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3 Questions 'Always On' Entrepreneurs Needs to Ask Themselves…

We hear it all the time. The grinder, the hustler, the go-getter. That person who never quite pipes down about what they are doing and where they are doing it.

“Why must you sell the waiter on downloading your product?” “There’s always an ‘ask’ with you, isn’t there?” “Okay, it’s Christmas — can you stop selling today of all days?” If you’re an entrepreneur, you’ve probably fielded at least one, if not all, of these questions throughout your climb.

When you start a company, you must be your own best advocate. You must sell to everyone and boast every day. If you won’t, who will?

Related: 5 Warning Signs Your Business Is Killing Your Relationship

As I define it, the “entrepreneur’s dilemma” is the choice you, as an entrepreneur, are faced with each and every day. Do you stop selling everyone around you for the sake of your friends and family? Does it make you a better friend or family member if you do? There are three specific questions to consider when faced with the entrepreneur’s dilemma:

Should you turn it off for your friends and family?

I recently met with a friend who afterwards said she felt the meeting was just smoke and mirrors. She said she felt duped because all I was doing was talking about my company. I could see where she was coming from, and I felt a little bad at first.

After talking it out with her, I said plainly: I work 16 hours a day for my company. I don’t take vacations because I can’t afford to take the time away. My relationship is constantly being strained due to the fact that I’m always plugged in. I am constantly putting out fires at all hours — day and night. So, frankly, the updates on my life essentially ARE updates on my company.

Try to be more cognizant that although you may not have a life outside entrepreneurship, your friends do. If they’re real friends they’ll expect you’ll tip-toe the boundary line, but try not to sell them off the bat (it was shamelessly the first thing I said after hello).

Related: 13 Characteristics of Successful Hustlers

Can you even turn it off?

We spent last Christmas with a few friends. When my friend and his wife were video chatting to his family, the front-facing camera panned to me. What did I do? I started in on my elevator pitch and convincing them to download my product. I’m guilty of taking any opening I can and running with it, segueing into my company somehow, someway.

You may have to be “on” for 360 days out of the year, but if nothing else try to reserve holidays and a few other special occasions. Tell yourself, “I’m not going to talk about it at all while I’m at the science center with my family.” Try making it a point to be as descriptive as possible in your calendar when scheduling the time: “30-minute hike with Mike Ryan, don’t bring up XYZ Co. right off the bat.” Sometimes the visualization will become self-actualizing. 

Related: My Career in Silicon Valley Taught Me the Futility of 80-Hour Work Weeks

Most importantly, are you doing yourself a disservice if you do turn it off?

In a world where you only need one person to believe in you; that one person could be THE person. The person that can make the difference to your company. You never quite know who could be that person. It could be the person you just passed on the street, that you met at a networking event but didn’t talk to, that person sitting at the bar nursing a drink, that gal at the coffee shop writing her screenplay (I live in LA — this is what 70 percent of coffee shops are used for). If you want to spread your story, your brand, your product, you must always be “on.” You constantly must be in selling mode, otherwise you could miss your chance.

This is my perpetual fear. The fear that I will knock on 1,000 doors and I’ll stop, and unbeknownst to me, my opportunity was behind door 1,001. Opportunity doesn’t knock — it answers. You have to do the knocking.


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