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An Entrepreneur's Holiday Weekend: The good, the bad, the unproductive

This week I took some extended time off around the Thanksgiving holiday--two whole days! The first day of my vacation I spent catching up on email, thinking of blog post ideas, and, OK, just checking in on our company team meeting. Hey it was a goodie, not one to be missed. My husband also had the day off and couldn't really make sense of my choice of activities.

"Babe, what's the point of taking vacation if ..."

"I know, I know."

The remainder of the day I played with widget options for my soon to launch new blog, went to the dentist for a follow-up, and then baked pumpkin pie. In my true style of underestimating how long it takes to properly create things In Real Life, I forgot that one must let dough chill before rolling it out. This not so minor detail, and some general wonkiness I encountered with my dough, put me back about 2 hours. I went to bed well past midnight.

Wednesday we drove from the Bay Area to Anaheim to spend Thanksgiving with Jesse's family. We encountered pockets of heavy traffic, which irritated my husband to no end, but which I found rather convenient--it afforded me more time to catch up on trade newsletters and articles I had sent to myself to read when I'd get an extra moment. At one point, I noticed an email request from my business partner and figured, "Hey, I'm in the car, so why not just crank it out."

I worked on the laptop until my power died, then enjoyed the throngs of people stuck in gridlock for the next few hours.

Thursday I really did take the day off. We took a long bike ride on the tandem of Jesse's aunt and uncle. After lunch, I sat on the couch next to Jesse to watch the football game with his grandfather. Next thing I know, I'm waking up.

"What just happened?"

"Enjoy your nap?" Jesse said.

"That was weird. I wasn't even tired."

Both Jesse and I knew what had happened--what happens every time I have enough time off to absorb the fact that I'm on vacation--my body shut down. For the remainder of the day I felt bone tired and disoriented, like I was just waking up. Every few minutes I checked my Blackberry for email, out of a nervous habit. With the exception of a few Facebook and Twitter alerts there was nothing. Not having anything new pop into my inbox made me a tad agitated. It felt like there was something wrong. I had to remind myself that it was Thanksgiving. When we arrived at Jesse's aunt's for dinner I put my Blackberry in the glove compartment.

Friday Jesse was up with the sun. I found it much harder to wake up. I sauntered into my in-laws' kitchen and started to pick through the New York Times. I helped set up a wireless router, and then around 1 pm felt this sudden panic that I was letting the day pass me by. Jesse had mentioned that his parents wanted to see an exhibit at the contemporary art museum in La Jolla.

"When are we going to motivate?" I asked Jesse.

"I dunno. I thought I might study for my (licensure) exam for a while."

"We need a plan, Jesse! When are we going?"

"Later today."

"When later today? The sun sets at 5!" My voice became more and more urgent.

"Fine. We'll leave at 2."

At 2:15 we left for the museum. None of us were that impressed with the exhibit, but I was glad to be out and a tourist, taking in the sites on the waterfront. I was already thinking to myself, "Where are we going for dinner? Do we need reservations? When should I squeak out a blog post?" I told myself to shut up. We watched the sun set. I'd done nothing productive, and it was OK.

Saturday I squeezed in some exercise before friends arrived for brunch. I felt more energized than I had been, despite the fact that I had had a work dream that woke me up in the middle of the night and I couldn't fall back asleep for hours. It wasn't a scary or traumatic dream, just one that required a degree of thinking. I found it strange to wake up at 3 in the morning in a state I find myself in during, say, a team meeting: Fully alert and ready to report information.

We did some shopping that afternoon, or browsing, anyway; I found that I wasn't inspired by anything at the stores. Later, I tried to blog and realized I was a blank slate, no words were appearing that I considered compelling enough to write down. I thought to myself that it was a shame, really; I finally had some time to blog, and I couldn't think of a damn thing to say.

Sunday we drove back up from SoCal, and I caught up on more trade newsletters. It occured to me that there were only so many to catch up on before it made sense to let some information go. I listened to hours of CNN on satellite radio and wondered, "Did any of these people take the weekend off?" It seemed that there were many people whose jobs required them to be even more available than mine did on holiday weekends, and I felt grateful and guilty.

We got back home earlier than planned and even a bit unsure of what to do with ourselves. I had planned to start working as soon as I got home, but as a personal dare I decided to think about my long weekend--what I did, not what I didn't do. And write it down, even the seemingly mundane stuff, so that I would be more aware of how I spent my "free" time. I asked myself, how much of it did I actually spend on being free? 

The Entrepreneur's Guide to Time Management: How to Pick a Brain Properly, and How to Selectively Allow Yours to Be Picked -- Part II

Some more food for thought, following my post from last week:

• Brain Pickers: Be specific. A few months ago, a man approached me--or more accurately reproached me--about my company's attitude toward him. He had wanted to work with us, but we weren't being receptive.

 "OK," I said, "tell me more."

He did, telling me nothing that would indicate why we should work together, only that he resented that my company charged for advertising across our network. If only we let him share his product with our community in partnership, we'd see what a great fit they were with us.

After the event, I followed up with him, as I was sensitive to the fact that prior to our meeting he had felt unheard. I explained that we were approached by people asking to partner like this often, and unless there was something that would benefit us both upfront it would be hard to justify a test relationship. Did he have any ideas? Anything to make me think we should place a bet on him by changing our business model to work with him? His note back was short: He had been hoping I would have thought of something. 

This is arrogant: Assuming that others should immediately see your value to them. And it's lazy. I'm sure that many callers aren't intending to be that way when they approach with little specificity--I'm sure many think they are being accommodating by not assuming how they could work with you. But with time at such a premium, I prefer to receive a note that says: "I think we should work together because of X" and letting me counter if that reason isn't important to me, rather than saying, "I really like what you are doing, let's talk and see if there's a way to work together."

• Brain Pickees: Consider everyone a potential resource. Mahalo Founder and serial entrepreneur Jason Calacanis openly condemns VCs and angel funders who charge entrepreneurs for the opportunity to pitch their businesses, and I have to agree with him. The sources that are worth their salt--and Calacanis points to VC Fred Wilson as an example--may be tough to reach because they are busy people, but if your concept is worth something and you present yourself well, you should get a meeting, without paying for it.

I learned this waaay back when I was in print publishing: You don't pay an agent to read your manuscript. Sure, it takes some moxie getting an agent to see your work, but agents that charge you for the opportunity tend not to have the reputation required to take your work to the next level.

It may seem counter-intuitive but it's true, because successful people don't stop looking for ideas and opportunities. They don't "top out" once they reach the big time. As much as I don't always agree with Diddy's approach to talent development (as I've seen on his various Making the Band programs), I do admire his willingness to go back to the roots of what gave him success in the first place in order to mine new talent and stay fresh and relevant in the music industry. In many ways his show is an early, analog version of curated crowdsourcing that worked.

• Brain Pickers: Be useful: Back when my partners and I were contemplating seeking venture capital funding to grow our business, we sought out a number of experienced people like Guy Kawasaki, Steve Perlman and Caterina Fake to help us get some perspective on whether to do this, and if we were to, how to do it right. These are some busy, successful people, but they were only too happy to help, for many reasons. These people were very generous with their time, and we made sure we didn't waste it. We also did what we could to be useful.

You may come to the table thinking you have nothing to offer someone who is already successful, but put yourself in their shoes: Often success can  become a buffer from some of the less-desirable things about entrepreneurship (like having to do everything, even the things you're not good at) but it can also keep you a few feet removed from the ground, where you have access to information. I often complain that as our business grows, I have less time now to get the skinny on my favorite topics on blogs. Nor can I go to as many meet-ups, where even the most random small talk yields insights on my industry. I have to make an extra effort to stay connected, which a few years ago was part of my everyday world.

When we met with Guy Kawasaki, he was in transition, learning more about the blogosphere and what made it tick. I can only hope that in some exchange for his wisdom we were able to bring him closer to the the space before his new venture, popular with the women's blogging community, AllTop launched.

Before I get my brain picked, I often ask myself, "What new things can I learn from this conversation?" Before I pick a brain, I ask, what info can I bring to the table?

• Brain Pickees: Expand your horizons. This goes back to consider everyone a resource. But even while being open you might not see opportunities in places that are surprisingly fertile. A few months ago, I was approached by someone I'd met years ago to be on the advisory board of a children's entertainment and educational company he now headed. He was aware that I could not offer up free media or proprietary information; he just wanted to tap my thoughts on marketing to moms.

I don't have kids, so the free DVDs weren't what tipped me to saying yes. Rather, it seemed like an opportunity to get better at what I currently do. The beauty of the position is that it has re-enforced my connection and thought leadership in an area in which I knew a lot, but now know much more. I've gleaned new insights for my own business as a result. Now that's a win-win.

• Brain Pickers: Let people know when picking their brain has helped. And pick your moments. So this goes back to good old-fashioned upbringing and lives next to writing thank you notes in my top five things that have carried over from my mother's nagging. But having now been on the other side of the equation, and having seen how my helping someone has made a difference, I insist on doing this when I am helped. When people I help do this, I am more excited to help them again.

That said, even if you send home-baked goods to everyone who has helped you, if you ask for too much too often, you wear out the good will. People can only eat so many cupcakes. People who continually go to the well because they are thirsty will find it dry if they don't give it time to fill up naturally. For this reason I recommend that BPs pick the best use of a source's time and not waste it on things she could get without that source's help. I recall responding to a stranger's emailed request for help starting her personal blog with a few general resources for getting started. I don't do this kind of work and thought she should have researched what I do at my company before sending her request, but I appreciated her desire to get started and wanted to encourage her. When she followed up asking me to interpret some confusing information on the site I sent her to, I was much less helpful: I told her to do exactly what I did when I started a blog and needed help: Call customer support.

This example is egregious, but think of people you might have helped in the past who followed up, essentially because they did not want to do the work that you suggested. If you provide support you are enabling them to eventually fail.

The Entrepreneur's Guide to Time Management: How to Pick a Brain Properly, and How to Selectively Allow Yours to Be Picked -- Part I

Having people ask to "pick your brain" can be the ultimate compliment to an entrepreneur. It makes us feel like we're experts in something, or that we've been successful enough at something that someone values our thoughts. But brain picking comes in many shapes and colors. Some brain pickers (BPs) are just looking for inspiration; talking with you stirs their own ideas. Others want resources--money, contacts, insider knowledge that will help them with their endeavors. None of these are inherently bad, but none of them are good if you aren't getting something out of the sharing.

I used to love it when people asked to pick my brain, especially early into the business. I might not have been drawing a paycheck, but by golly! Someone wanted to talk to me about something. It was a small sign of traction.

Today it's different. I still love helping people, but I've been confronted with the limits of my time and energy. I've had to be brutal at times about how I prioritize "non-business-related" requests. And I feel badly about it, I mean what entrepreneur doesn't include in her war stories a paean or five for the big shots who threw her a bone--a contact, and introduction, or an informed opinion--her way that made all the difference. Since becoming an entrepreneur I've become more determined than ever to pay it forward.

But paying it forward can't be confused with sucking yourself dry. Even while helping others with their endeavors, I see no reason why we can't always strive for win-win situations. I hope that the following ideas stir your thinking--both brain pickers and pickees. I'll write this up in installments this week. But let's start with a few:

• Brain Pickees: It's OK to say, "Not a good time." Even if you want to help someone, sometimes you can't. I recall respected peers asking for business intros and advice when it just wasn't appropriate for me to provide it. Perhaps my company was in the midst of a negotiation with the requested company, or sharing my info would compromise others. It sounds like common sense to respectfully decline, but it really is a tough lesson to follow, especially because of the "pay it forward" thing we entrepreneurs tend to ascribe to.

• Brain Pickers: Make giving you help as easy as falling out of bed in the morning. I have a pal who is a budding, but successful, entrepreneur. She runs a women's community. "I knew that things were starting to go well when people started reaching out to me, asking me for help," she says. A doctor and artist, she's had many different career lives and experiences, so she was asked just about everything, from "Do I have H1N1?" to "How did you start a business?" At some point, the requests began to hinder her everyday work. She decided to create a filter, if you will, to separate the quickie information seekers from the serious people.

"I ask them if they will join me for a hike," she says. Some background: my friend lives in what could best be described as a remote area, near the lovely, pristine Marin coastline. She's committed to hiking an hour each day. I've joined her, and it ain't a quick jaunt or drive.

"The right people will make it out and help me kill two birds with one stone," she says.

Likewise for me. If I am approached by someone who is seeking information that is not a part of my daily business plan, they must be willing to call me in my car (as my commute hours are often the best place to reach me), or make it to my office. If you miss the time that we've agreed upon for a chat, please let me know in advance, and give me a good reason. If you miss the time, I won't be calling you to reschedule. In some cases, if the person seems to be disrespectful of my time, I won't respond to requests to reschedule.

Again, it's not about being cruel or mean, it's about saving time for the good stuff, and for the people who will use your time well.

More to come later this week.

The Secret Handshake I Still Don't Know at United Airlines

I fly a lot on business. A lot. A couple of years ago I started actively flying on United because it's a major airline at my local airport, SFO, and it flies regularly to the cities I fly to most often: New York and Chicago. And I started doing the math and realized I wasn't doing myself any favors by constantly changing my airline and finding myself booked in the back of the plan, next to the bathrooms, every time.

I'm not sure what my total miles are for this year, but as of this date I've amassed about 240,000 miles and 40 upgrade segments. This is my balance after paying 45,000 miles for a Red Carpet Club membership and spending some of my segments on upgrades. If the demand for upgrades by other frequent fliers were not a factor, I would get to upgrade to business or first class every time I fly.

This year, despite my "1K" status, which I love to throw around when I want something from United (like a guaranteed upgrade) there are some things that still elude me. Even when I book well in advance, I get upgraded to business or first class maybe 50 percent of the time. And about 40 percent of the times that I do get upgraded, it's on a plane with what I call "lame first class"--an antiquated model that only affords bennies like a slightly wider seat and no charge for a snack box (the flight attendant even pre-opens it for me, so I don't break a nail trying to get the plastic off.) Despite the claims that some flights have wireless, I have yet to experience one, and only a handful of planes have charging outlets (and of the ones that do I need to contort myself like a Cirque du Soleil performer to reach it, feeling under my seat for the two indiscriminate holes where an outlet is rumored to be.)

Needless to say I have been disappointed in my United 1K membership, despite having flown with them an estimated 40 times this year (and about 120 times over the past 3 years), including international trips that required connecting legs on partner airlines that didn't always honor my miles (or made it difficult to redeem them), dinky puddle-jumping legs from one of their hub airports, and the standard flights to New York or Chicago.

I'll say upfront I'm not always loyal to United. Our office manager won't book me on it if I'm not flying their more common routes and have to pay a small salary to stick with them. I've flown Delta to Florida, Atlanta, and Cincinnati, which saved me time and money. I've flown Southwest to LA, San Diego, Phoenix, and Las Vegas and see no reason why I should pay more for these quick jaunts. But still, I would say I qualify as a loyal United customer because I fly them most often.

So imagine my surprise today, as I'm checking into my flight from JFK to SFO, when I ask the attendant at the check in counter what my chances are of getting upgraded:

"You are fourth on the list."

"Really. Do you think my chances are good?"

"Mmm depends. You have two other 1Ks and a Global Services member ahead of you."

I've heard of "Global Services" and see that these folks get preference over 1Ks, but I've never been sure why.

I ask the attendant, "What does it take to be a Global Services member?"

"You have to be invited."

"REALLY! And what does it take to be invited?"

"I really don't know, ma'am."

I could feel the surface of the soapbox materialize under my feet. You have to be INVITED into this club? And the criteria isn't public? Naturally, I don't take this as a final answer.

"C'mon, you must really know: Do I need a certain number of miles?"

"I don't know, ma'am."

"Do you need to spend a certain amount of money?"

"Again ma'am, I don't really know."

"Do you need to be deemed important somehow?"

The attendant shrugged his shoulders, and with this gesture I backed off. I told him,

"I'm going to find out why I haven't been invited to be a Global Services member. Mark my words."

And I say to all of you. A gal who has built a business grounded in meritocracy: Mark. My. Words.

Encounters: The Aviator, or what I want to be when I learn to play

(Caption: Our view of Big Sur)

I met Kareem because we needed a contract script writer--badly. Copywriting was not Kareem's only career strength, and not exactly a career passion, but the project was temporary, and he had just come from a digital agency with too much experience on his resume to get picked up immediately in a downsizing economy.

Prior to meeting Kareem I'd spoken on the phone to another writer with an agency background. She was ready and eager to jump into our project. Shortly, after being briefed about the aggressive deadlines and requirements of the client, she reconsidered and backed away, mid-script. We were supposed to shoot the following week.

In ideal circumstances, we strive for a sane approach to project management, where we plan such things as scriptwriting and shooting schedules way in advance, but being in this Webby world we're in, projects are often inked close to launch. Some people thrive in this kind of environment, some fight it and give in begrudgingly, some reject it outright. I needed to see how Kareem would react early, before hiring him.

I was brutally frank in our interview. Our "co-created" project with Brand X was exciting stuff, but it was not without client oversight and last-minute changes. I said something that I wish I hadn't,

"I need someone who's comfortable with user-generated content that's not all user-generated...I mean, it is, but with an eye toward the brand... not that they want to influence the script, of course...it must be authentic, but brand-friendly..."

I decided to look up from staring down at Kareem's extensive resume; he remained smiling and calm.

"Yes, I think I understand," he said. He told me of several on-set projects he'd done as a creative director. The personalities he'd encountered, the seemingly contradictory directives. It was clear to me that, from a production standpoint, he'd seen it all, and he understood the dichotomous nature of client work--something that often relied on a paradoxical act of creating authentic connection. He didn't bristle when I told him we were shooting next week and still needed scripts to submit for approval. And these scripts depended on the availability of his script subjects, whom had yet to be selected, let alone contacted.

"No problem," he said.

The following week, he arrived for a briefing meeting with snacks for the team. Shortly thereafter, scripts written and approved, he arrived at the set early with props that our producer had trouble procuring. Everyone who had arrived on-set had been briefed by him and was ready to go. He got along famously with the camera crew and director. Later, when the rough cuts were complete he adeptly knew where to cut and even how to retroactively make guests look more comfortable than they actually were. Client requests that may have overwhelmed another writer/producer were creatively integrated with no complaints.

After our final shoot he suggested we go grab some coffee. Already I was trying to think of how else we could work with Kareem until a more suitable position opened up for him.

It was a hot day; I sipped ice-coffee in an air-conditioned Starbucks. He asked me, "Do you fly much?"

Option 1: Work more; Option 2: Work less; Option 3 ...

Kris at The HR Capitalist caught my attention with his post, "Being a Star - Either Put In More Hours Than Others, or Start Eliminating Stuff (But Stop Whining)...." He says:

Work/life balance is a choice.  You won't be able to be your version of Bono with work/life balance as your goal.  More and more, I run into super sharp people who are amazed at the entitlement culture of talented folks who say they want to be stars, but won't put in the time to outwork others and are outraged when told that's what it takes.

If you are not inclined to put in more hours, Kris says, "you need to start eliminating things that you don't think matter, the things you can get away with not doing, not being involved with at work."

This is the choice of anyone seeking success, but notably of the entrepreneur. As my company has grown, my time management strategy as evolved--or devolved as the case may be:

• Phase 1--The first date that won't end: You have a crush on all the excitement that your business is providing for you in life and unwittingly give it all the time that it needs. Other things need to happen, like sleep, so you just add more work hours to your day and keep plugging after dinner, or after your spouse knocks off for bed. When opportunities present themselves, you drop everything.  For instance, someone you've wanted to meet with for some time wants to connect for breakfast at 7:30 a.m. the next day in New York City, and you are in San Francisco. No problem! Sure you don't feel great after taking a red-eye, but you make it there. And you've set up other back-to-back meetings to get the most out of your time. By the time you are back at the airport you realize you might not have mentioned your whereabouts to your spouse but know he'll understand. And you know that this phase can't last forever, but you must take full advantage of every opportunity now, while you have it.

• Phase 2--The Trade-offs: You realize that other things--hobbies, friends, wellness--are being impacted, but hopefully now you are experiencing some growth and cannot imagine losing momentum in order to stop and smell the roses. Also, expectations have been set. Clients on the East Coast expect that you will be available during the wee hours of the morning on the West Coast; you've told them to call you if they wanted to talk--anytime; they're just taking you up on your offer. All those opportunities that you have been pushing for are now happening; and you must be there to implement them. You can't imagine having others do it during such a delicate, relationship-building phase. You plan to eventually build replicable, delegatable processes, but you must trail-blaze for how.

You try to fit it all in, but even with extended hours you can't. So you compromise on everything except your business. You skip those biannual physical exams, you whittle that full workout into a few sit-ups before bed, you spam an eGreeting card to your address book this year instead of sending individually written cards. That quality time you book nightly with your spouse or the kids is spent responding to email while sitting next to him on the couch. You don't have to meet with people in-person today, so you forgo showering and getting dressed--time is money, people! The first time you skip these things it feels bad; the second time you can justify it as something you're sacrificing "for now", the third time you've re-identified yourself: "I guess I'm just going to be 10 pounds heavier." "I've never been much of a home cook." "I'm just not a neat person." "I'm the kind of person who always has to be doing something." ...

You start to fear that your tradeoffs are becoming more and more visible. You look older. You have creaky knees and your neck hurts. You indiscriminately hand people not associated with your business, like your drycleaner, your business card. You develop this glassy look that signals to your domestic partner that you are assessing what else you need to get done today, not listening to his suggestions for what to have for dinner. You meet up with friends you haven't seen in ages, and when they ask how you are doing, you update them on your calendar and on your competition.

• Phase 3--Signs of wear and tear: You have much to show for your hard work--both good and bad. You are still pushing hard; forget about cruise-control. But you can speak confidently about the future of your business.

Through accidental situations, like delayed flights and malfunctioning electronics, you find yourself with small pockets of unscheduled time and have no idea what to do with it: Pick up a newspaper and at least familiarize yourself with the happenings in the world, pet your cat, or call people? You realize you don't know where to start and defer to doodling in your notebook. You go to the dentist and they declare you're in for a year of orthodontics due to stress-induced jaw alignment issues. You understand the urgency but just don't know how you can fit that sort of thing into your schedule at this time. Pain is also very time consuming--feeling it, preventing it, containing it. You plan another appointment in several months--hopefully enough lead time to plan around it. You later realize that you do have a conflict but you do nothing. Maybe the other party will cancel. You meet up with friends you haven't seen in ages, and when they ask how you are doing, you have nothing to say. You say, "Hanging in, and you?

People call you successful and you wonder, "How so?" Even if you are, you are so used to the act of building momentum that you don't know what success feels like. Perhaps you've overcome it and it's now trailing behind, and you just feel something dragging. You assume it's another problem to attack. You remove your anniversary dinner from your calendar and enter "figure out dragging issue" in its place.

But back to HR Capitalist's two options: Accept that you are going to have to put in the time, or start taking things off your plate. The frustration of a later-stage entrepreneur who's had a few years to cycle through both options is "what else?"

One could say Option 3 is aspire to less. Let's just say for the sake of argument that this was even possible for the entrepreneur, that we could temporarily suppress this unquenchable ambition and could actually make a logical decision to dial it back a bit. I argue that our natures would kick back in, and we would become crazy about something else.

My friend and former coach Kimberly threw something out to me that was similar to Kris's advice, but offered in a way that I could actually consider.

"I'll bet you could back off about 10 percent and no one would even notice," she said.

"But I would notice," I said.

And I thought about that. There are types of effort: level one being "9-5" effort, level two being extraordinary effort, and level three being "Why are you afraid that level two won't suffice?" effort.

I am willing to consider level 2 may be effective.