During last month’s workshop on dispelling legal myths and fears, one thing Rebecca said that really struck me was how creative entrepreneurs tend to be optimists.

It struck me because I think it’s true.

And yet it’s not.

Let’s face it. We’re a pretty terrified bunch.

Afraid of putting ourselves out there. Afraid we won’t be liked. Afraid of playing big. Afraid we’ll end up living in a box under a bridge.

In my opinion, the number one skill set of a creative entrepreneur is not that of one’s professional expertise or marketing, it’s knowing how to manage and work with your fears.

Because fear shows up. A lot.

And yet we remain optimists. I guess we have to. You couldn’t do this crazy thing we call self-employment every day unless somewhere inside you were relatively confident it was all going to work out – one way or another.

Which turns out to leave big areas of our businesses ignored and vulnerable.

Please allow me to illustrate.

On the fear side, for example, a dwindling bank account will force you to get over any discomfort with marketing.

On the optimism side, your passion and vision for your work will compel you to create and publish (despite your fears).

But in the middle, the two amplify one another.

Optimism blocks you from acknowledging what could go wrong, while Fear interferes with you taking action.

And the stuff I think most often falls in the middle? Financial stuff, legal stuff and technology stuff.

Making money: awesome!
Not making money: sucktastic!
Looking at and understanding your money: bleargh! [sound of quickly retreating footsteps...]

Successful projects: wahoo!
Feeling like you’ve partnered with the client from hell: nightmare!
Agreements that ensure clear communication and expectations: ack! [lalalalala - I can't hear you...]

The latest gizmo, service or program: neat-o!
A completely wonky webpage: hair-pulling!
Backing up your data: too busy! later, later, later [nothing's gone wrong before...]

Generally speaking, our worries of failure and dreams of success are at least somewhat exaggerated. I don’t know of anyone who ended up living in a box under a bridge. Nor do I know anyone who became an overnight rock star.

One of the reasons managing one’s fears (and hopes) is so essential is how abstract and distorted they can be. One is always having to ground oneself in reality.

And the reality is this: while you are highly unlikely to end up living in a box (no matter what your lizard brain asserts to the contrary), there is a decent chance -

• you’ll need to show your books to the IRS
• someone will plagiarize your work
• your computer will crash or your site will be hacked

It seems to me, preventing these sorts of things from being devastating is relatively easy compared to avoiding living in a box (or just worrying about it all the time). And it’s not like they don’t have anything to do with not ending up in said box.

Yet we don’t do them. And I don’t get it.

Somehow it’s all scarier and more intimidating than the abstract fears we’re more willing to admit and talk about. Maybe because we know they are more real.

Well, there’s your resistance.

Perhaps reality is less sexy than fantasy – even when it comes to business fears – but it’s not like there’s a lack of potential drama here. Or safe environments in which to work on this stuff. Or useful tools. Or compassionate experts to help you.

If you’re serious about the stability and security of your business…
If you want your optimism to be well-founded…
If you just want less to worry about, less fear to manage…

… don’t let the stuff in the middle fall through the cracks.

• • • • •

You can work on your technology stuff this Thursday – in a safe environment, with a compassionate expert. Join me and technology-to-english translator Wendy Cholbi for a special Bite the Candy workshop: Backups & Upgrades Without Tears.

And if you want to explore legal or financial stuff, check out past workshops with creativity lawyer Rebecca Prien and heart-based bookkeeper Jessica Reagan Salzman.

• • • • •

Today this blog is two years old.

While much of what I wrote in 2008 now embarrasses me (even though I know this is true for every blogger), I still like my first-ever post a lot.

As metaphors go, this describes action in the face of risk quite nicely (if I do say so myself). And I’m proud of that person-I-was two years ago for beginning. It’s been a swell ride so far.

If you’re feeling that urge to break through and start something too – just begin. Chances are, it’s time.

• • • • •

The first small, green shoots of the flower bulbs I planted last fall are beginning to break through the soil. “No! Stop! Wait!” I want to tell them, “It’s too soon! There might be another frost!”

But they know what they are doing. They know it’s time.

Inspired by their confident intuition, I too begin.

• • • • •

Let me for once in my life feel how much I have been to blame. I am not afraid of being overpowered by the impression. It will pass away soon enough.” -Jane Austen, Pride & Prejudice

Jane Austen really does give Mr. Bennet the best dialogue. For him she reserves her most dry yet spot-on observations of human nature.

Not least of which is our tendency to forget what we’ve been shown.

My arms hurt. A lot. I thought I had learned how to pace myself so I could a) heal and b) not re-injure myself. Apparently, I have more to learn. Apparently coloring after golfing is a Bad Idea. Apparently, this is a two steps forward, one step back sort of process.

I wish learning was more straightforward. Which reminds me of something Anne Lamott once said.

After describing her son Sam learning to sleep in his new bedroom after a move to a new larger house – which was much farther from Anne’s room than before – as many nights of moving a few feet farther from her bed until he bravely succeeds in sleeping in his own room, she says,

That’s me, trying to make any progress at all with family, work, relationships, self-image: skooch, skooch, skooch, stall, skooch, stall, catastrophic reversal, bog, bog, skooch. I wish grace and healing were more abracadabra kinds of things. Also, that delicate silver bells would ring to announce grace’s arrival. But no, it’s clog and slog and skooch, on the floor, in silence, in the dark.”

And after Anne’s voice comes Havi’s voice kindly reminding me: Again is the stuck talking. So is: I always do this. It’s never the same way twice. You’re not the same person. You’ve learned stuff that makes this time different…

One of my students recently worried if all she had learned would stick, or if she would fall back into her old way of doing things.  I suppose it’s possible, I replied, but not likely. I think you like the new ways of doing things too much to go back. I find you can’t really put the genie back in the bottle.

Your genie = your genius (from the Latin for tutelary spirit or natural inclinations). Once it’s out, it’s out and there’s no going back. You can’t un-know something even if you wanted to. And you won’t want to.

I miss the clarity I had back in May. I’ve lost sight of it and it’s something I don’t want to forget.

I knew exactly what I needed to do. And I began doing it. I started to make the necessary changes – and it helped. In fact, I was super-thrilled I didn’t need to do everything on my list to see a difference. Maybe this wasn’t going to be so difficult after all! Woohoo!

Oops. Maybe not. Because here I am again.

Except not again. Because I have way more information than I did before about what helps – not least of which is the simple knowledge that I can heal under the right circumstances.

The question isn’t so much why am I here again?, but what do I need to know or do so the next time around the spiral is even more different? (because there will inevitably be more stalls and reversals).

Lesson Learned: I didn’t need to make the radical changes I was worried I needed to make. But I did need to follow through more consistently on more of the small ones.

I didn’t change enough long enough. As in permanently. I’m still talking as though this is all temporary. And there’s the disconnect. That’ why I’m here “again.” That’s what I need to know to make a lasting difference.

So… here we go. Cairene Heals Her Arms: Take 2.

I love the liberating magic of the Do-Over.

• • • • •

“Following through more consistently on making small changes” is all about me tweaking my systems in ways that make it easy for me to do the right thing and creating paths of least resistance for myself so the right things happen almost automatically. If your systems could use similar adjustments, please join me this fall (early bird ends Thursday).

• • • • •

I know, I know. Crisp air and crunchy leaves and pumpkins and hot chocolate are months away. It’s still all about home-grown tomatoes and sand between the toes and long days right now. And that’s as it should be. I’m not rushing you or anything.

I’m just feeling inspired by the very smart Laurie Foley of Intuitioneereing who tweeted this yesterday (she’s intuitioneer on Twitter):

OK, I’m declaring it here and now – by Thanksgiving, my office and my home will be clutter free. I intend to be extra thankful for space.”

That got me to thinking about what I want to be extra thankful for three months from now.

• mastering the secrets of automagicness?
• feeling comfortable in a healthier body?
• being adept at unplugging?
• connection? prosperity?
  

You can accomplish a lot in three months if you set your mind to it. There’s all kinds of space you can create for yourself between now and our annual day of gratitude. What do you want to be thankful for?

• • • • •

You could be grateful for a positive relationship with time or your spiffy manual of brilliant systems. All you have to do is join in (note: early bird prices end soon!).

• • • • •

Why do they call it a deadline when you feel more alive when you are finished?

You might be tired, but you are alive.
And probably also relieved.
Or excited.
Or satisfied.
Or inspired.
Or grateful.

I mean, the threat of death seems downright silly since that’s the least likely thing to happen – even if you don’t meet the so-called deadline.

Then you might be disappointed.
Or frustrated.
Or anxious.
Or discouraged.
Or embarrassed.
But you are still alive.

What would happen if you gave your deadlines a different name?

What if they were your alivelines?
Or proudlines?
Or woohoolines?

More suggestions?

• • • • •

You can thank the very smart Kelly for this post. It was her question that got me thinking about this.

• • • • •

A favorite piece of wedding planning advice is this: don’t worry too much about things not going according to plan. Unless it’s big and obvious, we’re not going to notice. Those of us watching won’t know the difference because we don’t know the plan.

Lately I’ve been thinking about how that applies to business and creative work. How the habit of putting something out into the world with explanation and apology is another form of perfectionism.

Here. I hope you like it. It it was supposed to be blue. Sorry.”

Which is just too much information.  Unless the thing is actually about the creative process, I’m not convinced that sharing all the choices that were rejected (for whatever reasons) is all that helpful to the recipients.

Now your disappointment is their doubt.

Why burden them with that?
Now it’s not just about receiving a gift from you, they have to respond to your sense of shortcoming.

Why weigh yourself down with that?
Now it’s not just about sharing your gifts, you have to cope with your sense of shame and guilt they are insufficient.

Makes me tired just to think about it.

So it’s not blue. That’s probably okay. (The next one can be blue. That there is more to do is a good thing.)

It’s enough. You are enough. I am enough. It’s all good enough.

I am practicing remembering that. Every day.
I am practicing not being so very attached to my plans.
And I am practicing sharing what I do without telling such an apologetic story.

It feels like bravado. There is an element of fake-it-til-you-make-it. But I know that’s temporary. It’s just the ordinary discomfort of learning something new. And it’s important that I keep at it.

Because we choose our stories about ourselves. They have a big influence on us and those around us, so it’s important to choose wisely.

In my quest for inbox zero yesterday, I was inspired to unsubscribe from a bunch of stuff I had subscribed to.  I had reached my limit. There was just too much information coming in with too many choices to make. Read this. Do this. Listen to this. Sign up for this. Augh!

So some of it had to go.

I’m always amused by how much doubt and ick can come up when doing this. What was odious a moment before suddenly becomes a personal rejection or failure to seize important opportunities or knowledge. And then I laugh remembering I can always sign up again, screw up my courage and leave already. (For crying out loud, it’s just a mailing list!)

It felt good. So good I got a little caught up in the purging. What a relief!

It was so good I was reminded why I do this sort of thing regularly and why it’s my #1 Rule of email management (there’s more – if you’re curious you can get the free guide here).

It’s one small yet really useful way to practice saying no.

In the same way folding the laundry can be a way to practice finishing, this little act of simplification can be a way for me to practice working through those moments of doubt and ick that make saying no to the big stuff a bit easier. And I get a cleaner, roomier inbox in the process. Fantastic.

It’s a small but important part of taking responsibility for my overwhelm, building my choosing muscles, and knowing just how much is enough.

• • • • •

A couple weeks ago, I mentioned how much I liked the brilliant advice of “do the half right thing.”

As I practice making every click count and finishing stuff, I’m further embracing the notion that it doesn’t have to be all or nothing.

This is one of those tired old ideas from my now useless rulebook:

> If you’re going to do it, do it right. [aka: Don't do a half-assed job.]

What’s “right”? What’s half-way?
How much is enough?
Isn’t something better than nothing?

• Isn’t a half-emptied inbox better than an overflowing one?
• Isn’t a note saying “I got your message, I’ll reply with a complete answer Wednesday” better than ignoring it until Wednesday?
• Isn’t a draft outline better than a blank page?
• Isn’t making do with the tools you have better than waiting until you have better tools in place?

How often do we let “doing it right” keep us from doing things at all?
How often does that keep us stuck in one place?

How often does “doing it right” keep us from doing the right thing? (or at least the half-right thing).

Because it’s not just about business. It’s about relationships and lifestyle and the environment – all the elements of our lives.

I first began thinking about this after a conversation with a family member about using cloth diapers. She had scored an ample supply cheaply from Craig’s List from parents who had … given up. Apparently (I don’t have kids, so I’m taking her word for it), the tricky part of cloth diapers is night-time use. So she just uses them during the day. It still helps. It helps the planet. It helps her wallet. It helps her children. She really felt those other parents were missing out – just because they felt it had to be all or nothing to be useful, that it didn’t count if they didn’t conform to an ideal.

I don’t always remember to bring my own bags when I go to the grocery store. But the times I do make a real difference.

Yes, I had intended to give that special someone a present for her birthday, but I didn’t let running out of time to buy or make one stop me from at least sending a card.

And right now, because I have to work in small chunks of time with short breaks in-between, I’m making peace with the fact that a swept-but-not-mopped kitchen floor is better than a so-dirty-stuff-sticks-to-your-bare-feet one.

And that offers me two useful opportunities: it’s a way to practice finishing something in more than one go – and – it’s a way to redefine how much is enough and call it finished (for now anyway) without also redefining myself as a horrible slacker of a human being who has no standards at all.

Both finishing and doing it right are a heap easier when we question and release some of the ideals we carry about in our heads and measure ourselves by.

So let’s all get out there and, ahem, do some half-assed work today.

That thing you don’t want to do?

I don’t mean the low-priority stuff you’ve been putting off because it doesn’t matter all that much, but that important Thing you really need to do now that makes you a little sick to your stomach when you think about having to do it? That thing that keeps staring at you from your to-do list while everything around it keeps getting crossed off?

You probably want to do 90% of it. You could easily scoot right through it if you could just get past the 10% that’s giving you a case of the icks.

So how do you do that?

Here’s what my 10% is usually made up of and how I deal with it.

#1 – I don’t know what to do.

I don’t mean that I lack a necessary bit of knowledge or a skill set.  I don’t know what to do in the sense that I’m very conflicted about the Thing and can’t reach a decision about how to go about doing it. Which explains the emotional gross out and brings us to #2.

#2 – I don’t like what I think this Thing says about me.

I’ve allowed myself to be judged by a task on my to-do list. Perfectly normal. Common. Happens all the time.  But seriously not helpful in the productivity department.

If I’m thinking, “This thing wouldn’t even be on my to-do list if I hadn’t screwed that other thing up three weeks ago,” it’s gonna be really tricky to figure out how to do the Thing until I make some peace with why I think it needs doing.

So here’s what I do to make my peace:

Step 1: What is this Thing saying about me?

I listen to what this Thing and my crazy brain hamster are gossiping about behind my mental back as they go round and round and round together on the wheel of my mind. I pay attention to what they are really saying, I bring it from the background to the foreground – even though I don’t really want to hear it. I listen until it’s clear enough that I can put it into a sentence.

Step 2: Is it true?

I then look at that sentence and ask myself it if is really true. (I like the The Work for this.) Like most gossip, it’s probably completely untrue, or at worst only partially true. So I ask myself how this vicious rumor that I’m a total screw-up (or whatever) got started anyway. And then I tell my side of the story. I issue a press release correcting my mental tabloids.

Step 3: Work from this “new” truth.

Working from that press release, I then decide how I want to do the Thing. Step 2 usually generates enough clarity for me to be able to set aside enough ick to get the Thing done. If it doesn’t eliminate the ick, at least it’s taken the 10% down to 2%. Which I can handle.

And it often also conveniently results in the task turning out better than it would have if I had just pushed through still feeling the full force of the ick. Which is a nice bit of further evidence that I really can do a thing properly and allows me to check off that to-do with gusto and satisfaction.

Thing done and pride in thing done. Win-win. Yay.

In last Wednesday’s post I mentioned there are a number of lessons I’m taking away from the recent weirdness. It was too much for one entry, but I think the leftovers are pretty tasty, so I’m sharing them in follow-up.

Here’s another morsel.

Just when you think you’ve figured out what to say no to… temptation strikes.

It used to be fear.

It was fear that would make me say yes to something I didn’t really want to do.

Fear of what the person asking might think of me if I said no.
Fear that I’d have no other way to earn the money.

Sometimes it’s still fear.

Occasionally, I still say yes to the easy, familiar thing instead of the scary unknown parts of biggification.

Sometimes it’s still about money.

But sometimes it’s boredom.

Sometimes I say yes to the sexy new thing to avoid the difficult (sometimes tedious) work of biggification.

And this is making it trickier than it used to be to tell the difference between a no and a yes.

Now, what is really a yes is masquerading as draining and unpleasant work, and what feels like an exciting yes is actually a total distraction.

** Good grief, it’s like being married. **

The choice between yes and no now comes down to short term gratification vs. overall awesomeness of the long haul.

Now it’s about truly committing to my business. For better or for worse.