A brain dump on careers

Last week, I sent a massive brain dump on careers to a couple of college buddies, Sean and Brendan.

Sean and Brendan reached out to me because they are both music teachers who want to enter the business world and I am someone who has done just that. Here are some of the questions they asked me.

Questions from Sean

• How do we effectively present the skills we have developed as music teachers to someone in a business profession, especially if their only experience with a band director is Mr. Holland’s Opus?
• Do you have any suggestions about the question on presenting our skills?
• Do you know of any resources that pertain to this subject?

Questions from Brendan

• When did you realize that a career in music wasn’t for you?
• What steps did you initially take to transition out of that track?
• Did you have a previous background in business that ran parallel to your music performance career?
• Do you feel that you are fairly compensated for the work that you do at your job?
• How can we communicate those skills [associated with running a band program] to potential employers?
• Have you run into these stereotypes [about musicians] before?
• How can we start to break down these generalizations [about band directors]?

Backstory

When Sean and Brendan met me, I was a graduate student in music performance at the University of Illinois. I was completely lost in life also.

Even though I was a teaching assistant on a full tuition waiver, I was also on academic probation and in danger of being kicked out of the university altogether. In the end, I dropped out and entered a dark period of my life.

Fortunately, I found my way out of that dark period and started to move forward. While I still have no idea what I’m doing in life, I at least feel more comfortable with uncertainty and self-doubt.

I wanted to share my reply to Sean and Brendan with you in the hopes that you would get some value from what I wrote as well. Feel free to leave a comment and share your thoughts, questions, comments, etc.

For context, Sean and Brendan are two guys in their late 20s. Bruce is Sean’s dad.

My reply

Hi guys,

Bruce, thanks for sharing your insights. I agree that Sean and Brendan know more about business than they think they do and that there is plenty of opportunity in the world for people who are willing to work hard for a long time.

Brendan and Sean, I admire your courage and humbleness in asking for help. Most people would rather play it safe and stay where they are, even if is no longer the best place to be. The fact that you have both admitted to yourselves that you want something different out of life is a tremendous step forward.

We all know that there is nothing wrong with being a music teacher. In fact, I bet that we would all say that our music teachers were some of the most influential people in our lives growing up. But there are times in life when we realize that where we are is not where we want to be. That is how I felt during my entire year at U of I before I dropped out and entered a dark chapter of my life.

I didn’t know where I wanted to go, but I knew that I did not want to be where I was. I often tell people, “I followed my passion, and it made me miserable.” I was not happy at U of I or in the three to four years that followed. I was lost with no direction, no sense of purpose, no hope. Hell, I was probably depressed for a while.

Over time, I managed to pull myself out of a deep hole and make something of myself. My journey wasn’t easy or fast, but it was worth it. I know exactly how it feels to be where you are. As Brendan said, I have done what you are trying to do. Making the decision to leave the music profession was one of the most difficult decisions of my life.

To be honest, I don’t know how much wisdom I can convey in an email. I actually suggest that we jump on a call to chat, individually and/or separately to talk about your careers. Still, I want to offer you some advice and share some lessons learned. My only ask is that you both pay it forward in 5-6 years when you get an email from someone asking for help. That is what others did for me. I trust that you will both honor that commitment.

To Sean

First, congratulations [on your upcoming move and wedding]! It sounds like you are about to embark on an exciting new journey. Enjoy it, all of it.

It’s okay to be clueless.

I’m going to let you in on a little secret: I have no idea what I’m doing. Everyone seems to think that I have it all mapped out, that I have my shit together. I assure you that I am just as lost as I was when I was a grad student at U of I. I have simply learned how to cope better with uncertainty and self-doubt, which will never go away in life.

My advice on this point is to accept the fact that you are filled with uncertainty and self-doubt. It’s okay. We all feel that way sometimes, even the most confident among us. Use your feelings of uncertainty and self-doubt as a tool. Why do you feel that way? What causes those feelings for you? When do you feel that way?

Walk through a door.

I don’t remember where I heard the metaphor, but I remember reading that life presents you with a wall of doors at any given moment. You cannot see beyond the doors. You know only that you must walk through one of them. So you must make a choice and walk through a door.

You will never get an opportunity to walk through every door in life. You must decide which doors you will enter and which doors you will ignore. Decide carefully but decide and start walking. You don’t want to spend your life staring at a wall of the same doors, feeling too uncertain to walk through any of them.

Fill in the blanks.

Your dad made a great point when he called out the fact that neither you nor Brendan said explicitly what you want to do. I get it. I had no idea what I wanted to do when I left music. I still don’t fully know what I want to do. Like I said, I have no idea what I’m doing either.

That said, I have a framework that will help you. Fill in the blanks.

I want to work for a [size] [industry] company in [city] on the [function] team as a [title].

This is what I mean.

• Size: How large do you want the company to be?
  • Startup: 0 – 50 employees
  • Small: 50 – 100 employees
  • Medium: 100 – 500 employees
  • Large: 500 – 1,000 employees
  • Enterprise: 1,000+ employees
• Industry: What types of products or services do you want the company to sell? (e.g., software, beer, musical instruments, etc.)
• City: Where do you want to work? (This is more relevant for Brendan as he makes his way back to the US.)
• Function: At a high level, what business function do you want to do?
  • Human Resources: You want to deal with people.
  • Finance & Accounting: You want to deal with money.
  • Operations: You want to deal with systems and processes.
  • Sales: You want to sell products and/or services.
  • Marketing: You want to promote products and/or services.
• Title: What is the specific title that you want to have?
  • Don’t worry about this just yet. Focus on the first four bullets first. Once you make a decision about the first four bullets, the title will work itself out.

When I started looking for my last role, I filled in the blanks for myself. I thought, “I want to work for a small Salesforce consulting company in Chicago on the professional services team as a Salesforce consultant.”

It is immensely helpful to create a framework like that for yourself when applying to roles. Why? Because you won’t waste your time on roles that you would hate.

Answer these questions.

• How do I want to spend my time?
• What types of problems do I want to solve?
• Who do I want to work with on a daily basis?

Obviously, there are other questions. But those will get you started.

Regarding your business idea of helping people transition into the business world from the outside, I think there is a market. All three of us are looking to move from music to business. We can talk about entrepreneurship as well. But that falls outside of this immediate conversation.

For Brendan

I realized that a career in music was not for me when I observed my own behavior and asked myself a basic question.

On the behavior side, I did not act the same way that people who were “all in” on music acted. I was not a die-hard musician, and I knew it. But I couldn’t admit it to myself at the time. All my life, everyone told me how gifted I was in music. It was almost annoying. Ultimately, I didn’t care that I was good in music. Yes, I was glad that I was good at music and found enjoyment in it. But I didn’t get a sense of mission from playing trombone. I didn’t get a sense of meaning.

The other factor was my question. I asked myself, “Is there anything that I love more than music?” As it turns out, the answer to that question was yes. Most surprisingly, the answer was business. I love business. Business is endlessly fascinating for me. There are so many different types of businesses selling so many different things. In my line of work, I get exposed to lots of different businesses and fix lots of complex problems. I’ve also had a fascination for technology for a long time, which also fits nicely into my profession.

However, you should not be mistaken. The road to get where I am sucked. I don’t want to deceive either of you. You are both in for several years of hard, painful work. But I know that you can do it because I know that you have both locked yourself in a practice room for hours and hours, beating your head against a wall as you tried to get that lick.

Play the long game because it’s the only game.

Try not to get bogged down in the tactics. I know that you want to know the steps that I took to get from A to B. I’m happy to share those with you. But right now, you need to figure out which way is north. First, plot your points on a map. Then, start walking.

It’s okay to want to make a lot of money.

Brendan, I get the sense that you want to make a lot of money. That is okay. If you want to make a lot of money, go for it. We’re often shamed in our society for wanting to make a lot of money. Why? I don’t get it. Some people want to watch shitty television, some people want to go to Disneyland, some people want to make a lot of money. As long as you do not hurt others in the process, make as much goddamn money as you want. Besides, you can’t give away millions if you don’t have millions first.

It’s important to accept yourself for who you are, not who everyone else wants you to be. Yes, that sounds a bit frilly and woo-wooey. But it’s true. Focus your time, energy, and money on the things that create value for yourself and others. Forget everything else. To be clear, value does not equal money. If you get value from watching shitty television shows, then watch them. If you get value from reading fiction, then read it.

Be weird.

The first step in all of this, for both of you, is to own who you are. Be weird. Find that thing that makes you weird and own the hell out of it. Authenticity is infectious. People love authenticity, especially in a world that’s filled with selfies and people pretending that their lives are so amazing.

Yes, I get paid fairly.

While I appreciate your interest in making money, understand that earning more doesn’t make you happier after $75,000. How you spend your money has a much more significant impact on happiness. Read Happy Money for more on this idea. It’s pretty fascinating.

Regarding compensation, I’m happy to share my numbers with you. But that shouldn’t matter right now because, if you’re not happy at work (or at least content), no amount of money will make you love a job you hate.

Conclusion

We’ll worry about the specifics of getting noticed by employers later. For now, give some thoughts to what Bruce and I have said. Feel free to send follow-up questions as you have them.

If you’d like to chat about your career, I’m happy to do it. Just leave a comment or send me an email and let me know.