1. Weird schedules – Entrepreneurs, especially new ones who are serious, suffer from “Inconsistent Availability”. They never know when they can meet a familial (or personal) obligation because they are regularly available for clients and/or employees.
2. Never clocking out – Many great ideas are born organically. Many entrepreneurs would tell you that their entrepreneurial hat is always on. When you see food on a menu at dinner, they see an opportunity to pitch an advertising idea to the restaurant’s manager.
3. Strange acquaintances – In order to have something you never had, you must do something you’ve never, which includes making new acquaintances, whether male or female. Don’t try to pin down an entrepreneur to only having meetings, calls or doing business with the same sex. Entrepreneurs require freedom in this arena so they can properly grow their business without being so guarded from exploring opportunities with everyone.
4. Odd hours – It’s not strange for an entrepreneur to jump up out of a sleep and start working at 3 o’clock in the morning. (I am actually writing this at 4:33 a.m.) It’s also not strange for them to be taking a power nap at 3 in the afternoon. Entrepreneurs with entrepreneur friends know it is quite normal for them to miss a phone call in the middle of the day and answer one in the middle of the night.
5. Sporadic cash flow – Entrepreneurs won’t always have it like that, even when they do. Smart entrepreneurs spend conservatively in their personal lives to keep the windows of opportunities open in their business endeavors.
6. Missed events – I remember being pressured to schedule traveling to visit family for Thanksgiving one year five states away. I was close to closing a huge business deal that required me to stay local. They couldn’t understand my delay in answering. I refused to give an answer until that deal closed. My family wound up closing their invite before I could close it.
7. Travel – This is perhaps the largest challenge. The world of globalization, coupled with cheaper airline tickets, has created greater opportunities for entrepreneurs but this opportunity has estranged some relationships.