Let me tell me.

Sharing a few lessons learned about writing with myself.

Recently, I was asked if I would be interested in sharing my writing wisdom with someone looking to pursue a similar career path. Of course, I agreed because there is nothing old writers like more than telling young writers how to do stuff.

After dropping nearly 20 years (I know, right?) of knowledge on this would-be wordsmith, it hit me that a lot of what I told him would have been great to hear when I was just starting out. So, just in case we invent time travel before Medium stops being a thing, I thought it would be a good idea to write down three things I wish someone had told me way back when.

#1: Failure is your friend.

Look, I’m not going to sugar-coat it. You’re going to be a terrible writer for quite some time. The learning curve for this business is STEEP. You’ve spent most of your academic life being praised for your talent. Now everything you write comes back bathed in red ink. It’s jarring. But failing repeatedly is how you learn to be better. Each “REDO” is another chance to hone and refine your craft. I know you think your words are perfect as is, but you’re wrong. Rewrite. Rewrite. Repeat.

#2: Don’t be Fred Flintstone.

Special things happen after hours at a creative agency and if you clock out at five, you’re missing out. During work hours, you’re just a junior copywriter proofing annual reports. At night, you could be trading tag lines with the creative director. Staying late exposes you to new experiences and opportunities. Hang around…happy hour is overrated anyway.

#3: Your work. Your words.

This may be hard for you to hear, but you have an unhealthy crush on your portfolio. It’s creeping people out. In every interview, you smugly hand it over, watch them quietly (and quickly) flip through it and then wait for the praise to come pouring in…and it never does. Then you sulk back home wondering how they didn’t “get it.” Stop it. Interviewers see dozens of portfolios a day. The only way you’re going to stand out is by speaking up. Background and context are your best friends. Explain the ask for each piece. Walk them through the “why.” Nine times out of ten, the stories behind your work are more important than the work itself.

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What advice would you give younger you about writing? Stay tuned to hear what other creatives had to say. Their answers might surprise you…but probably not (man, I suck at clickbait).

Hi there, I’m Jason. Professionally, I write for Simple Truth. Casually, I ponder a life off the grid and poor vacation choices. If you have strong opinions on either, tweet me.