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.

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 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.

I’m conflicted.

On the one hand, surely Penelope is being purposely controversial. How is a person like me or like Tara supposed to react to blanket statements like “women don’t want to run startups because they’d rather have children” and “if you want to know why you shouldn’t do a startup with women (if you’re a man), read on.”

These statements are absurd.

And yet as much as I want to entirely discount Penelope Trunk and what she has to say, deep down, underneath all of the ridiculous hyberbole, sweeping stereotypes, and flat-out offensive, clueless wrongness, I think she’s trying to say something important and true about what it takes to start a company from nothing.

She’s wrong in her conclusions. She’s likely right in how the truth of what’s hard about startups applies to her (that she wanted to have children, that she had trouble in a coed co-founding environment), but as Tara quoted @LusciousPear, “The plural of anecdote is not data.”

What she may not realize she’s actually uncovering is how hard it is to be an entrepreneur (not a woman entrepreneur, not an entrepreneur with children, but any person who has the crazy notion of starting a company). When she writes  ”there is no woman running a startup with young kids, who, behind closed doors, would recommend this life to anyone,” what she may not understand is that there may not be anyone running a start up AT ALL would recommend this life to anyone.

A few weeks ago, someone was interviewing me and asked me about being a role model to younger women. I felt a moment of panic. Do I really want to encourage a young woman (or anyone, really) to work twenty hour days, to work on Christmas, to be almost happy when her cell phone breaks because then she can focus for a few hours on reducing her inbox?

Penelope’s post about running out of money right before Christmas and not being able to make payroll isn’t an exceptional situation that only she has experienced. You can’t stop and rest if you’re sick (or struck blind as she writes about) or you’re tired or it’s your birthday. Yes, it’s not always like that, and yes, bootstrapping makes it all even tougher. But when the company rests on you, you’re the one who has to make sure it all holds together.

James Altucher wrote 100 rules for being an entrepreneur that include:

• It’s not fun. Keep sharp objects and pills away during your worst moments. And you will have them.
• You have no more free time.

But he also says:

• Sleep. Don’t buy into the 20 hours a day entrepreneur myth. You need to sleep 8 hours a day to have a focused mind.
• Don’t kill yourself. It’s not worth it.

Someone asked in the comments how those two sets of things could possibly go together and he answered, “It’s not easy or everyone would be rich.” Someone asked how to get sleep when they were so stressed out and he suggested medication.

This situation isn’t unique to entrepreneurs. In Tough Calls From the Corner Office: Top Business Leaders Reveal Their Career-Defining Moments, the author writes:

“There is one more common thread that runs through the stories in this book… All of [the executives] knew they were in for a lot of grueling work and long hours.”

When I read How Remarkable Woman Lead: The Breakthrough Model for Work and Life (which is an excellent book, and not just for women), I kept looking for the secret to work/life balance (even though I already knew it didn’t exist), and instead the book uncovered that women who managed the chaos didn’t find time to relax and take breaks, they instead identified what energized them so they could keep going.

One of the women profiled in the book, Gerry Laybourne, founder of Oxygen Networks, said “there were times I couldn’t breathe. There were times I felt exhausted. There were times I couldn’t imagine how I was going to put one foot in front of the other.”

The book notes that some women recharge by declaring flights a work-free zone and a time to relax. That’s when you can vacation? When you’re on a flight from one meeting to another?

A couple of weeks ago, I was filling out a questionnaire for being one of the Puget Sound Business Journal’s 40 Under 40 for 2011 and got to the question about what I did for fun, to relax, in my free time. The truth? I find things that make me happy that I  can do while I continue to work! I can eat ice cream and keep working! I can wear comfortable slippers and keep working! (And now, if you read my answer to that question in print somewhere based on what I wrote on the questionnaire, only you will know that I lied when I talked about beaches and summer reading.)

So, no, likely not many of us really recommend that kind of life.

(Penelope was, I think, trying to make a point about how startups are hard so why introduce friction (friction in this case being a diverse team). There’s a point to made there as well, although again, I don’t think it has anything to do with gender, but that’s a post for another day.)

Through coincidence of another tweet by Karen Wickre, I was led to a post by Nilofer Merchant, who linked to yet another post about shutting down her business of 11 years. She may have gotten to the heart of a real solution.

“In essence, I was a “doing” entrepreneur saying “I’ll be your duct tape”. Which works fine for a while. Then, if you are “successful” as I turned out to be, my little “duct tape” couldn’t hold strong when it was the plug for a big damn of revenues, delivery and projects. Being a “doing-Entrepreneur” is not enough to scale a firm to success.”

So what, then?

She says:

“Entrepreneurs: working hard is never enough; our goal to create a sustainable enterprise. Sustainable doesn’t mean “I will work myself into the ground and hope someone can give me a $1M at the end and then they can grow the firm to the next level”. Sustainable is more like the thing that lets Ev Williams hire Dick Costolo at Twitter and then divide roles so the different fronts are well covered. I would bet the Corporate Board at Twitter were thinking about sustainability so they didn’t lose their talent but found a way for a thriving enterprise.

By being the best “doer” for your business, you’re not necessarily being the best “leader” for your business. And as far as I’m concerned, that’s the more important role — be the visionary talented leader that creates value in a business. In other words, be a great entrepreneur. Master your own priorities so you can sustain a business well.”

The way that happens for every business, for every entrepreneur, is different. But I know that it can, and does happen. Advice is welcome. From men and women.

I’m a entrepreneur in Seattle.  I’ve been running a profitable, boot-strapped startup for over three years. I’m a woman in technology. I’ve been building web sites since 1995. I’ve worked for huge corporations, tiny companies, and everything in between. I’ve been the most junior person at a company and now I’m a CEO. I’ve built software. Managed developers. Been an advisor for other startups. Performed due diligence for venture capital firms and have been the one asking the tough questions at VC pitch meetings. I travel a lot. In the last year, I’ve been to six continents. I do a lot of public speaking. I love food. I wrote a book.

Maybe writing about some of these things will be helpful to someone else, and to that end, welcome to the new site. I’m relaunching my company site, ninebyblue.com, at the same time I launch this site, and the writing is going to heat up over there too.

Turns out that running a company and traveling around the world takes up a lot of time, so I’ve decided to just take my own advice and launch early and often with these sites, even though a bunch of stuff is still under construction. We’ll be fixing stuff throughout the coming days and stay tuned for a lot more!