Craigslist Dating Tips

Relationships Advice


The same strategic planning exercises that businesses use to stay ahead of the competition and maximize profit can be applied very effectively to your dating life. Rather than passively waiting for something good to happen to you, you can take control by applying discipline to the process. First, you clearly define your objective. Then you actively study your target market, your competition, and your personal strengths and weaknesses. Finally, you craft a plan.

The most chilling revelation

As a strategy consultant I wrote hundreds of business plans for clients that included current, 5 and 10-year forecasts. Your odds of getting where you want to go increase dramatically when you know where that is, and map out a route to get there. Because most people amble along waiting to get lucky or trusting in myths like “It will happen when you least expect it,” simply paying attention and setting some simple goals puts you way out in front of the pack.

There’s only one problem – objectives don’t stay the same for 10 years. You’ll grow and change, and your life goals are bound to shift as well. When I went off to business school, I thought it unlikely that I would marry or have children. I wanted a brilliant career in international finance. I changed my mind about two minutes after spotting my husband for the first time. Even if you don’t have a lightning bolt sort of realization, your own plans are bound to shift based on your opportunities, your experiences and your relationships.

How Will You Measure Your Life?

Eric Barker at Barking Up the Wrong Tree discusses a new book by Harvard Business School professor Clay Christensen: How Will You Measure Your Life? Christensen’s book is about using business strategy to manage your personal career, but the principles are easily adapted to dating.

It turns out that 93% of businesses start out doing one thing and changing course because the original idea wasn’t viable.

Professor Amar Bhide showed in his Origin and Evolution of New Business that 93 percent of all companies that ultimately become successful had to abandon their original strategy— because the original plan proved not to be viable.

In other words, successful companies don’t succeed because they have the right strategy at the beginning; but rather, because they have money left over after the original strategy fails, so that they can pivot and try another approach.

The key concept here is pivot. If something’s not working for you, you need to be prepared to change things up. Are you happy in a relationship? Or did that cute guy you liked turn out to be kind of a douche? Not viable?

Time to change direction. How will you amend your strategy? You’ve learned some things about your target market and yourself. How can you put that information to good use to avoid making the same mistake again? For example, you may add the following parameters when assessing a potential mate:

Was shady and vague about his past relationships

1. Texting late for booty call: Not viable!

2. Flaked on plans without good reason: Not viable!

3. Was shady and vague about his past relationships: Not viable!

According to Professor Christensen, companies need both “Deliberate” and “Emergent” plans.

Deliberate is what’s in the business plan, the PowerPoint Deck, the list of goals. And that’s what ends up changing 93% of the time.

Emergent is what you find along the way. It’s when your baby nephew ignores the gift you bought him… but LOVES the shiny wrapping paper. The heart medication research… that ends up becoming Viagra. It’s unintended.

In that sense, things do happen when you least expect them, but you can’t capitalize on those opportunities if you’re mired in “not viable” situations. Learn to avoid the sunk cost fallacy:

In economics, a sunk cost is any past cost that has already been paid and cannot be recovered. For example, a business may have invested a million dollars into new hardware. This money is now gone and cannot be recovered, so it shouldn’t figure into the business’s decision making process.

Or, let’s say you buy tickets to a concert. On the day of the event, you catch a cold. Even though you are sick, you decide to go to the concert because otherwise “you would have wasted your money”.

Boom! You just fell for the sunk cost fallacy.

The Final Words

Don’t throw good energy after bad. Accept failure as a natural and normal part of life – one that promotes personal growth. And then look for new opportunities. Look around you, choose a new direction, and pivot.


What’s rarely required is just more thinking. It’s testing and experimenting that leads to real opportunities.

But it’s rarely a case of sitting in an ivory tower and thinking through the problem until the answer pops into your head. Strategy almost always emerges from a combination of deliberate and unanticipated opportunities. What’s important is to get out there and try stuff until you learn where your talents, interests, and priorities begin to pay off. When you find out what really works for you, then it’s time to flip from an emergent strategy to a deliberate one.

So keep trying, stay flexible. Samuel Beckett said, “Ever tried. Ever failed. No matter. Try Again. Fail again. Fail better.”

There are a lot of boys on the boy tree.