What Are You Optimizing For?


There’s a tea house in the heart of San Francisco’s South of Market area called Samovar. It’s known to locals and conference-goers alike for its zen atmosphere, spectacular views, and great grub. I ate there the other day with the founder of Startups.Co., an entrepreneur named Wil, who now owns Zirtual.com. Our conversation touched on a few share-worthy topics I thought those who self-select as Pegasus entrepreneurs or would-be escapee’s of the 9 to 5 may enjoy.

The overlooked, and very simple, bottom line

In talking to entrepreneurs, especially in San Francisco, there is often a pattern of working like dogs towards a fuzzy goal of “massive success”.

The simple fact is we are all seeking happiness. Founders often believe that it lies just beyond the end of the rainbow that is an exit, acquisition, making it onto the 40 under 40, or landing a place on the much-cherished Unicorn list.

But, (spoiler alert) it actually doesn’t!

We are all searching for what we perceive will bring us happiness. The problem is most of us take cues from the external world (tv, magazines, societal norms, social media, religion, etc.) instead of listening to our inner voice, or gut instinct.  

The good news is…

You can be happy NOW. You simply need to know what will actually make you happy (which is often harder than it sounds). So take a breath and think about what’s important to you, give yourself all the time you need… sometimes it takes days, weeks or even months. Once you know what’s important to you, what will *actually* make you happy, start optimizing for it and aggressively cut out the things in your life—especially in your work —that don’t contribute to it..

Here are a few quick steps that can help:

1. Take Inventory of your life, skills, likes and dislikes

  • A great way to understand your top skills for roughly $15 is taking the Strengths Finder quiz from this book.
  • Write down as many things as you can think of that you never want to do again and then stack rank them.
  • As cliched as it sounds, spend a day thinking about what you would do if you knew you couldn’t fail. This question, when taken seriously, can bore down into what your truth passions and goals are.
  • Talk to friends, lovers, colleagues, and others that you trust about what they see as your biggest strengths and greatest weaknesses. (Prepare to be humbled!)

2. Shake free of all external influences, shoulds, and other people’s ideals.

Just because you are 40 and a single woman doesn’t mean you should get married, have a baby, or conform to any of that jazz unless you want to. And if you do, EPIC, go get it gurl. If you want to live in a commune, raise stray cats, and never be tied down, that’s your right too. Don’t feel forced into anything because of age, gender, or societal norms. It’s way less enjoyable than optimizing for what you truly want.

Just because you are running a startup doesn’t mean you should raise money, try to grow BIG, and scale globally in the first year of business. Maybe you and your team will be happier if you never get past 20 people and only ever serve 3 markets. Who knows? It’s worth pondering for a day.

Just because you have a family doesn’t mean you have to raise it in the suburbs. You could raise them on a boat and travel the world.  Other people do it. You don’t hear about it as much because society makes a lot more money on people who do practical things like take out a mortgage, go into debt for a Volvo, and save up to send their kids to an over-priced college.

These are only a few examples, but you get my the drift. There are ideals created by other people and there is what works for you. While sometimes we use the former to guide us, the latter should be your priority.

3. On one single sheet of paper write out your DREAM life.

Think big. Go nuts. Write down anything and everything that comes up. Then start asking yourself why you want to pursue each dream.

Do you want to own a sports team? Great, but why?  Do you love sports and want a place to hang with your buddies while you watch the game? You could probably do that without owning a sports team. Do you want the recognition and social influence that comes with ownership? Fine, but make sure you don’t want that because you think it’ll make you happy. Social status is as fickle as the next scandal.

Do you want to live on a boat with your partner and work in spurts when you’re on dry land?

Do you want to create a thriving virtual community for people like you and have it be your life’s work?

Do you want to be able to financially take care of your family?

Whatever your passion is, as long as it’s not like “I want to wear a skinsuit I made out of the neighbor family,”, it’s fine. If it’s what you truly want and it will make you happy (and it’s not creepy/destructive/hannibal-lecterish), go for it.

4. Find your people

You know when you meet someone randomly, and walk away from the conversation/dinner/bar with the warm, fuzzy feeling of “dang, they are my people”? Whenever that happens make note of everything that happened and the type of person you were talking to..

Were they passionate about pigeons (one of my pet passions… pun not intended… sadly because my boyfriend won’t let me adopt a pigeon as a pet)? Did you spend hours talking about the future of biotech or about hacking physical fitness? Maybe you chatted about your shared love of extreme travel, or virtual entrepreneurship, or living the digital nomad life.

Whatever it is… when you find your people be sure to take note. Keep a spreadsheet on these encounters (in an uncreepy way). Go out of your way to stay in touch with them. One day, when the right project/business/opportunity arises you will have a ready-made pool of your people to rally together.

Just as important as finding the right people are, it’s equally important to know who deal breakers are. Everyone finds certain things obnoxious and annoying. You may not jive with me, I may not jive with you… that’s okay. But for heaven’s sake don’t think you have to spend an exorbitant amount time with people who rub you the wrong way. You don’t have to marry them, take vacations with them, or hire them.

Now it’s time for some reverse architecture

Recently, I did this exercise myself. I spent the last few weeks figuring out exactly what I want in life by journaling, spending time introspecting, and walking in nature (science behind that here).

I realized that the thing I am most passionate about is creating a community for un-tethered entrepreneurs, freelancers, and creatives. Luckily, that’s the exact kind of audience this blog speaks to!

The next step is attracting and exploring the business projects that align with what I know makes me happy. There are a ton of opportunities. I could create a startup that caters to the above, or join one that already exists. There’s always writing as well. Though I believe the best writing is done as a creative outlet without a thought of monetization. Lately the idea of creating a podcast geared towards this community (inspo coming from Mark Maronwe even share *kinda* the same name!), or starting a small conference, has been bouncing around my head.

But remember (and I say this for myself and you my dear reader if you’re going to try out the above), the biggest stumbling block to success is a myriad of ideas and opportunities, not a lack thereof.

Our nature is to go broad versus super-nuanced. Often that is the death knell for gaining traction with a new project or idea. So once you figure out what makes you happy, spend some time thinking of ALL the things you could do and then cut away 90% of them to focus on the few things that will have the most impact on your life. Then simply give those your all.