Freelancing is a long game: Why you shouldn’t get discouraged yet

nomadLast Monday morning started off just like any other day.

I woke up around 8am, walked the dog, had breakfast, and since I now work from home, I sat down on the couch with my computer to start the day.

After about two hours of the same ol’ same ol’, an email popped up in my inbox that made me drop everything I was doing.

Just a quick back story:

I used to have another blog called ‘Thoughts from the back row’ when I was just out of college and I was trying to get in touch with people I admired in the music business.

While there were a few successes like sitting down with Ben Zander and Peter Seymour of Project Trio, most people never even responded.

Then two and a half years after the initial email, the person I was most interested in talking to appeared in my inbox…

Alright, back to last Monday.

I look at my inbox and I see that Chuck Daellenbach, a founder of Canadian Brass, is following up with me on an email I sent him over two and half years ago.

Being a total fanboy, I was totally swooning when I saw this email.  

I frantically responded while trying not to sound like a teenage girl freaking out at a Taylor Swift concert and sure enough he responds right back to set up an interview the following morning.

The next day we get on a Skype call and chat for about an 30mins (Sign up here to get notified when I post this).

So anyway, the reason I’m telling you this is because it demonstrates a huge lesson that I’ve been fortunate enough to learn over the past few years.

Building a career in music is a long game.

Whether you’re still in school, a recent grad, or a seasoned pro, everyone will experience something similar to this many times in their career.

Things often take a long time to develop and you never know what little thing will set something in motion that will lead to a great opportunity down the road.

As musicians, we work in a business that can be unbelievably competitive and it’s easy to get discouraged when things feel like they’re moving too slow (or maybe even not at all).

I got passed over for that gig again…

I didn’t advance in the audition…

All of my Facebook friends are so successful…

Something that has worked wonders for me is looking at every place I go, every person I meet, and every opportunity as a chance to plant a seed.

At the risk of sounding like a total cheeseball here, I think it’s an important metaphor as to how things tend to work.

Maybe you’re trying to break into a new scene but it feels like it’s just not working.

The best thing you can do is to just keep meeting people, getting better, and in general just keep pounding the hell out of “the pavement”.  

Once you “plant the seed” you can start to develop a relationship with everyone you meet (watering the seed if you want to continue with this agricultural metaphor).

Here’s a general sequence that I follow when I meet someone new that I’d like to build a relationship with:

  1. Introduce yourself.  (at a gig, via email, whatever)
  2. Follow up with them after you’ve made the initial introduction. (Hey _____, it was great meeting you the other day and I just wanted to say thank you for welcoming me into the section.  I’m looking forward to seeing you around town soon!  -Seth)
  3. Recommend them for gigs or hire them for something yourself

This process could take months or even years to fully play out, but when it does, you’ll have a new connection in town.

If you’re doing the work and always pressing forward, things will start to work.

Freelancing is a long game and if you’re not having much luck with it after a few weeks, months, or even years, it’s OK.


It takes time and I think it’s something we all need a reminder of once in awhile.

It took me over two years to even get a response from Chuck and within 24 hours we were chatting on Skype.  

That random person you hit it off with at your last gig might be a huge contractor in town some day.  

You just never know.

Keep hustling everyone!

About the interview with Chuck Daellenbach

For those that are curious, In this interview we discussed:

  • The very first gig Canadian Brass ever played
  • How they leveraged what they had to work with into bigger opportunities
  • And what he would do if he were starting his career today

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