The fine art of detachment.

It’s been two years since I left the big agency world and started on my journey into entrepreneurship.

I’ve realized now that I’ve learned more in the last two years than in the last decade of my career. Has it been fun?


Fun is not the word I would use to describe the experience.

Character-building. Thrilling. Mind-blowing. Human. Humbling.

I realize now, as I do my round of coffees with colleagues and friends in the industry that they’re most interested in how I’m doing what I do. And it struck me that the lessons I learned could be really useful to other people who have or will walk the same path – coming from a successful career inside a large corporation to building a company from scratch. I’ve started calling it the Outsider Path. There’s a few lessons to share so I’m turning it into a series – call it Postcards from the Outsider. Or maybe Outsider’s Guide to the Galaxy? The Outsider Awakens? 


You get the picture. Let’s get started with the first step that any Outsider must take: learning detachment – specifically detachment from one’s Ego.

Step away from that Ego and no one gets hurt. 

If you’re going to move forward with your new venture, you have to let go of what you were before. Think about it as taking your Ego to the dry cleaners and forgetting to pick it up for all of eternity.

You think you don’t have an Ego? Here’s a quick test for you. Click open the latest kudos piece for your industry - the Top 40, the Mavens, the Rising Stars, you know the kind - and see the face of a former colleague. Oh hello, Ego. Thanks for stopping by.


You will never become a better sales person if you can’t step away from your Ego. 

You say you’re not a sales person? Guess again. As an entrepreneur you are always selling. And selling isn’t an “eat what you kill” scene from Glengarry Glen Ross or Mad Men – it’s far subtler than that.

Excelling at sales, in my experience thus far, is becoming the Best Listener in the World. Reflecting back on my worst sales “moments” made me realize that I thought I was, in my humble opinion, the Smartest Person in the Room. Remember how no one liked Hermione Granger at first? Like THAT. That’s Ego talking.


You need other people. Ego needs to share her toys. 

As a corporate employee you tend to think of yourself as part of a team. The irony is, in my experience, is that being an employee teaches us to put ourselves first. The company’s going to look after itself, so you look after you.

Being an entrepreneur means that you’ve never needed other people more in your life. Accepting, let alone asking for their help means knowing your own strengths and weaknesses, and where other people can truly do a better job than you. Whether it’s a collaborator, a vendor, an employee, your bookkeeper (bless the world’s bookkeepers) they all have something to add and they know things you will never know.

Don’t be afraid to ask a stupid question. Don’t think it’s amateur hour because you don’t know it all. Do share your ideas. Do lean on other people.

Rejection. It hurts. And it’s probably the lifeblood of your business. 

Losing. Failure. Rejection. No one likes it. We spend most of our lives – personal and professional – trying to avoid it at all costs.


When the “worst” happens you have to look at your business and yourself closely and clearly to see what’s not working. I’ll put it plainly. If your business fails, it is your fault. There’s no way not to take that personally. You’re supposed to take it personally – fix it and MOVE ON.

Being in the wrong burns off the Ego. It makes you sharper, better at assessing risks, and a stronger entrepreneur.

And really, you might actually end up liking yourself more as time goes on. Remember how Hermione Granger became the character you'd most want by your side as you fought evil? LIKE THAT.

ThinkingSarah Ivey