My @ssh*le boss

John, who lives a couple of streets over, is a screenwriter. He's a quick wit and kids around incessantly with everyone he meets. We have a good time trying to top each other to get a laugh.

Today he spotted me in Trader Joe's at the test-kitchen and came up behind me.

“Ugh, I can’t eat that,” he said, referring to my delicious snack. “You know where I can find the tofu?”

I know this store like the back of my hand. “Do you see that lady over there? She's right by it,” I said.

“I have to go stand next to her?” John mock-complained.

“Oh, I’ll protect you! If you want, I can just body-check her into the cheese aisle.” (John is a very large guy who could certainly take care of his own body-checking.)

“Aw, you’d do that for me? That’s nice. So what are you doing in a store on a Wednesday at 2 PM? Do you work nearby here?”

“No, I work from home.”

“So do I!” said John. “The only problem with working from home is that my boss is an asshole,” he chuckled.

“Oh my god, mine too!” I said, going with it, like you do. “She can't make up her mind what I'm supposed to do at any given moment.”

“I know, right?” said John. “Fix the printer. No, wait! Balance your checkbook! No, go make some money…”

I laughed.

“So what are you here to get?” asked John.

I decided to up the ante. “I came here for just one thing. No, two things! Actually, three things!”

“Wow, I hate working for your boss!” he deadpanned.

And it hit me. A lot of us really do have bad relationships with the boss - when we’re our own boss!

It sounds like a punchline - “I hate working for my boss – and I’m self-employed!” <rimshot>

But for a lot of us who work for ourselves, it maybe is kinda… true.

Imagine if you were working a “normal” job and your boss kept switching you to a new project on a whim. Or kept changing the goal line when you got near it. Or nitpicked the work you put your heart and soul into.  

You wouldn’t like that, would you?

Well, don’t be that boss to yourself.

Research shows we prefer working for bosses who appreciate what we are doing for them. Who give us some latitude in how we carry out the work as long as a few clear goals are met. Who can draw a direct line between the work we carry out today and the big picture that we’re trying to achieve in the world.

What would be the number one thing we can do to become the kind of boss to ourselves that we would enjoy working for?


Handling risk - or, what I learned from hurtling down a hill at 45 miles an hour in my underwear with no brakes

When I was a full-time athlete (a long distance inline skater), I took a lot of risks. In races, we often skated down steep paved hills at 40 to 50 miles an hour in just a spandex skinsuit with no protection except a helmet. I thought this made me a risk-taker by nature and that I would take that same approach in business, and that it would be fine and I would rock it.

I found this was not automatically the case.

In sports, the risks are physical, and when you screw up, there’s no mistaking it. You fall, or a referee calls foul, or the ball goes through your hands, or the other person goes over the line first. You deal with it, learn from it if you can, and keep moving.

However, entrepreneurship requires taking a different kind of risk: social risks. If there is harm, it comes to your reputation, your ego, your power status, your relationships. On these goals, you don't get clear, immediate feedback – if you are failing to flourish, it is not easy to find out why.

Therefore, it’s easy to be consistently anxious about how you are doing, whether you are doing the right things, and what people REALLY think. The anxiety can really get you: what if I missed an obvious, important point or perspective? What if I showed my inexperience? What if I am tone deaf?

That’s where it got me, at least. And I found myself becoming so cautious that my anxiety about taking social risks was really holding me back - second guessing myself, wasting time endlessly checking, and keeping me from putting myself out there and going after opportunities to do work I loved and knew I was good at. If you don’t take any risks, you can’t reap any rewards.

Luckily, when I backed off and thought about, I realized there were some ways I could manage the social risks that scared me, in ways that made them more like the physical risks that didn’t.

Here are five ways to make social risks easier to handle:  

1) Think through the rewards of doing the scary thing. Don’t do it just to be a badass. But if you find there’s something scary standing between you and something you really want, don’t go through backflips to pretend you don’t want it. Just decide to practice, learn, and get good enough at it that it becomes a small obstacle instead of a large one.

2) Think through the risks. What is the outcome you are worried about? And realistically, how likely is it? What can you do to lower the probability of it happening? For example, in skating, we might worry about falling on the superfast downhill part of the course, where a fall might mean a broken bone or worse. But that’s not the whole race! That’s just 30 seconds of the race. It is actually less likely that we’ll fall on the big downhill, when we are really paying attention, than on the rest of the course when we are tired and distracted. Those falls aren’t great, but at least they aren’t lethal. So we can train for the scary part - the more skills we have, the lower the risk - but not to the exclusion of everything else that we need to do to get a good outcome.

3) Know the difference between a big risk and a little risk

Most of the things that scare us aren’t really that dangerous, once we think them through. If there’s a big payoff, it pays to decide to start learning how to tackle these every day so they become no big deal. but also visualize the process of getting through it all right, in great detail, start to finish. Visualization is almost as good as real practice and will help you manage your emotions.

4) Find your support network.

When I was skating, I knew that if I turned into a pavement pizza, I could get help. Someone would help me get patched up, and get back out there again. It’s harder with social risks: depending on our earlier experiences, we can feel like if we make a mistake, we’ll be in it alone with no one to help. How to combat this? Cultivate friends who like you for you, and also have some knowledge of what you’re up to. Ask them for honest feedback. Have them with you (or symbolically, with a picture) when you have to do something scary.

5) Think through how to recover if you screw up.

In skating, we used to practice falling on purpose, so if a fall became inevitable, we could do it without hurting ourselves too much and get back in the race. Now, for social risks, I make an if/then plan – for example, if I say something stupid on social media, I will apologize and/or follow it up with a joke that someone from my support system friend has ratified.

Sports taught me that taking risks was not just okay, but the only way to excel. Physically safe? Maybe not. But the sports mentality has given me a good model for analyzing the risks that scare me in my business pursuits. Now when it’s time to take risks, I try to remember these five lessons and get through it with a smile.


Having your sh*t together

You know what? A lot of the time I don’t have my shit together. You know what else? Neither do you.

Some people who know me will read my statement about myself and say Ha! Kim, you’re so organized! You’ve got spreadsheets and you’re prepared and present. Others will read my statement and say, Hahaha - yup.

A lot of my clients believe that if you don’t have it together, you can’t be trusted to be in charge of something.

That is, if you don’t always show up on time, perfectly coiffed, and fully prepared after eating a balanced breakfast and planning for every possible traffic tie-up, that if you don’t believe 100% in the ideas you are presenting and haven’t done your homework down to the names of your client’s six grandkids, that if you don’t have perfect credentials and a custom designed website and always return your emails within 24 hours and never procrastinate, cry or doubt yourself - then you don’t have what it takes to do whatever it is you are trying to do.

And you know what? That’s utter BS.

You would be surprised at the level of accomplishment and success I have seen from people who clearly don't have their shit together at all.

I watched a client absolutely crush a meeting and seemingly play at the top of their game, with enthusiastic yesses all around.

Then when I complimented them, they admitted embarrassedly that they meant to prepare earlier but didn’t get around to it, so they were going to do it last night but their son was throwing up, so they slept like shit and only rehearsed it this morning while driving to the office, and they spaced on the main client’s first name 15 minutes into the presentation and suddenly they remembered they had not updated the graph on page 6 so had to find a way to skip over it on the fly, and there was a big hole forming in their tights which they hope they stopped with a dab of nail polish in the bathroom before the meeting, and the client asked about something they had meant to research but forgot about….

What things look like from the inside and what they look like from the outside can be two very different things.

Where do we get the idea that our habits have to be perfect if we’re going to do what we want?

Because it’s all around us. It’s a cultural message. Pick up any business magazine and see the tough talk: You’ve got to be on your game, master the details, set habits for success, don’t let them see you sweat.

But the fact is, very few people really operate like that. Some of most “successful” people you know are still sweating and failing and oopsy-ing every day. They miss details. They get depressed and can’t even. Their family lives are unpredictable. Emergencies come up. And that means tomorrow they will scale back or move the deadline or miss the deadline or farm it out or basically do something other than stay up all night to get the job done no matter what, even though that’s what the business magazines would have you believe is always the right thing to do.

And still it will all get done in the end.

Yes, it’s true that less chaos would be objectively “better.” Sometimes, if your life is messy, there are consequences. Some business settings do reward style over substance. And some people are so chronically chaotic that you do walk away from them going, Oh. My. God. No way I’m getting involved with that.

But other people – if I’m honest, I’d say most people – manage to be in a fairly constant state of chaos and still be the boss, gain the respect, or even just have a lucrative-enough career doing work they find meaningful.

What’s the difference between the people who make the chaos work well enough and those who don’t? I see 3 main differences.

1)   People who make it work don’t let the fact that they don't have their act together stop them from putting themselves out there anyway.

2)   They don’t advertise it. Their inner circle knows what’s up, but they are self-aware enough to have a good game face on hand for the people whose trust they have not yet earned.

3)   And this is the most important one: They accept themselves 100%. This doesn’t mean that they don’t review how things are going and take steps to improve where they can. It just means they have stopped spending their energy trying to fix themselves to look more like the vaunted ideal of professional productivity, and instead focus their efforts on doing what needs to be done, even if it’s a complete clusterfuck.

Now that we all know that you don’t have your shit together (because no one does), what can you do today to focus on self-acceptance?  

I'm not sure and I'm not sorry

Much has been written about women’s tendencies to overuse the phrase “I’m sorry.” I’ve never been big on apologizing, but I have noticed how much I use “I’m not sure” and “I don’t know.” To be sure, there are plenty of things in this crazy world to be “not sure” about. My scientific training only magnifies this tendency to see life in its many layers, possibilities and viewpoints. 

But that’s not what I’m talking about. I’m talking about the times when I’m actually damn sure –and I’m also damn sure that it would not go well if I said so straight out.

“I’m not sure I can fully support that,” I say – but what I mean is “Oh, HELL no!”

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Robots don't need our praise

The day Apple introduced Siri, the iPhone-based personal assistant who responds to your voice, I was having lunch in San Francisco with some clients and we were all playing around seeing what Siri could do.

 “Siri, what is the weather like outside?”

 “It’s cloudy.”

“Thank you, Siri,” the CEO said.

“You’re welcome,” said Siri. Then we all burst out laughing.

“Dude, why are you thanking a robot?” joked the SVP. The CEO looked sheepish. 

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