He wrote back. He was relentless, so I asked him to tell me a bit about himself. He wrote, among other things, “I’m the guy you want to date.”

It was such a direct response. And I like direct. Plus, he was going to be in Madison. That never happens.

Two days before the date, I checked him out on Facebook.

Then I wrote him an email. “You are way too young. I can’t go out with you.”

He wrote back, “You should know more than anyone else that online identities are deceiving. And anyway, I’m older than you think.”

That was a good response.

So we agreed to meet at a diner. For coffee. I walk in, and right away I know who he is: The guy with the backpack.

We sit down.

I lean across the table, and in a low voice I ask, “How old are you?”

He says, “I knew you’d ask that.” He says, “Twenty-five.”

I look around to see if people at the diner are staring at us.

He is surprisingly interesting. He’s semi-pro in an odd sport, and he has a business plan to create a quirky application for the iPhone. We talk for an hour.

Outside he says, “I’d like to see you again.”

I think that’s hilarious. I mean, I can’t believe a 25-year-old wants to see me once, let alone again. And I can’t imagine how things will unfold. So I say, “Okay.”

On the next date he knows the chef of the restaurant, so I think he does not totally have to pay for dinner, which is good, because he doesn’t have the kind of job that could pay for this kind of dinner.

We talk about social media. He tells me about conferences he goes to in warm places with hipsters who live and breathe technology. Topics like iPhone applications for crowdsourcing get me excited. I am a sucker for someone who can teach me something.

After dinner he wants to go to a bar. We walk to one he can’t find, and I am freezing and complaining and he slips his arm around my waist.

I think it was warmer with his arm there. Or maybe my body started sweating from the stress of walking through Madison with a twenty-five-year-old.

The bar is loud. I lean over, close to his cheek, and say, “I have to leave now. My ex-husband is with the kids and I told him he could leave at 10:30.”

The twenty-five-year-old looks at me.

I go on. “Maybe we need a plan or something. I mean, I need to either drive you back or drive you to my house.”

He says, “Let’s go to your house.”

In the car I tell him it’s crazy to take him to my house.

I look over at him. He looks back.

“Okay,” I say. “Okay. My house.”

In the car I imagine him at my house, and he will have to take a cab home, and it seems like a pain. And the potential for awkwardness is huge.

At a stop-sign on a dark road, I say, “I’m turning around and taking you back.”

He takes his seatbelt off, leans over and kisses me. It is a very good kiss, slow and soft, and a little bit wet. And it seems very hard to do that when the whole rest of the evening is riding on one kiss. I reward him by heading toward my house.

My Ex is at the house when we walk in. The guys I work with are the same age as the twenty-five-year-old, and they’ve been to my house late at night many times, so my Ex assumes I work with the twenty-five-year-old and he’s chatty.

When the Ex leaves I take the twenty-five-year-old into the kitchen. I tell him, “It’s my son’s half-birthday tomorrow. He needs cupcakes for school. I have one more batch to make.” Then I start dripping gooey batter into superhero foils.

The twenty-five-year-old is patient. And anxious. I sit on the counter and watch him watch the cupcakes, and then when he’s within reach, I scoop him over to me with my legs.

We cannot kiss too much because there’s no extra batter if this batch burns. I am focused on cooking.

Then we go upstairs.

When he pins me against the wall, our age gap dissipates.

Fast-forward: I have seen him again. Though not a lot.

I’ve seen him enough to get flashbacks to when I dated guys a lot farther along in their career than I was. It was exciting. They knew a lot more about sex than I did, but you equalize on that pretty fast. And then, what’s left in the inequality department is career stuff. And I could always figure out how to get stuff from them.

It was exciting to be the young girl who the older guys want to help, and date. At the same time. I was never sure how much I wanted either offering, but I knew that together, they were intoxicating. I want to see what that’s like from the other side.

I am nervous with the twenty-five-year-old because of that. He asked me why I’m not following him on Twitter and I told him I forgot. But I didn’t forget. I read his feed all the time. But I didn’t want to look like a stalker, because so many times in my life, the older guys felt like stalkers to me.

The twenty-five-year-old asks for a lot of advice with work. He is, after all, working in my field. Almost everyone he has needed to get in touch with is someone I’ve had lunch with. I’m also very hesitant to ask friends to help a guy I’m having sex with. In the past, when I have seen executives do this with marketing girls (I have seen this a lot, actually) I have been embarrassed for them.

So I have not helped him that much, honestly. And in bed one morning I say, “How come you haven’t asked me to get you a job?

He says, “The thought’s occurred to me. I figured it would eventually come up.”

I don’t say anything. I don’t want to help him get a job. I want this to not be about all the stuff I could do for him. But all the older men I dated when I was his age were people who helped me with my career; they it did gracefully, and I was so thankful.

I started writing career advice because in my career I found myself constantly in situations that made the old workplace rules seem irrelevant. I realized the workplace had changed, and I wrote advice as I lived through it so the next wave of workers would have a relevant guide.

Today I have an amazing network of men and women who help me guide my career. But periodically I find my career lands me in a spot I have not been before. Right now I feel clumsy. Like the people who write long emails to me, thinking I have not heard their career problem before.

When I started writing career advice, the questions I answered were is job hopping bad? Is being lost bad? Today I find myself wondering: When women get power at work, do they use it like men do?

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This is enough for him to have a private jet and be King of Madison (Wisconsin), but not enough for him to get a lot of respect in Silicon Valley. A quote from my advisory board member who lives in Silicon Valley: “For big VCs, $50 million is a rounding error.”

So Brian is not looking for people to mentor or boards to sit on because he is consumed with running his fourth company, Alice.com, which will compete with Wal-Mart and Target.

I do not tell Brian that I will have a hard time ever missing a trip to Target to shop at Alice because Target has such great clothes that are so cheap they are almost free.

Well, actually I did tell him that. And I told him a bunch of other stuff, because I decided that I need him as a mentor. Eventually, I got him to agree to be on the board of my company. Here’s the process I took to convince him to help me. And these are good steps for anytime you have someone you’d like to ask to be your mentor:

1. Don’t be discouraged by lack of response.

The way Brian operates is that he doesn’t talk to anyone in Madison and I had to send him fifteen emails before he’d have lunch with me.

Later her told me that he gets so many invitations for lunch that he doesn’t even respond until someone sends him two emails. “They have to show a little tenacity,” he says.

2. Find the person’s weakness, so you know where you can help him.

When we had lunch I opened by regaling him with stories of my dating life, to make him feel a little unstable and vulnerable. And then I launched into how he needs to help more entrepreneurs and he is helping no one in Madison and it’s not enough to be great at building companies. “You need to be great at building communities of people building companies,” I told him.

He looked at me with an incredulous stare.

“It’s more fun that way,” I said. “We’re doing this for fun, right? I mean, you do not need more money. So there is no rational reason for you to be working insane hours for another company. And I do need a lot more money. And it would be much safer for me to go to a Fortune 500 company and draw a big salary than take a risk on a startup. So we’re both doing this for fun, right? And it’s more fun if you help more people.”

Brian pointed out to me his companies made several people in Madison millionaires.

Immediately I wish I had met him earlier. Like, when I was scooping ice cream at 31 Flavors and I could have been getting him coffee in exchange for stock options.

We come to an agreement that he will help me because he wants to be a good and giving person and I promise him that I will be fun.

3. Be real. No one wants to mentor someone who is perfect.

I then proceeded to be totally not fun by running out of money, being moody and difficult, and totally pissing off my lead investor who is also one of his investors. To the point where Brian told me that he couldn’t be associated with my company. Because we were in too much trouble.

He would not agree that he said that. I am summarizing. But this is really the crux of the whole problem: He is the paragon of diplomacy and I am not. And I need to be. Because we live in a small town. And all angel funding is local.

But while I was melting down, he was paying attention. For the first time, I didn’t have to chase him – he was genuinely interested in how I was getting out of my mess.

4. Remember that good advice is harder to find than money.

Speaking of melting down over money, you’d think it would be totally annoying to me that he’s not putting money into my company. Because money is local. And he is local. And he is money.

We talk about this over lunch. And he is paying for lunch. That’s a good start.

It’s our third lunch. I pace myself for topics to cover. I try not to think about the fact that he gets a little antsy at the end. Like, he just sort of gets up when he’s done. Other people kind of wind down the conversation. Or do something like fold their napkin. He just stands up. Sometimes I’m mid-thought.

I am one of the most socially awkward people I hang out with, so it takes a lot for me to be making remarks about someone else’s social retardation. But the truth is, though, that entrepreneurs are often described as quirky, and Brian’s weirdness makes me trust his advice more.

Brian gives great advice about the nuts and bolts of running a company. After all, once you’ve done three, you have to have sort of a system for going the distance, right? He is great for keeping me focused. I am always thinking about the future – where is human resources going? Where is generation Y going? Where is blogging going? I am asking the huge questions instead of “Did anyone call Deloitte to find out what they are posting on Brazen Careerist next month?”

Brian says something like, “What are you doing to make sure that everyone in the company is focused on the same vision?”

5. In the end, you want the mentor to care about you as a person.

I knew things were going well when we were talking about how to make payroll and Brian said, “Wait. One more thing. You have to get rid of that farmer.” (And I’m thinking, “Brian, when you are walking through the parking lot for your private jet, why don’t you look around for someone better for me to date?”)

The great thing about Brian is that he’s exited enough startups that he can afford to be light. For isolated moments. Most entrepreneurs are anxious during the early phase of a startup. Obsessively focused. Tweaking models often. Praying something sticks.

Brian is steady though – he knows he’ll figure it out. When it comes to building a company, Brian has the perfect combination of calm and excitement. And in the end, I think he might be my mentor for being lighthearted and calm. Or faking it.

You should try to get a mentor like Brian. But since you probably won’t get one right away – after all, you need at least fifteen emails – you should subscribe to his Twitter feed. Which I love. It’s a peek into how a startup unfolds in an entrepreneur’s brain.

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In the meantime, I’m thinking about the day of service. How Obama wants the country to come together in the name of service. And I heard MTV declare, last night, that the next generation is Generation S. For service.

So I’m thinking about service, and how all our efforts to help people, really, are aimed to make them more indepdent. And that’s what work is about: Taking care of ourselves, mentally and financially.

When you mentor someone in the work arena, you are providing that service. So often we pick the superstar to mentor. Or the up-and-comer. Or the one who can help us with our own networking. But you can use your work skills to help someone pull themselves out of a bad spot. A really bad spot. Work skills are very powerful. And so is mentoring.

So when you think about service, don’t’ think of it as separate from work. Obama stands for all the things that we do, on this blog: Personal responsibility, transparency, honesty, change even when it’s difficult. This inagural day is the beginning of meshing the public life and worklife so that we are living the values we believe in, wherever we go.

Think about how you can focus on service at work. Each of us has a lot of tools at our disposal. If we take the time to use them.

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She did a great job. She memorized speeches that she trotted out in good moments. And she had such nerve! Most of us would be too shy to flagrantly disregard the question, but she knew that was her job. She knew her job was to give set up answers and fit them in the best she could, and she did that. She delivered her lines very well. She played to the camera. She was friendly, and charming, and eloquent as long as you didn't mind that she talked about whatever she wanted.

The thing is that most of politics is not about giving the right answer. It's about giving any answer the right way. The world is not bashing Kennedy for beating Nixon in the classic debate where Nixon wore all the wrong stuff and the wrong makeup and could have said anything and he still would have lost. No. No one is complaining about Kennedy's dependence on style in that debate. And we didn't generally bash Reagan for being a great orator even though we thought he was probably losing his mind even before he got to office. He was still a great orator and could deliver his messages in a mesmerizing way.

So give Sarah some credit. She did a great job. Sure she's probably not ready to move into the White House. But that doesn't mean she didn't do a great job. She can only do her best. And she did. And you have to respect someone who takes a huge risk and does a good job. Look, if you think she's unqualified, don't vote for McCain, because he's the bozo who selected her. But since she's there, learn something from her. Take advantage of a fun, capable woman who is rising up to the occasion. She's ignoring the taunts (even I have thrown some) and she has enough of a sense of self that she's plowing forward.

But really, it's hard to believe that she will be on the winning ticket. It's hard to believe that anyone could choose McCain after he has shown such poor judgment. But Palin will land on her feet. She'll get some TV commentator job, or some interior secretary job, and she'll learn the ropes, and she'll succeed.

If you are wondering why your own career is stalled, consider that it's because you don't have mentors like her. She is scrappy and she knows how to manage her image. It's not small peanuts, and it's hard to find a woman who is as good at it as she is and public about how she's doing it. Take advantage of the learning opportunity.

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Jim teaches creative writing at Santa Monica College, (and his faculty page reveals so much about him). He lets anyone join the class, but you have to read your writing out loud. This weeds out almost everyone. Because first you have to write something. And then you have to let everyone rip it to shreds. In front of you.

But wait. It gets worse. Because Jim edits. He slashes most of the writing he reads. And then, if you're new to the class, you assume he's wrong, so you read out loud what he has cut and you hear it fall flat as soon as it leaves your lips.

Try it. Read something you wrote out loud to a friend. If it's bad, you'll feel right away that boredom has overcome the room. If you have even one flat sentence, you hear it when you read it out loud.

The first time Jim heard me read my writing, he said it was the best he’d heard anyone read in his class in a long time. Then he slashed everything I wrote for the next six years. Sometimes I'd hand in three pages of writing and he'd leave only five sentences.

But this is the thing about those five sentences: they were great. And here's why I became a dedicated follower: Because I felt like he understood my compulsive need to write my life. And I understood his goal, which was to have interesting sentences. So when he cut full paragraphs that I thought were important because my sentences were boring, I felt grateful that he saved me from banality.

And I channel him every day that I write a post. I think to myself: Is this sentence one that Jim would cut?

I am not so arrogant as to think that Jim would even bother to read any of my sentences today. But I do know that the lessons I learned from Jim are the essence of good blogging. You can’t be boring on a blog. People will stop reading.

So if you want to know how to write interesting paragraphs, read the authors who are famous for their ability to stun sentence by sentence. Try Jim Krusoe. Try literary types who sacrifice plot for prose: Ken Sparling, Martin Amis, Ann Beattie. (And, when you are feeling ambitious, Marcel Proust.)

I tell people all the time to pick a mentor rather than picking a job. Jim Krusoe is my first experience with this. He didn't teach at a college I had ever heard of. And he didn't even write books that I understood. But he is legendary for churning out well-respected writers, year after year.

Find a mentor with this reputation, and then work hard to make sure you each understand each others' goals. What you'll get out of this relationship is a new way to be more of your true self. And this is the best kind of job we can ask for.

We don't have to find our true calling from a mentor. In fact, what I found from Jim was confidence to think that I should keep writing and see what happens. A good mentor opens doors, in our minds, and you can find that at any job, any company, anyplace your connection with someone is strong.

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Eland gave me a seven-step plan for finding mentors (yes, you need a small group of them). And since then, I've written about other aspects as well – mostly as a way to keep myself focused on the task because it's so important and so difficult.

Getting mentors is difficult because it's just like dating: You have to invest a lot of time in a lot of people to find the ones who will really change your life. Over the years, I've had lots of different types of mentors. The eccentric CEO who showed me that success does not preclude weirdness, and my secret mentor who popped up unexpectedly. But the one I am feeling best about right now is a guy in Palo Alto, Chris Yeh. He turned out to be a real gem, so I'm going to tell you how it happened.

1. Recognize someone who thinks in ways that complement you.
I was interviewing a guy for my column in the Boston Globe, and I asked him, as I often do, if he had any friends who would be interesting to talk with. He gave me Chris Yeh's name. I was immediately struck by Chris's ability to talk on a wide range of topics that I care about a lot. And as a Harvard Business school grad living in Palo Alto, he brings a fresh perspective to my own.

2. Do favors. Again and again.
I immediately thought to myself, what can I do for Chris? I asked him what he is aiming to do next, what his plans are for the future, where he's headed. He said he wanted to write a book about fatherhood, so I put him in contact with my agent.

3. Stay in touch continually.
I did not actually do this myself. Chris did. He would call at random times, just to say hi. I know very few people in business who do this. Most people email or IM, or, if they really want to talk on the phone, we schedule a call. Chris was different—I was not really his friend, and we were in different time zones, so he made the effort to figure out when I was most likely to be able to talk. Now I see that this as a super smart approach I should have initiated myself to build the relationship.

4. Ask for a formal relationship.
When I started my company, I asked Chris to be an advisor. He said yes, and then he told me the best way to use advisors, based on his experience at his own companies: Call at times you know are easy for them to talk, keep them up to date, and ask them what you should be asking them about.

The first time I asked Chris, "What should I be asking you now?" I felt silly. After all, it's a line he fed me. But now I use it with him all the time, and it's actually an invitation for him to tell me what he thinks I'm missing, which is information I wouldn't get if I directed the conversation the whole time.

5. Invest time.
I had talked with Chris for hours and hours without meeting him in person. When I interviewed Edward Hallowell about his book, Crazy Busy, he described his research about face-to-face contact—how meeting for a just a few minutes changes the nature of a relationship. So I decided to meet Chris in person. On a trip to Los Angeles, I decided to fly to Palo Alto especially to meet him.

The trip took a lot of time, but I discovered that, true to what Hallowell says, meeting in person makes the relationship feel qualitatively deeper by virtue of the fact that you get that whole other layer of nonverbal communication.

Addendum: I called Chris this morning to make certain it was okay to use his name in this post. And he said "Sure, and tell people if they can't find a mentor, they can ask me questions—and you can link to Ask the Harvard MBA." So there's the link. And see, I told you—you have to keep doing favors.

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On 43 Things, 21 people want to learn to take criticism but 77,000 people want to get a promotion. You know what's wrong with this? The way to get a promotion is to take criticism well, but most people don't know they don't do it well.

Everyone knows they are supposed to get a mentor.  And in fact, getting a mentor is one of the best ways to get a promotion. But few people understand that the best way to get a mentor on your side is to take criticism well. This means not only hearing it, but acting on it immediately, and reporting back to the mentor that you have done that.

Which means that a key to finding people you can learn from is finding people you can take criticism from. There's a great discussion on the blog Vineograph about how hard it is to find critics to trust. This is as true for wine recommendation as it is for career recommendations.  The conclusion on this discussion is that you have to know a bunch about the person before you can decide if you trust their criticism. But before you trust someone, you have to start listening.

So I listen to tons of people, always looking for new, competent critics who I might be able to turn into mentors. People always ask me how I deal with so many negative comments on my Yahoo column. The answer is, I read them looking for good critics because you never know where you'll find them.

Do not choose your critics because they are the best at constructive criticism. Your best critics may be totally undiplomatic; you need to find the people who best understand your best attributes. If they understand your strengths, then they understand when you're not using them.

For this reason, I listen to Michael Kemelman who blogs at Recruiting Animal. He rips on me all the time in his blog. And he rips on people I publish, like Ryan Healy. But Michael is smart (and funny) and I have always known that he understands me even as he makes fun of me.

Last week he confirmed this. He sent me a list of four of his favorite posts, and the list means so much to me because they are posts that are only at the very edge of career advice, and they are my favorite kind to write.

So, here's the list of favorite posts from one of the harshest critics I listen to:

The Fine Line Between Boasting on a Resume and Lying

Choosing Between a Kid and a Career

Happy Passover from my Blended Life

Confidence Boosters that Work for Me

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In this environment, training is worth more than a promotion or a raise, and in fact, you'd do well to make a trade if someone offers you either. Training is the new currency of the workplace. Here are four reasons why:

1. Promotions are stressful.
When you get offered a promotion, it's supposed to be a reward for good work. But in fact, most promotions derail you.

Think about it: You're creating a career path that's customized to your skills, strengths, and personal goals. How could anyone else create a path that's right for you? Unfortunately, most companies structure a single corporate ladder and promote people upward whether it's good for them or not.

In fact, most people do good work and then get promoted into a position they've shown no aptitude for. This is most pronounced when, say, a creative person or technical person gets promoted into management. In fact, most promotions are so misguided they're more stressful than divorce.

2. Raises are negligible.
What do you get in exchange for taking the huge risk of leaving something you're good at to do something you're unproven at? What do you get in exchange for derailing your personal plans to follow someone else's path? A 3 percent raise (on average), or 10 percent if you're lucky.

Let's say you get a 10 percent raise. If you're earning $50,000, that's $5,000. After taxes it's around $3,500 — if you even stay in the job for another year. That amount of money won't change your life, and even if you think it will, consider all the extra hours you'll be working because you got promoted.

Read the rest at Yahoo Finance.

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However, the majority of people I know are not great at seeking out and developing these relationships. What I have learned in the past few months is that it's easier than you think! Here are three things I have done that have helped me develop very rewarding relationships with mentors.

1. Find the right network
For twentysomethings, the easiest place to look is in your parent's network. Take advantage of it because they've been developing these connections for years. Ask your parents if any of their friends or colleagues work in a field you are interested in.  

If you are not lucky enough to have well connected parents, all is not lost. Networking groups are everywhere these days. MeetUp.com gives you a way to find people with similar interests. Or you can start a niche blog and comment on blog posts from field-related experts. Leave a few insightful comments and your foot is in the door to contacting them.

2. Reach out
Once you have made the first connection, the next step is simple. Reach out with a short email. Ask for a few pieces of advice. Assuming your contact replies, continue the conversation for a few days. Finally, ask if she is interested in meeting up for a quick lunch. Despite the ease of connecting online, face to face interaction can make a big difference in how quickly you make your mentor feel connected with you. At the very least, try to have a relatively long phone conversation to get to know each other.

3. Think in terms of frequency
After a face to face meeting and a few emails, you should be able to tell if your contact is a potential mentor or advisor. If she is, don't be afraid to bug her! This is always the hardest part for me, but it's the only way you can develop a good relationship. Send an occasional email or call with a casual, not extremely important, but honest question once in a while.   If she is truly annoyed by this, then it's probably time to seek advice elsewhere. But for the most part, I have found people genuinely like to help, especially older folks. The more contact you have, the stronger the relationship will be and the more interest your advisor will take in your career.

Finding a true mentor can take a long time, but almost everyone will offer advice and guidance if asked politely.   Corporate cultures that encourage collaboration between young and old are absolutely necessary, but the responsibility of developing these relationships is in the hands of young workers.   Reach out to someone.  Take a chance.  The details will work themselves out.  

Ryan Healy's blog is Employee Evolution.

Other Brazen Careerist posts on mentoring:

7 Steps to finding and keeping a mentor

How to ask for mentoring

You need a mentor now, here's how to get one

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The weeklong getaways that run a day or two over, the hour-long siestas that turn into three hours, and the three-day weekends that go on for four can all help your career. You just have to use the time well to take care of your physical and mental health.

Why? A healthy body makes for a healthy, balanced mind, and that's the chief asset of a truly good worker. It's not about the hours you spend behind a desk – it's about what's going through your head while you're there.

Here are four ways to ensure that your summer fun in the sun enhances your career success, whether you're still on vacation or are back from one:

1. Go for a run in the park, or swim in a lake at sunset.
It used to be that working out was optional. Now we know that regular exercise makes you calmer, smarter, happier, and richer. So how can you possibly say that it's not one of your highest priorities?

It makes sense that if you feel better about yourself and the world you'll do better in business. Because business is about thinking clearly, acting with confidence, and making good connections.

But don't work out just because people who work out make more money. Do it because it'll change your outlook on life. Really. You'll be less likely to be depressed and more likely to be optimistic.

If you're younger, join an athletic team. People who play sports do better in their careers. This is true whether you're on a small liberal arts college fencing team or a Big Ten football squad. The self-confidence, teamwork, and drive that athletes display makes them higher performers at work.

Sure, there are exceptions, but the advantage is so pronounced that some corporate recruiters at colleges ask to see only the athletes.

2. Mentor a summer intern.
Each of us needs mentors to guide us through our careers at different points in time. Sometimes we need help navigating office politics, sometimes we need advice on making a life change. At each point, knowing how to ask for help is essential, and the best way to learn how to ask for help is to give help.

If you mentor someone, you help yourself as well. You'll find out what a mentoring relationship is like from the other side. For example, you'll learn what feels useful to the mentor and what's annoying. You'll also discover why it's important to ask good questions, because as a mentor you're helpless if the person you're trying to help doesn't know what he wants.

Summer interns are ripe for this task. They're there because they want to learn. You can teach them not only about the workplace but about themselves, and how to figure out where they fit. You can be an advisor and a coach and a friend. These are all great ways to mentor, and after the experience you'll have more confidence in seeking a mentor of your own.

Read the rest at Yahoo Finance

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