6 Questions You Don't Ask Your Friend Who Just Started A Business

So your friend decided to play Russian Roulette with their future and start a small business. Here's some things you might be inclined to say to them that they'd probably rather not hear.

1. How’s Business?

This is a question that can be understood but not forgiven.

It’s perfectly understandable because your friend just undertook a huge lifestyle change and when you see them, you’re going to ask about it. Not doing so would be like meeting someone for the first time since she had her baby and not asking “How’s the baby,” right?

Well, kind of. Let’s pretend that her baby was born with a defect that has an 80% chance of killing it within 18 months. Cause them’s about the odds your friend‘s business is going to fail. If small businesses were tykes they wouldn’t be the progeny of some 21st century Nordic country with their healthy, busty, sexually experimental populations. No, they’d be stunted, malnourished 14th century children who are lucky if their family can afford to take them to the local barber for a good leaching. Does your question still sound polite?

Okay, but what if business is going well? Look at it like this: your little question is one your friend hears 5 times a day, every day. Imagine how you’d feel if every single day multiple people walked up to you and said something like, “hot enough for you?” Every freakin’ day! So, in the best case scenario you’ve caused eye rolling and come off as trite and insincere.

And that’s the best case scenario. If their business is struggling then you’ve not only reminded them about the hell their life has become, you’ve also forced them to make a terrible choice: be a loser AND a liar and say business is great, or tell the truth and be the Debbie Downer a**hole out to make everyone feel terrible.

2. Do I get a friend's discount?

RedSearcher / Via redsearcher.deviantart.com

Don’t ask this. Ever! Well, at least not until your friend buys a mansion or some other indicator that they've “made it.” Until then please, please, please do not ask for a discount on their goods or services. They are in the most vulnerable stage of a very vulnerable endeavor and every dollar really does matter.

True, a free hot dog from your furry aficionado friend’s new bakery and sausage shop “Bronies, Brownies and Brats” isn’t going to force him to sell his panda costume and call it quits. But you are costing him money because now he can’t sell that dog for full price to someone else. And you’re just one friend this one time. Give one friend one discount once and then it’s hard to say ‘no’ to the next friend.

If you're still not convinced, please look up the definitions of "opportunity cost" and "slippery slope" on google, you cheap, selfish bastard.

3. It must be so nice not having a boss!

It must be, but since this isn't a list about lottery winners it's not relevant. Your entrepreneur friend sure don't know cause she's got the most demanding bosses ever: Clients. Customers. The family and friends she suckered into investing. Her boyfriend / husband demanding to know why she works 15 hours a day 6 days a week and makes less money than a receptionist.

4. Hey, it’s [blank] guy!

Open a business and you're forever defined by it. How'd you like to buy a Volvo and forever be known and introduced as 'Volvo Guy?' "This is Bob. He owns a Volvo! It's boxy, but it's good!" When you open a business, that business defines you to friends from then on no matter how long they've known you.

5. I wish I was as lucky as you to do what I love every day.

Seems like praise, but in fact there's a very good chance you're way off the mark. True, many if not most people start a business because they love the service or product they're selling. But when someone first opens a business, they get mired in admin work. And they also risk making the thing they loved as a hobby seem like a source of stress and resentment. Don't risk rubbing it in.

6. What you oughta do….

Advice is great if it's based on some real insight and delivered thoughtfully. But don't just blurt some obvious solution at someone who's thinking about it 24/7, while you've thought about it for the 10 seconds it took you to spot them and say hi. It makes them think you think they're a moron.

This isn't to say that business owners don't appreciate advice. Sometimes they're caught in the weeds and can't see the big picture or could use a new perspective or are just so exhausted that they've overlooked the obvious. Just find a better way to phrase it.