October 3, 2013

16 Truths About Being Your Own Boss. ~ Jordana Halpert

Photo: ThisIsRobsLife

Our society celebrates the entrepreneur—most people jealous of the freedom that they think comes along with it.

This idealization of self-made people was created because sadly so few of us speak honestly and vulnerably about how it feels to start your own business.

The truth is it can be hard to speak up about what it is like when no one in our life knows what we’re going through.

So I’m coming clean. Unapologetically.

I don’t want to turn anyone away from starting their own business—hell, I suggest entrepreneurship to everyone. I just think it’s important to be honest about it. Being an entrepreneur isn’t always shiny and whimsical. It is immensely satisfying, yes. But with that comes some pretty intense gremlins whispering in your ear.

That’s the balance of life.

I know not all of us have such a dramatic start-up, but I also know how many businesses don’t make it past three years. There’s a reason for that.

I want to share my truths so no entrepreneur thinks they’re alone—so the fear we feel doesn’t consume us into quitting. So our paycheck friends and partners can understand what we are going through.

And maybe (just maybe) we can raise the baby we call a business into a fully-grown success story, changing those stats for the better.

1) It feels like we can’t say anything.

Most of us are faking it until we make it when starting our own business. Trying to play it cool and nonchalant when we land our first client—then go home to jump for joy in privacy.

We buy only ‘expensive’ looking clothes from H&M and cut out the labels in an attempt to seem successful. And when anyone asks how business is going, we tell them it’s booming, even when it’s not—just to protect our brand.

At times, we may resent our own ever-positive Facebook posts and stop posting for a week or a month because it feels like a lie.

2) We fantasize about getting a ‘real job.’

Every human has moments where they remember only the good stuff from a past life. Just like the terrible ex-partner we idealize, the reliability of a regular paycheck is incredibly alluring. That haunting desire to work for ‘the man’ again can feel never-ending.

3) Partners are saviors.

From paying the cheque at restaurants to covering your grocery bill, life can be a lot better when in a relationship and starting your own business. I have immense respect for single entrepreneurs because I’ve been there—and it sucked.

From dollar-store soap to pasta every meal, it was a lot like dorm life without the honesty about living frugally and parents to bail me out. And that life is a lot harder at 30 than 20.

4) Business friends feel like best friends.

Some of us are lucky and have a few entrepreneurial friends to talk to over an expensed lunch. Business friends know what we’re going through, and what’s better, they may have the perfect book or program to lift our spirits back up.

It’s a comfort that paycheck friends just can’t provide.

5) Money makes us crazy.

I believe there are foundational things in life that will shatter well-being if taken away. Money is one of them. Craziness is inevitable without confidence in where or when the next dollar is coming in. Ask my boyfriend about how I reacted every time he asked if I was paying rent that month and he will tell you I was straight crazy.

I won’t even begin to tell you what it’s like to split the bill when everyone else has been drinking and ordering appetizers, and you carefully ordered the one meal your bank account could afford.

It’s something like a shame sandwich.

6) Low Seasons are not a vacation.

We all read the business books and fantasize about working from the Caribbean via laptop in a hammock, cocktail in hand…but then down season happens, and panic sets in. Spare time feels like torture when it isn’t by choice; one bad week and we think our business is failing.

It’s the furthest thing from vacation.

7) Every few months you will look at your website/branding/business cards and realize they suck.

Things change once we’re out in the world; as the needs of clients evolve, our services do too. It’s entrepreneurial evolution. And if that doesn’t happen, then someone else’s amazing website makes us doubt our own. Rebranding is inevitable.

8) Other people are always doing the same thing, only better.

I know grandma told us this at age five through fifteen…but living it is different. Branding yourself is a damn vulnerable place to be.

We only hope at some point we can learn to be inspired by these ‘better than’ people, instead of beating ourselves up.

9) Free webinars are rarely valuable and are always selling something.

Oh, the free webinar. There are so many of these that we could (and probably will) fill our entire workweek with and they all say the same thing: Buy my program.

10) Believing more training is the key to success.

We crave taking more courses to be in the mindset of learning, not to gain knowledge. The real growth comes from failing, then having the balls to stand up again and learn from our mistakes. And until we do that a few times, we sure as hell won’t know which course is the right one to take.

11) Working in pyjamas isn’t so great.

Productivity hits a remarkable high when I get dressed before breakfast. Work environment affects us and dressing up to leave the house does wonders for the confidence. There is a reason there are so many coffee-drinking people on laptops at your local cafe.

12) Netflix is the enemy.

A client cancels and/or a nasty comment hits on our Facebook page and we might succumb to a binge of terrible shows on Netflix. This is also the hardest thing in the world to avoid because in the beginning there is really nowhere we have to be. We pretend to be sick while Instagramming pictures of tea and tweeting about taking a “lovely and well-needed day off”…when in reality we are wallowing in self pity, eating potato chips and lusting after clothes to buy on Etsy once we have ‘made it.’

13) When a client stops our services, it sucks.

Having to be understanding in this circumstance is the hardest thing for an entrepreneur to do. Even successful ones will tell you that feeling doesn’t go away. It just gets easier to bear. And it’s not that we don’t understand our client’s reasons- the worst part is that we do. But being understanding when you’re disappointed is the worst.

14) Free first-sessions are the best…until they’re the worst.

Don’t get me wrong, I actually think it’s important to give your services away for the first few months of starting a business- it grows a network and experience, and gets us in touch with the work we left our job for.

Just don’t do it for too long.

There’s a fine line between learning, and giving too much shit away for free. That’s when it gets hard to ask people to pay for services, and sharing our rates becomes a question (not a declaration). ‘Free’ gets no respect—people love to cancel free sessions last minute.

At least a full day of $10 first-time clients means not eating Kraft Dinner every meal.

15) Just because someone’s on televsion, doesn’t mean they’re successful.

We “ooh” and “aah” at the entrepreneurs who get featured as guest experts on local morning shows and dream to be them one day. But the truth is that most people don’t get paid to be on television. The shiny ‘experts’ we lust to be are likely in the same boat as us.

This desire to put someone on a pedestal is not the way to success; the most successful entrepreneurs are often the ones we least suspect.

16) At the end of the day, we love our lives.

This is the truest of all my statements. When I leave a session with a client, there is no feeling like it. Having someone’s life change because of a conversation with me is the greatest feeling in the world. Hands down, it makes everything worth it.

The truth is entrepreneurship can be pretty lonely. Working alone is not something that is in our blood. We are tribal animals, and pack mentality will tell us at any given time that being different will get you killed.

But it’s not the truth.

So if you have a friend who is an entrepreneur, give them a hug. Tell them you are proud of them.

It is hard to be your own boss and that one like on your friend’s Facebook page could be just what they need to keep them going that day.

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Jordana Halpert