means talking to them about the things you don’t want to talk to them about.

Yes, those things.

So the way to have a deep connection with your partner is to open up and be vulnerable with them.

Tell them the things you’re afraid to tell them because you think you’ll look weak. If you do this you’ll connect with your partner in a way you never have before.

It’s literally life changing.

How I do it

I remember a few weeks into going out with Stefie, I decided to open up about some things in my past.

I was petrified. I built up to that moment in my head for weeks. I couldn’t look her in the eye when I spoke to her.

Of course, the things I had built up in my head as being a huge issue, were not such a huge issue to her and they didn’t faze her in the least.

My opening up to her allowed us to connect in a deeper way than ever before.

When I haven’t taken off my mask with people in the past, the relationship has never gone further that surface level.

That opening up grew my confidence to do so more regularly. Now I try to open up as often as I can with her.

We long for connection

I believe we all long for deep connection. You can have this by taking off your mask.

Take action:

What’s the thing behind your mask that you don’t want to tell your partner?

Try speaking to your partner about it.


In this post, we’ve talked about how many entrepreneurs struggle-having relationships.

We’ve discussed some habits that we can help us overcome our entrepreneurial tendencies to have loving relationships, without sacrificing our goals or businesses.

Your turn:

What habits have helped you in your relationships Please share them in the comments below.



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