I just finished The Power of Habit: Why We Do What We Do in Life and Business, which talks about identifying and improving habits. (You can’t really “break” habits; the best you can do is replace the routine withe something else. The key is identifying the cue (what triggers the habit autopilot) and the reward (what you get out of it) — both of which can be tricky to pin down — and then finding some other routine that will satisfy that reward.)

The book walks through personal examples (why does the author eat a cookie every day at 3pm and can he change his behavior?), organizational examples (can Starbucks employees all learn to have an automatic, pleasant reaction to an irate customer?), and marketing examples (why do always buy the same brands, even if we don’t like them?).

This morning, I spoke to a group of owners of tire stores. One asked what tire dealer I frequented and I said that I didn’t go to a tire dealer. I always go to the Volvo dealership for maintenance (even for non-warranty items). And as I was speaking those words, I realized why. Volvo has three years of free maintenance, including oil changes. The whole time I was thinking how nice and convenient Volvo made everything for me, they were really ingraining a habit that would last longer after the free maintenance expired.

We talk a lot about viral components and stickiness, active users and differentiators. But if we want users to come back to our products again and again, we need to both provide a reward (the awesome thing our product does for them) and a cue (what triggers the automatic action to come back). The reward alone (having an awesome product) isn’t enough.

For some products, everyone’s trigger might be different. (I never log in to Facebook unless I’m waiting for a flight to take off and everything’s packed away except my phone and a magazine, and then I always check Facebook). Some companies are trying to create new triggers rather than rely on existing ones (the big red Google+ number that shows up at the top of all logged in Google pages comes to mind).

We experience these triggers all the time — every time our phone buzzes, which is always, we look down to see what’s going on. If we have a product, can we create cues that trigger habits? And more importantly, as  consumers, can we identify cues before a habit is formed or change the routine to something else if it’s too late for that? Maybe every time my phone buzzes, I pet a puppy rather than look down to see the latest check in? Does anyone have a spare puppy I can attach to my phone?

Seattle Startup Weekend Women’s Edition is this weekend and I’m a coach. But hey, where’s the men’s edition? Can’t women attend the regular startup weekends? Is this discrimination or what?

Our Network is Based On Who We Know (And Who Our Network Knows)

We talk a lot about ratios. That tech conference you just went to had 35 male speakers and 2 women speakers. That startup you just read about has only one woman employee. And she’s the admin. We talk about all kinds of reasons for this (women don’t pitch to speak; we don’t encourage women to take science and match classes in seventh grade; women tend to interrupt their careers to have babies….) but one obvious fact is that we only know who we know.

Finding good speakers and good employees and good friends and good people for anything is a lot about first, the hard work of finding them and next, the hard work of figuring out if they’re the right fit. But even when we cast a wide net with the best of intentions, we tend to start with our network. The people we know and trust. And often, we just so happen to hang out a lot with people who are the same gender as we are. So that’s who we know. And that’s who they know. And if conferences and startups and engineering departments have a high ratio of men, it’s likely they mostly know more men. So it’s just reality that searches often start with networks comprised largely of men.

Last year, I realized I had twelve or so people working for me in either permanent or contract roles and only two of them were men. One of which was the admin. Were I a male founder with nearly all male employees, someone might have cried foul,  but the truth was that my staffing selections were not on purpose. I didn’t set out to find women to work for me and I didn’t seek out a female attorney or CFO consultant, but that’s just how things ended up. Why? Because while I have a strong network of both men and women, I just happen to have more women friends. And they happen to have more women friends. So when I ask around for recommendations, I end up largely with a pool of women candidates.

Helping women at an event like this startup weekend get more comfortable (see the third point for more on this) being involved with more events is one step in connecting the dots so a mostly male network and a mostly female network can become a larger connected network. Like me, many of the participants and mentors and judges at this event likely are connected to both men and women, and this event helps get women just starting out on everyone’s radar. Which in turn helps everyone because when you’re looking for a diverse group of speakers or employees or friends, that hard work of finding them gets a bit easier when you have networks of both men and women to reach out to.

Even Without Discrimination, There Can Be Unconscious Bias

Remember those old gender discrimination exercises where you had to tell a story about a doctor and a nurse and the point was to show that most people called the doctor “he” and the nurse “she”? I don’t know if that still happens but I know that we (as an American tech culture) mostly think we’re beyond that. I don’t want to spend too much time telling stories that refute that perception since the very definition of unconscious means that you don’t see it even if it’s right in front you, so I’ll just share this one story.

Last week, I had a mobile detailing service out to my house to wash my car. I was talking to the very nice guy who was managing the effort about his plans to start his own small business and he was asking for my advice and I can promise you that he respected my opinions and didn’t value them any less because I’m a woman.

And yet. At one point he said to me “I couldn’t help but notice you’re not wearing a ring.” And then he explained why he was asking. He motioned at my house and said (after asking for my advice as a business owner remember), “I was just wondering, where is the man who is paying for all of this?”

You Feel More Confident When You Feel Less Alone

Without question, effective networking can give a boost to someone who wants to be be successful in today’s startup culture (whether as a founder or an employee). And it can be scary for everyone (both men and women) to go to an event such as a startup weekend for the first time — not knowing what to expect, not knowing anyone. But it can be even harder when you feel completely different from everyone else. A couple of weeks ago, an employee of mine was talking to me about a Rails Camp he was going to that weekend. He kept using male nouns and pronouns to refer to the group that would be there. Finally, I interrupted him. “You mean the men and women…” Well no, he told me. Only guys have signed up.

A few years ago when I still worked at Google, I was at a luncheon at the Grace Hopper conference for the women that Google had sponsored to attend. I was talking to one college student who told me how grateful she was for the opportunity to be there because the entire time she’d been at college, she’d never had another woman in her computer science class. She’d never had the opportunity to collaborate with a woman. Ever.

I’m not saying that women can’t hack it in environments with a lot of men, I’m just saying it’s nice sometimes to be reminded that other women are out there. I don’t want to get into stereotypes about how men and women are different, but I think it’s telling that I’ve been avoiding telling the following story in this post, even though I’m a confident, successful woman in tech, I have large networks of both men and women, and I don’t really care if you know that I went shoe shopping last weekend.

Years and years ago (I mean it — this was like 1995 in the telecom corridor of Dallas) I started a new job at a startup that made testing equipment for SS7 networks. On my first day, a woman rushed up to me. “I”m so glad another woman finally works here. Finally, I have someone to get manicures with!”

I resisted telling that story because I didn’t want this post to about women getting manicures, but you know what? In part, that’s exactly what this post is about. At the end of a hard work day, a woman can’t always turn to a male coworker and ask him if he wants to go grab a drink and talk through things. In some situations, of course. But in many others, I’m sorry, but she just can’t. And we all need people we can turn to.

If this event helps a few more people find someone they can turn to, I’m all for it.

A popular new year’s resolution among those of us in the tech world seems to be focused on getting out from under being so overwhelmed. We’re drowning in a sea of information, our to do lists, our email, travel, work. We buy time management software, read books on getting things done, install plugins for our email, and yet we still can’t seem to be free of the ever present feeling of doom: of being behind, leaving things undone, of running and running and not getting anywhere.

How did we get this way? Especially as many of us in this predicament presumably have substantial control over our workloads. We’re entrepreneurs, tech journalists, consultants. The things that threaten to crush us are too many flights, too many speaking engagements and conferences, too many articles to write, too many projects to complete, too many open tabs, too many blog posts to finish.

And by “we”, of course, I mean me. How did I get this way? Several years ago, when I was still working at Google, I talked to a life coach (yes, Google has those too, along with the chefs and masseuses) about my lack of work/life balance. How do I get better time management skills, I lamented. He told me I didn’t need better time management skills. Instead I needed to cut my to do list in half. “You’re trying to do too many things” was his assessment.

The Luxury of Taking On Less

A simple problem to fix: take on less. Simple, but perhaps not easy.

Consider: we are doing too much. We feel crushed by the weight of our obligations. Yet we tend to be the ones who sign ourselves up. That reads like a contradiction, but the reality is we see the items on our to do lists as obligations, not choices. It’s not enough to decide to take on less if the reason we’re taking it all on in the first place is we feel that we have to. There’s all kinds of advice about how to say no to things, but learning how to say no doesn’t help for things we think we have to say yes to.

The next question then is this: why do we feel we have to take these things on? Surely the answers are as varied as we are, but one potentially core reason struck me as I was reading this post by Bryce Roberts about choosing to say yes to fewer things:

“If I’m not totally excited about something- an new investment, working with a new person, attending or speaking at an event or getting involved in a new project- I’m saying no.”

The ability to do that — to say no to things you’re not super excited about — that’s a luxury. Most of us who have that luxury now haven’t always had it. In fact, many of us who now have that luxury likely only have it because of our tendency to do just the opposite — not only say yes to everything but to seek out new things to say yes to.

Saying Yes To Everything Leads to Success

I get lots of variations on this question: how did you end up with such a weird career path? And the real answer is that I not only sought out opportunity beyond my job description, but I created opportunity and then voluntarily (wholeheartedly and excitedly) worked extra hours for no pay.

For instance, when I was 19 and in college, I worked as a cashier at a home improvement warehouse (similar to Home Depot or Lowe’s) for $5 an hour. Some of the bulkier items, such as lumber and metal pipes, had a tendency to lose their bar codes, so the registers had big binders full of descriptions and SKUs. However, this being a hardware store, the pages were dirty and covered with paint, lists were jumbled together in no order at all, and it was nearly impossible to find the right code. The best you could do was hunt for the right general topic area and narrow down your search until the customer became agitated and impatient and then scan the picture that resembled most what was in the cart.

As it happened, through the magic combination of a college bookstore that let me charge things to my student account, Apple’s educational discount program, and the ability to pay my account with student loans, I had recently procured a PowerBook 140 (cutting edge in early 1992). I took one of those binders, a notebook, and a pen, and walked the store to get missing SKUs from the aisle signs. I compiled everything into an organized structure in PageMaker, printed it all out, laminated the pages, and put new binders at each cashier station.

How much did I get paid for this project? Nothing. I did it all while I was off the clock. Who asked me to do this? No one. What did I gain from it? When I applied for (and got) a writing job at the corporate office of the same company after I graduated, I was able to claim experience not just with cashiering, but with PageMaker and store operational process (as you might imagine, that wasn’t the only such project I took on). Before graduating, I quickly moved up through the ranks at the store, eventually ending up working for the general manager in a position I basically designed myself, doing whatever needed to be done, in whatever hours I had available (which helped me juggle working full time while taking a full schedule of classes).

The point is that these ways of approaching the world (taking on whatever comes our way, seeing a hole that our skills can fill and bridging that gap without even being asked) are in large part what has made us successful.  It’s the best way we know to navigate the world.

Presumably, then, if we stop operating in these successful patterns, we become unsuccessful.

And this, I think, is the core of where we go wrong.

New Situations Mean New Ways of Achieving Success

We are reacting to new situations in the same old ways, not realizing we aren’t in the same old situations. And maybe these new situations aren’t best served by capably taking on everything that comes our way. Instead, we perhaps need to learn new patterns: providing an environment where others can shine by delegating well and providing support, pausing to evaluate the more strategic path rather than the reactionary one, providing better service, leadership, articles, talks by saying no to the speaking opportunity the day before so that we get a good night’s sleep rather than take the red eye across the country.

A key, perhaps, to not being so overwhelmed is to realize that saying yes to everything was the right response then, but it’s not the right response now. It’s not learning how to say no, but learning that in fact, saying no is not only a choice, but a good one. A successful pattern of its own.

Sometimes working really hard isn’t enough. Sometimes it’s even the wrong thing to move you forward. I was thinking about this the other day, not as I was running my company and pondering being the “duct tape” of my organization vs. the leader who creates a sustainable business framework, but as I was attempting to steer a three person kayak in Elliott Bay.

My sister was in the front of the kayak and my seven year old niece was in the middle. The kayak purveyor had kindly given my niece a paddle. My sister, not an experienced kayaker, but a very nice and lovely person, would become alarmed that we were heading too close to a pier or the shore or a boat and would frantically paddle in an attempt to move the kayak in another direction. Meanwhile, I would press one foot a few inches on a pedal that controlled the rudder, and the kayak would drift into the right direction. My sister would breathe a sigh of relief.

My niece jumped right in to help: paddling backwards, her paddle kicking up lots of water at me, generally having a great time. These efforts, while vast, did not actually propel the kayak where we needed to go.

What propelled us was the rudder. And more directly, my foot pressed a few inches on a pedal.

We’ve all scoffed at the ridiculous “work smarter, not harder” motivational posters because sometimes, there’s work to be done and you just have to roll up your sleeves and do it. But sometimes, you just need to make sure you’ve got the pedal hooked up to the rudder.

Casey and Sofia On Our Great Kayaking Adventure

This is not a post about Heidi Montag and Spencer Pratt. I mean, it sort of is, except that I don’t actually know who they are and haven’t ever seen them except on magazine covers in the grocery store.

This is a post about running a sustainable business. No, really.

When I started my company, I knew nearly nothing about running one. And it turns out, there’s quite a bit to running a company beyond knowing a lot about whatever it is you’re focused on building. I’ve learned the differences between an S-Corp and a C-Corp, what NNN and TI mean, what E&O stands for, and that Seattle’s revenue-based business taxes are, well, kind of a bummer.

I’m still learning. A lot.

One thing I’ve learned is that it’s not enough to provide something that people want enough to pay you for. How you manage cash flow and expenses is at least as important. You have to think carefully about the ROI of every expense. How will the company benefit? Is this something the company needs right now or will waiting a bit be just as beneficial? You have to balance the need to make the right investments and have the right resources with the need to not drain the bank account dry with lots of random expenses you hope will pay off down the line.

You worry not only about spending money, but about not spending money. What if that one expense is what makes all the difference to move the company forward?

Which brings me to Heidi Montag and Spencer Pratt (apparently known colloquially as “Speidi” by their closest, er, fans). I came across a fairly fascinating article on the Daily Beast about the rise and fall of their fame. Despite being on the covers of all of those magazines in the grocery store, they are now, according to this article, broke and living in Spencer’s parents’ beach house (a pretty good state of being broke, I guess, if you can get it).

Where did all the money go, the interviewer wanted to know.

Here’s what’s interesting. The money flowed out as soon as it came in (from appearances and the like), but not because they were partying it up, renting private jets to take them to Paris for dinner, throwing hundred dollar bills out open windows just to watch them flutter in the breeze. No, they spent the money on crazy props (plastic surgery, mystical crystals, a monster truck)  that they thought were investments in their careers.  They believed these expenses were necessary in order to sustain their fame. Without all of this spending, they thought, the fame would dry up and so would the money.

Only the fame dried up anyway. The article goes into why that might be and how reality star fame perhaps is different from fame based on true accomplishment of some kind, but I’m more interested in the money. As the article notes:

 “I thought I was investing in myself and my brand. Like Kim.” As in Kardashian, who came up often during the interview. Heidi continued: “When she buys these clothes, she’s investing in herself. Because she is a big brand and is likeable. I thought I had that potential.

How do you know if you’re investing in something that has potential or throwing away your money completely? Or, as is the more likely and more painful situation for entrepreneurs, spending on the wrong things or at the wrong times?

Doug Edwards’ new book I’m Feeling Lucky: the Confessions of Google Employee Number 59 has a section about Sergey and Larry’s guiding principles in the early days of Google. Efficiency. Frugality. Integrity. Doug recounts a story of an early business trip with Sergey to Italy.

“That seems kind of expensive,” Sergey said, looking at the hundred-dollar price for a cab from Malpensa airport to downtown in Milan in January 2003… “Maybe we should take the bus. It’s less than five Euros a person.” The bus? What? Were we college kids backpacking on spring break? Maybe we could just hitchhike into town. We compromised on the train, which ended up saving us fifty dollars.

It’s somewhat amazing that Larry and Sergey, with no experience running a company, and who brought tech, not business skills to the table, were thinking about things like keeping travel expenses low. And no doubt thinking about all of those details around sustaining a business contributed to their early success.

For the record, I would have paid for the cab. But probably not bought the monster truck.