Truth: for a long time my family had absolutely no clue that I got paid (In actual money? No way!) for what I do for a living. In fact, I think that a lot of my family members still think that I live in a hole in a wall NYC apartment and am riding the system – even though I make more money than my husband who has a full time salaried job. I am a full time freelance writer and own a blog and left the corporate world back in 2013 to pursue those dreams after being laid off – for the second time.


Taking the plunge into being full time self-employed is hard emotionally and financially and is effing scary. Most people don’t really get what it’s like to start your own business and until it takes off and becomes a well-oiled machine (ahem, putting money in our pockets), the slightest comment can make or break our day.

So if you have a friend who is an entrepreneur and going for a rough time, here’s how to encourage them without pissing them off.

1. Don’t give advice unless we ask.

I can’t stress the importance of this enough. Whenever we’re chatting and you offer advice for a problem that we’re having, I promise, it’s only going to frustrate us more. Just lend your ear.

Just be a sounding board and listen to our struggles, sometimes we just need a pair of ears to ramble on and on to. And most of the time, we need to figure out our answers all on our own.

2. Be there to listen, but don’t pretend to understand.

Listening is one of those most encouraging things for women because it lets us know that we are cared about and that you are honestly interested in what we are doing. But all of that can be quickly tarnished when you pretend to understand that you know our woes – especially if you haven’t actually walked a mile in our shoes. Just be a sounding board and listen to our struggles, sometimes we just need a pair of ears to ramble on and on to. And most of the time, we need to figure out our answers all on our own.

3. Let them know how proud you are of them.

It’s so amazing how far the statement “I’m proud of you” can really go. It is so powerful to hear those words from someone that you look up to in life, especially whenever you might be having a business setback. Take the time to let your entrepreneur friends know that all their hard work doesn’t go unnoticed and how much you are in awe of that they accomplished. This will probably be just the inspiration they need to push onward.

4. Treat them to a pedicure.

Or treat them to any equivalent to a pedicure. I had an experience many moons ago whenever I was out with another female entrepreneur friend who was much more seasoned than I was and she wanted to stop and get pedicures together, spur of the moment. At that time, I barely had two pennies to rub together and knew my husband would kill me if I charged it. I told her my situation and she happily treated me to my pedicure that day. Why? She told me that she knew in a couple years from now I would be treating her when we were out together, and she was right.

5. Bail them out.

Whenever your entrepreneur friends fail, (and they will) bail them out. It doesn’t have to be financially bailing them out, sometimes just a visit with wine in hand will do. Bailing them out lets them know that you are on their side and championing them no matter what happens.


WRITTEN BY

Allison Cooper