Married to Your Business: Dating and Relationship Advice Your Partner Wished to Give You.

Olga Skipper
5 min readJun 23, 2023


Exactly 8 years ago, I found myself in Bali as one does when you are a 30-year-old ambitious serial startup founder that had just left one company and hasn’t started the next one. To entertain myself, I booked a palm reading session with a medicine man called Ketut from Elizabeth Gilbert‘s Bestseller Eat Pray Love. During the ceremony, he looked at me with his famous smile and said: “You know, Olga, you are going to have two marriages in your life: a short one and a long one.”

Funny enough, exactly on that day, I finally stepped out of my short one.

When he told me his prediction, I knew he was right - I wanted to re-marry. I knew I wanted to try it all over again. I just didn’t know how am I going to make the second one — the long one, knowing everything I knew about myself. That I am a driven entrepreneur that spends tons of time building things, and I am aware of how different I am from many people around me.

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I gave it all to the previous relationships, all I could give, and now I was questioning what the hell went wrong and, if I am about to start my next relationship, how to improve it. Is there someone out there who can keep up with my speed, my single-focused life of building companies, and my personality? Or do I need to change and give up who I am?

The “Founder’s Spouse” Syndrome

To figure out whether this topic is even relevant, I asked my audience on Instagram whether this topic of the founder’s relationship with their beloved one is something of interest. I usually get an answer or two, and that’s it. This time more than two dozen of women rushed into my DMs, telling me that I should raise this topic.

Some of the ladies were quite angry; some were curious to understand their partners better and share their experiences of dating founders. And both groups were puzzled. Life didn’t prepare them to be an entrepreneur.

The life partners that spoke to me openly shared that they feel devalued and feel that if they are not “delivering and performing” or are not entrepreneurs themselves, founders are not listening to them. They also felt alone. Quite often, the only one at family gatherings, at social events, and just at home. By themselves. They felt forgotten.

They also felt that they are a part of the founder's support team, an employee of their enterprise, not a soul mate. They felt that their relationships were on the brain-brain level; they felt disconnected from their partner and not loved.

(It is not purely a male-female story. I see it happening with founders of any gender. There is more complexity, though, when it comes to women, but that will be my next piece.)

Lonely and Successful, or Not

There is a certain point in time when every entrepreneur asks themselves the same question that I asked myself back in Bali during the palm reading: am I even made to have deep connections and lasting relationships while being true to my nature of being an entrepreneur?

I strongly believe that the answer is a definite yes. We can. The question is more — what kind of an inner dialog needs to happen for a founder with themselves, and what decisions need to be made out of this dialog?

Imagine a very generic founder of a very generic company coming into my coaching space. Imagine them sitting down in the coaching chair, looking at you as a partner in crime and may be the only person who is really there for them at this moment. And you ask them to start talking, and they are fully open to sharing. Here is what you might hear.

“You know, I am exhausted. It has been a rough couple of years, and I gave it all to the company and building my business. I had to put all my focus and all my attention into making this venture take off. And it was never enough. I see people around me succeeding and being on the top of the pyramid, and I am not there. I feel I am failing. I am failing every single day. I am failing to be a good father, a good partner, and a good boss. I thought I could do it all, but now I just think that it would be easier for me to be alone in order to succeed”.

Those people I see around me, those founders, have a rough time. They crave connection, yet connection with their beloved ones is really hard for them. So they start prioritizing what they do best — work, and they move relationships into a subcategory under work. They schedule slots in their calendar to “meet” their children and spouses; they are “managing the family”, outsourcing, delegating, and giving money to everyone cause money means love to them and might be the only way they can connect to others.

The Connection

The truth is though that to gain connection you first need to gain it from within, not from the outside world. It is close to impossible to connect to others if you are so afraid to connect to yourself.

The subconscious of an entrepreneur knows that risk — that if they truly and deeply connect to themselves, they might see the real world around them. The pain they hold within themselves, the sadness they carry, the exhaustion, frustration, anger, and lack of joy. And it might 1. slow them down, 2. destroy what they’ve built, 3. question their life choices.

Their identities are wrapped around them being entrepreneurs and around the competition and the pressure they are facing. So even if they are in-between companies, it is very hard for them to slow down and recharge. Because switching to “rest and digest” mode is also a skill that they’ve lost while achieving.

There is Hope

I don’t want to end this piece on a gloomy, sad note because this is not how this story ends.

There is a group of founders that I meet now more and more often. I call them the founders living in a 5D world. Those that managed to transition from being a single-focused entrepreneur and realized that the 2D life that consisted of just work doesn’t fulfill them anymore.

That transition usually starts as an unpleasant surprise: companies fail, they get fired from their own startups, the economic situation changes so drastically that what they’ve been building becomes redundant, their life partners leave them, or their children don’t connect to them on the level they would wish for.

They describe that moment as the moment when they start noticing that putting all eggs in one basket — meaning covering all our needs for the emotional connection, acceptance, recognition, etc. hurts their work or limits them in what we truly can achieve.

In order to rise again, they had to do some deep inner work to reconnect with themselves and learn to recharge. And they do rise again. That transition IS possible.

Throughout the article, I left you some links to chew on. Do that. If you are a founder that experiences this transition firsthand, please feel free to reach out

I would be more than happy to talk.

love you,




Olga Skipper

Executive coach and Advisor for Tech Founders and Entrepreneurs. Asking uncomfortable questions.