85: Ian Oliver: Getting Back On Top After a Divorce or Serious Breakup

Ian Oliver has advised and guided individuals and families with comprehensive financial advice and money management for over 28 years. During this time, he built one of the largest practices in the industry, most recently starting his own firm in 2004. 

In addition to his passion for and commitment to helping couples transition into the single life, Ian devotes a large amount of time to children-related philanthropy through organizations such as Promises2Kids, Voices for Children and the San Diego Children’s Museum among others. Ian has decided to donate 100% of all profits from this book to these and other selected U.S. based children’s charities.

Ian has been a member of YOP and WPO since 2005 and continues to be an active alumnus of Amherst College and Stanford Business School where he received his BA and MBA respectively. In 2011, he was named San Diego’s Patron of the Year.

Favorite Success Quote

“Communicate, communicate, communicate every day all day.” – Ian Oliver

Key Points

1. Take Time After a Breakup to Understand What Has Happened 

After a divorce or serious breakup, you need to take the time to look back and truly understand what happened.

Not just your side of the story, but what actually happened.

What went wrong?

Could you have acted differently? Were there red flags that you chose to ignore before the relationship even started? Did you know that the relationship was dead for a long time but you refused to cut the cord?

I cannot answer these questions for you.

But if you want to truly recover from a massive breakup, then you must be willing to sit back and objectively look at what went wrong and why.

2. Be Willing to Ask for Help

Divorce is hard.

There is nothing nice, pretty, or easy about it.

And when it happens, it’s easy to put on a brave face and pretend that everything is ok when the reality is you need help. 

This is ok.

Just because you are a man doesn’t mean that you are superman.

There is no shame in asking friends, mentors, and family for help, or hiring a professional.

If you need help to work through your divorce and what happened, then ask for it.

No man is an island.

It’s ok to not be ok.

3. Don’t Focus on the Next Woman too Soon

One of the biggest mistakes that most men make after a divorce is that they listen to the traditional guy advice that says “If you want to forget about the last girl, go sleep with 10 new ones and then sleep with 10 more.”

This is a terrible idea.

When you bounce from a breakup or divorce and immediately try and find the next woman, you are not giving yourself the time that you need to properly understand what went wrong and heal the wounds from your previous relationship.

You need time.

Time to understand, time to be angry, and time to let go.

And if you don’t take this time, you are going to bring all of the same crap and emotional baggage into your next relationship, repeating the cycle until you are finally willing to look in the mirror.

4. Understand What You Really Want 

One of the most important things for you to break down and understand before you move on to another woman is what you really want.

I’m serious.

We all have a vague idea in our heads about what we want in a woman, but how many of us have taken the time to sit down, think about, and write out what we really want.

Beyond just the great body and insatiable sex drive, what are the things that will make a relationship great for you?

Conversely, what are the red flags that you need to watch out for?

If you know what you want before you try and get it, you increase your odds of success tenfold and decrease the odds of ever suffering from another serious loss.

5. You Must Go Beyond Chemistry 

If you want a lasting relationship, you must ditch the emotions and embrace pragmatism.

Ok, so you feel good around a woman.


That will last all of 18 months, and then reality will set in, the emotions will die down, and you will be left with a very real and fallible human being.

So with that knowledge, you must build your next relationship on something more than just chemistry.

I can’t tell you what the foundation is, only you can decide that.

But I can tell you that if you are not building your relationships on more than a fleeting emotion, you are setting yourself up for a life of failure and heartbreak with women.

Build your relationship on a rock so that when the waves and the storm come (as they inevitably will) your house will stand and you will both be able to look at the storm and smile.

Influential Books

Men are From Mars, Women are From Venus by John Gray

Spiritual Divorce by Debbie Ford

Why Men Love Bitches by Sherry Argov


Connect with Ian Oliver


Getting Back on Top

The Times Have Changed. This is the Way Forward in 2024.

Here’s how I can help in my new FREE training on becoming a stronger Grounded Man:

1. The new path for men that creates a purpose driven life and doesn’t require you to lose your personal power, put women on a pedestal or sacrifice your goals.

2. Why men consistently settle and ignore the most important areas of life like the quality of their intimate relationships, social life and happiness and how to optimize all three without sacrificing professional growth.

3. The biggest mistake 97% of men make that breeds loneliness, breakups and emasculation that is absolutely reversible with this counter intuitive strategy.