What 100 Dates in 1 Year Taught me About Business

In the words of the infamous Ice T, “Don’t hate the player, hate the game.”

Let me set the stage for you a little… I was recently divorced (after being married right out of college) and in San Diego, which I’m fairly certain is the land of milk and honey. It’s a beautiful place with beautiful people.

Since I married right out of college, I never fully figured out who “I” was, and when my marriage ended I didn’t really know what to do but to look for another person to fill the void in my life.

So I did what any newly single and lonely guy would do… I jumped on Tinder and Match and began my search. I desired to connect with someone, to feel less alone, so I probably maintained about a dozen conversations at a time (that was incredibly exhausting) and went on a couple dates a week (also exhausting).

I had no clue what I was looking for, but boy was I ambitious… I figured that maybe I’d know it when I found it. (Obviously, this isn’t the best route…)

Now, before we go too far I’ll let the cat out of the bag – none of the 100 dates turned into an actual relationship, and I’m fairly certain that not even 10 of them resulted in a 2nd date.

It turns out that it’s incredibly hard to be attractive, when you don’t even really know who you are or what you’re looking for.

You see, I was really good at getting dates, but really, awfully, terribly bad at developing relationships.

Quality, not Quantity

  • The Dating Lie: I believed that dating was a numbers game… the more dates you went on, the better chance you’d have at finding a quality relationship.
  • The Business Lie: The more clients I could get, and the more projects I could work on, the better chance I’d have at finding good clients.
  • What I learned: Not all opportunities are equal, and every interaction comes with a cost. All the time I spent going on bad dates, or working on less than ideal clients (or on less than ideal projects), ended up taking away time I’d have to spend on the relationship that mattered more.

Be Yourself, not What You Think They Want

  • The Dating Lie: I tried to be the person that I thought she was looking for. If they hated coffee, I didn’t mention my Starbucks addiction. If they weren’t into working out, I downplayed my fitness. I tried to mirror what they wanted.
  • The Business Lie: I thought I needed to have a solution to every problem that someone presented me. If they came to me for anything, it would be bad for business if I turned them away.
  • What I learned: I can’t be everything to everyone… but I can be the best version of myself. In my personal life I have my own unique characteristics, and it’s important that I get to express myself that way. In business, I’ve got strengths and weaknesses… every time I take on a project in my weakness, it prevents me from operating in my strength.

The Goal is to Provide Value, not to Get the Sale

  • The Dating Lie: I (ignorantly) thought that if I could just get on the date, then they’d obviously realize that I’m a catch, and everything else would work itself out.
  • The Business Lie: If I could just take on one project for a client, then that’s all it would take to get my foot in the door for future work.
  • What I learned: By taking on *any* project, or going on *any* date, I was focused more on the short term and not on the long term. Had I focused on being able to provide value first, I would have developed better and more meaningful relationships, and that meant that sometimes I would have to say no to an opportunity that didn’t fit, and that was ok.

Expectations Matter… A Lot

  • The Dating Lie: Everyone looks the same as their profile photo, and acts the same as they did when talking online.
  • The Business Lie: Every project will go according to plan, every client will be a pleasure to work with, and all invoices will get paid on time.
  • What I learned: It’s important to set accurate expectations. The gap between what people expect and what they receive has a direct correlation to their happiness/disappointment. When the gap is in their favor (you over delivered according to their expectation), then people are happy. When the gap isn’t in their favor (you under delivered, of things were different), then people are disappointed. When you set better expectations, you have a better chance at meeting those expectations. When you set no expectations, you risk never meeting them.

Know Your Why

  • The Dating Lie: I needed someone else to complete me as a person, and my value was directly tied to it.
  • The Business Lie: I needed to work because that’s how I’d pay the bills, and if business wasn’t doing well then I must be a failure.
  • What I learned: I get to choose what kind of relationship I want to be in BEFORE I enter into it. I get to choose the relationships that are healthy. I get to choose the relationships that are mutually beneficial. However, It’s not really about me… it’s about how I can impact the life of the people I’m in a relationship with. I can’t effectively love someone that doesn’t like themselves, and I can’t effectively work with someone that doesn’t have pride of ownership in their business.

Seek the Highest Possible Good

  • The Dating Lie: The first date was just a checkbox that needed to be completed. Sometimes you’re in a bad mood and it’s ok to let that show… the list goes on.
  • The Business Lie: Eventually replying to an email is good enough. Being reactive was good enough… etc.
  • What I learned: Every interaction takes effort… why not be intentional and make the most out of it? My girlfriend calls this “seeking the highest possible good”. I’ve been trying this for over a year now (also trying to get rid of sarcasm), and I have zero regrets. You’d be surprised at how much a clearly-stated word of encouragement can mean to someone. When you stop trying to sell (your business, your personality, etc), and you just try to give something of value to others… even if it’s something as little as a smile, or a kind word to your Starbucks barista.


It was a long, frustrating year… I’m grateful for what I learned, but definitely wish I could have learned it another way.

Since that year I’ve sought to do just that… to continue learning.

Except this time, I’m hoping to learn from other people, and not just from my own mistakes and experiences. I want to learn from other business owners I respect. I want to learn from books. I want to learn from podcasts. I want to learn from seminars. I want to learn from online courses.

And hopefully, from all that I can learn how to effectively help others in business, and how to more effectively love in my personal relationships.

The mark of success won’t be measured in dollar signs, but by the value I’m able to bring to the relationships I’m in.