10 Past Business Mistakes: How to Learn From Them

Growing up in a household where my father owned an auto parts store, I became drawn to business at an early age. (I wasn’t drawn to auto parts or cars though - imagine that).

By 7th grade, I was writing payroll, doing end of the month paperwork, mailing checks, mailing statements, and selling sweetcorn out of the back of the garage in my free time. Also, I had the privilege of hearing my dad complain about taxes a lot (and he refused to answer the phone once we got home). 

Fast forward ten years, and I was proud to be scrappy and happy with my own full-time music business. However, being full-time didn’t last long (3 years, when my goal was 5).

In my early twenties, I made so many mistakes trying to mix business and art, that the very concept of having a business certainly scared me off for awhile. In fact, I became literally excited about having steady day jobs. My recent stability has resulted in me not pushing myself or taking very many risks, however, and here are a few things I know I can learn from my past.

1. Repeat yourself more.

I dread redundancy. As a musician, I would sometimes know what an audience wanted to hear (even a song of mine!) and I just wouldn’t do it. I’d preferred the novelty of trying a new song, even if it meant messing up mildly in front of others. 

Now I realize, no one expects me to play hits. I’m not some one hit wonder from the 90s on a reunion tour. As a writer, I can still craft something true to me, while realizing redundancy in expertise is part of the game - no matter what profession you find yourself in. I need to repeat what I stand for and what I offer while realizing I’m not boring anyone.

"Every ladder encountered here is a way one. Staying off is the escape."

Hmmm... not the most motivated person.

2. Pitch more and be selective.

When younger, I took whatever came easily in terms of shows and people to work with. I rarely promoted myself or went after what I truly wanted. I never aimed high.

Even when a bigger opportunity came, I usually became internally afraid of it and the added pressure it might bring.

It’s not surprising that I burned out. I viewed the work of “aiming high” as business work that would take away from making the "best" music I could.

Now I understand the value of putting yourself in more appropriate environments to eventually give your art the best chance of survival. 

3. Expand the definition of opportunity.

I didn’t see the potential of the online world or view it as a place for “people like me” until really late in the game. (I guess by “people like me,” I mean artists who didn’t buy iPhones for years until after they came out, people who like to read under a tree all afternoon, people who think they have to be at least five years younger to be caught dead on a Youtube channel, and people happy to walk alone with their thoughts most of the day.)

Likewise, I’d say no to occasional gigs I thought didn’t fit me, only to find myself sitting around all night staring at a screen and realizing I might as well have gone. (At one such event, I actually met my husband!)

Now? The internet genuinely excites me, and I enjoy meeting different kinds of people offline and online. I’m much more open minded. I know you can start looking in one direction and end up somewhere completely different. And that’s OK as long as you know your values and expand your definition of an opportunity. 

4. Try out “side tasks” related to the business.

I was terrified of graphic design and making my own art as a musician (especially album art). I was also terrified of the recording process, mixing, and mastering. My one track mind thought I should write music and never dabble with those other things. 

As of late, I’ve played around on Canva a few times for graphic design. I've found I really like it! Same with quick photography related to Instagram photos. I’m slowly working on my visual appreciation of different brands, and finding I really look forward to tasks that expand my sense of self.

5. Realize things aren’t what they seem.

For a brief moment in my early 20s, I thought I had to live in a city in order to find epically creative thinkers, movements, and art. Before returning to the midwest to become a full-time musician, I moved to Austin, TX and found myself working at a chain store. Don’t get me wrong - I love the vibe of Austin, but as you can imagine, I didn’t go there for retail experience. 

I never imagined how happy I would be finding like-minded people in a small town close to where I grew up. Do you know there are places in San Diego, Portland, and elsewhere where people have to PAY TO PLAY music? That sounds insane to me. I was paid well by people who appreciated me and I didn’t have to tour very far. I’m taking that lesson with me.

Likewise, things aren’t what they seem online. There are people with 1,000 followers or less raking it in with their freelance businesses and/or devoted fanbase. And some people expending tons of time and looking impressive on social media are accomplishing little else on the side. It’s a world of funhouse mirrors out there.

Next week I will discuss struggles with image and presentation, how low self-esteem can drive fans away, and how little things related to your business can add up over time.

How about you? What business mistakes have you made? What would you recommend to someone starting over?

DISCLAIMER: AS ALWAYS, IF YOU NEED PSYCHOLOGICAL OR FINANCIAL ADVICE PLEASE SEEK A PROFESSIONAL FOR YOUR SPECIFIC SITUATION.

2 Replies to “10 Past Business Mistakes: How to Learn From Them”

  1. A great article Michelle and thanks for sharing. As for me, I’ve made so many business (& other) mistakes, it’s incalculable. However, as the adage goes, ‘the person who make no mistakes, does not usually make much of anything.’

    When I look at them, it’s clear that there is a pattern, however, that usually involves doing something for the wrong reason, not believing in myself, or doing what others, rather than me, think is best.

    Thanks a look forward to reading the follow up.

    1. Thanks for sharing Mr. Fate. I like the steep learning curve when there isn’t monetary pressure behind it. I have learned so much in the past two years! Like you, I can identify patterns where I am lost or not keeping my eye on the right things. I enjoy the game though, so I’m in it for the long haul. Stay tuned for part 2!

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