“Your work is to discover your world and then with all your heart give yourself to it.”
― Siddhārtha Gautama

I went on a Herman Hesse kick when I was 19 years old. I read Narcissus and Goldmund, Siddhartha, and etc. All great stuff for some young guy desperately trying to figure out what’s the purpose for himself and how to be deep.

That quote up top was lifted, paraphrased, or recycled in a bunch of entrepreneurial/startup books I’ve read since. It sounds like a platitude. Which doesn’t invalidate it: a phrase set in our viewpoint as conventional wisdom means that it proved itself out through the centuries and the mass of people reflecting on it.

But back to the matter at hand: people need to really work to figure out what they want to do.

Most people I know don’t know what they’re doing.

And I mean that. I have friends, family, and colleagues who stumble from gig to gig, job to job. They’re not doing what they love, but there’s love in what they do, so they pass on making hard choices. Someday, someday they’ll figure out what they want or they’ll just….give up trying and hope wherever they landed has good benefits and isn’t a pain.

I urge those people to make some serious choices and pick a direction. Here’s some things I learned when making difficult choices.

1. It’s better to be running TO something than AWAY from something
2. The grass is not always greener, even when you get your dream jobs
3. Dream jobs don’t exist. You are ever-changing; your job either needs to be ever-changing with you or you will have to seek out a new career every time you grow out of the old one. Expect this.
4. Always negotiate, haggle, barter, fight

It’s better to be running TO something than AWAY from something

Before D&T I took jobs based on if I could make more money. And not surprisely, every next job was worst than the last. I had more responsibility, more money, and I was in demand for my skills. Job offers were coming weekly. To this day I STILL get job offers for Revenue Management positions. D&T was the only thing I actually worked to get, rather than have job offers thrown at me and take whatever paid the best.

The grass is not always greener, even when you get your dream jobs

Working at D&T was/is the hardest job I’ve ever done. The last two years were the most stressful I’ve ever lived. Whenever I hear entrepreneurs talk about the times back when their company was 2-5 people, and everyone’s pulling together, and no one’s making money, and they actually GLORIFY that lifestyle, I want to take a flamethrower and torch a building. There is nothing, nothing, nothing, I repeat nothing great about that time in your life. I met Julie those years, and I almost lost her during those years. I gained 35 pounds, lost close friends, and I drank constantly.  And this is my dream job, people. This is what I ran TO, not from.

Dream jobs don’t exist. You are ever-changing; your job either needs to be ever-changing with you or you will have to seek out a new career every time you grow out of the old one. Expect this.

This kills me. People think there’s a magical dream job out there that will be 100% fulfilling in all ways and they’ll never have to worry about another job. That job doesn’t exist. Here’s why: People take on different roles in their lives. You start as a child, then a student, a young professional, become a parent, retire….and all along the way your role changes. Moreover, you’re constantly learning new skills, knowledge, and experiences. To say that you just want to do exactly what you’re doing today, for the rest of your life is akin to saying “I just want to be a parent for the rest of my life”. Someday kids grow up. What are you going to do then? As you get older, hopefully you’re also going to keep learning and growing. Otherwise you’re going to be fated as a boring conversationalist at the party.

Always negotiate, haggle, barter, fight.

Only you can know your own best interests and properly defend them. I do not have my employees’ best interest in mind. I do not have my brothers’ best interest in mind. I only have my best interests, because I know me and what I want. People don’t take the time to make up their mind on where they stand (yes, I said this before but it bears repeating). And we’re not talking about skills or work anymore: this is about life. I once dated someone who always made the plans for us. I just sort of…tagged along. I got pretty upset until I realized “you know, she’s the only one bothering to put a plan together…” Me just saying “naw, let’s not” isn’t a plan – it’s a reaction. Be ready, willing, and knowledgable to fight for whatever it is you want to do. One caveat – fighting does not mean being aggressive all the time. Fighting for a decision can be the difference of an emotional argument and a principled debate. One tries to defeat the opponent, the other seeks to create new knowledge from which a decision by both sides can be made.

In summation: good luck and sorry for the wordiness this time.