The update about my friend Melissa is that she is still working in an administrative job that is totally unimpressive. By choice. Because the only way to know what you’ll like for sure is to try it, so building a career is an exercise in trial and error. Which is what Melissa is doing. And even though trial and error looks very similar to aimless flailing, it’s what everyone has to do. Here’s how to do it well:

1. Let yourself try things that are widely seen as lazy and indulgent.
Melissa was great at everything when she was a kid. She was a math major in college while she was teaching herself to be fluent in Mandarin. She got a job in investment banking.

But really, she just wants to lay in bed and read the New Yorker, (which is actually a common response to childhood in the land of the gifted). Melissa is engaged to Steven, who has a dog that is probably a better catch than he is. This is not to say Steven is bad. He’s good. But his dog is really good. Super smart and well trained and, the best part for Melissa: very needy. The dog waits for Melissa to get home from work and then they get into bed and cuddle and read old New Yorkers.

Which reminds me of when I graduated from college and all I did for five years was play volleyball and read. I read a book every night. I was so excited to be able to read whatever I wanted instead of being crushed by assigned reading. There is this window in life, between graduating from college and having kids, when life is a library.

If that thought resonates with you, you will love this book: The Night Bookmobile. Melissa sent it to me. As a gift. She didn’t add a card, so I assumed the publisher sent it to me for review. And I loved it so much that I sent a copy as a gift to Melissa.

2. Figure out what makes you special.
What Melissa is doing, besides reading and trying to figure out how to get married to a fiance whose mom wants a Catholic wedding to a Jewish girl, is trying to deal with the disappointment of not wanting to have a huge job. But the thing is that very few people have the type of personality that will be fulfilled in a huge job.

Melissa has Asperger’s, which, in her case comes with a photographic memory. There are some things a photographic memory cannot help with: how to tell Steven’s mom she is not going to baptize her kids. But there is a lot a photographic memory is good for, like making tons of money in banking, which Melissa ruled out because of long hours.

3. Get other opinions. All top-performers have lots of coaching.
Naturally, Melissa gets free career coaching from me.

Well, nothing is free. She bails me out of disasters. Like, when I was in Boston with my kids and no money, Melissa left her job and walked to the bank to put money into an account for me.

That’s a picture of her bank lobby. One of the reasons Melissa’s job is good for her is that she can bring her dog to work.

4. Recognize the difference between a career and a hobby.
I told Melissa that she should leverage her photographic memory to do a job she would actually like. She is experimenting. She launched an Etsy store.

She specializes is mid-century modern. I would not say Melissa has a great eye for design, but she is great at memorizing what everything is worth, and she knows what’s under-priced. The problem is that she is very excited about decorating her new house and it seems to me that the Etsy store has morphed into a holding ground for the stuff she is about to put into her house.

Here’s the result:

The problem with the Etsy store idea is that it doesn’t scale. She’s never going to make enough money to pay for the (eventual) childcare she’d need in order to run around Austin sourcing mid-century modern stuff from design-deficient sellers on Craigslist.

“You can’t keep building the Etsy store,” I told her. “It’s not a business. It’s a hobby.”

5. Take suspiciously awful opportunities. They might lead somewhere good.
Luckily, Melissa grew up as a rich kid (whose mythical trust fund is tied up until she can figure out how to create a life her dad likes, which, frankly, will be never when we are starting with a junk shop online and New Yorkers in bed). In case you don’t know the benefits conferred on rich kids, here’s a snapshot:

Melissa picks up her phone and it’s her mom’s friend. Her mom is a doctor. Her mom’s friend is a lawyer. And her mom’s friend has a client in the Middle East who has a textiles business, and a meeting set up with Nordstrom to sell stuff to them. The lawyer wants Melissa to represent the textile firm to Nordstrom.

Not that Melissa knows anything about textiles. Or the Middle East. But so what?

She decides they need a lookbook – which is how you pitch high-flying buyers on products that have to look expensive and precious. Melissa is a great photographer who never markets herself, so it’s the perfect storm.

She takes photos of the stuff. With her friend who is not a model but looks like a model because all girls who go to expensive private schools look like models.

Then, at Nordstrom, Melissa meets all sorts of budding entrepreneurs who need lookbooks. Melissa makes the sale to Nordstrom, because Melissa can sell anything if she tries. Then she collects all the business cards of people who want Melissa to photograph their product.

Just like that, Melissa has a new, exciting job.

6. Forget conventional ideas of a good job. A good job feels good to you.
Then she goes back to her hotel and sleeps. For a day. Then she goes home. And she is so happy to go back to her job, which, previously I have said is sort of a stupid job, but it’s a job that is routine and predictable, and the people are really nice, and Melissa likes it.

Melissa wants to just get married and have kids. But she knows she would be bored staying home all day with kids. She is trying to figure out where the engaging, not-so-intense jobs are. They are hard to find. Intensity and engagement usually go together.

In the meantime, while she’s figuring this out, she’s going to be a guest moderator for the webinar I’m giving next week: Start Your Own Business! You should sign up for that.

To be honest, I helped Melissa start her own business three times. We got funding for her company, but then she didn’t like the high-risk nature of a start-up, so we didn’t do it. She said she wanted to turn her photography into a business. So I showed her how to do that, and we got it all set up, but she realized she hates marketing herself. Then we made a plan for her to turn textile sales into a consulting business.

But she doesn’t want a business. She wants to work for someone else. Which is, actually, much more common than you think. It’s just so unfashionable to admit that.

You never know, really, if you want a business until you have a business sitting right there that you can run. I think that’s the best thing I can teach you in the webinar: how to learn about yourself and how to figure out what sort of work you need day-to-day to feel fulfilled. For so many people, trying to launch their own company is a really important part of this self-exploration.

Back to Melissa. She’s the guest moderator on Thursday night. She will be great. Because she’s great at everything she does. I will ask her to do it again on the Friday session, and she’ll say no. We don’t know why she’ll say no until she does Thursday. That’s the best way to know what you don’t want to do, right? To try it.