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Getting your Salary Doubled and Regretting it

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Bonus: With real numbers!

Dollar bills rain down around a 90s fashion model with outstretched hands
Generated with Midjourney by the Author

In a masterstroke only fully appreciated many years later, I made a magical six-figure salary at a young age. It caused me to spend far too long thinking I was paid too much, and sticking around because of it. We’ll look at the real numbers not for points, but transparency. (Keep in mind this is from 2005–2012 or so, whatever that means economically).

Starting out

I came in the designer-door at $37,000. First job, small studio. A couple reviews and raises along the way up to 40, then $42,000. Killing it. A few years in, my largest bump to date was a clean $50,000.

And that was the last time I made a five-figure salary.

An Attempted Jump

Since college, I had always done work on the side for my friend’s startup. It wasn’t glamorous, but good and steady side-money in a growing business (like had a factory and dozens of employees business). My enterprising friend wanted to bring me on full time to shape and run the marketing and branding from within.

He offered me $65,000 to jump ship. At this point I’m 24 years old, and a 15K raise felt pretty alright. If we read between the lines here, I was also ready for something else.

So, I wrote an exquisite resignation letter, gathered my nerve and approached my boss. He didn’t accept it, which is how I learned that can even happen (respect on that move). His response — meet me for lunch this weekend and let’s chat (because as is customary, I delivered this news on a Friday afternoon).

Over decent sandwiches, his counter-offer was thus: Stick around for another year, become a Creative Director, and make $100,000. I would go from Designer to Director instantly, and have the paycheck to prove it.

The result? In short, I took the money.

I explained to my friend that his $15,000 got trumped by an additional $35,000, and thanked him for even making this outcome possible. As a bonus, I wouldn’t have to move or commute. And let’s be honest, there’s mythical status in our culture to a hundred thousand dollars fam.

What it did, though

So all good right? Ball hard. In retrospect, I treated this money as too precious for too long. Because so many levels of a typical career were ‘skipped’, it gave me the need to make up for it in some vague sense. I stayed in that job years longer than I should have, or even would have. I also bought a condo and stayed in a state and place that really wasn’t for me.

The title also gave me a false sense of accomplishment. I wouldn’t be a real Creative Director for many years. I was a good senior designer on his way, with a nice salary. There were jobs I applied to during that time that, looking back, were simply out of my league. It’s one thing to be confident, it’s another to misjudge your experience. They didn’t call me back.

It’s important to note that nothing was wrong or bad with the work or job, it was simply past time to move forward. That’s the regret, and it comes many years later.

So, what to do?

If this happens to you in some way, celebrate, then proceed with clear eyes. Take that check, more power to you. These are good problems to have. Life-changing money. But take it for the right reasons — and the right amount of time. My boss who pulled this off was even surprised when I stuck around as long as I did. (He told me this when I finally did leave).

A couple small raises came throughout the following years. $103,000, $105,000 and finally $107,500 if memory serves. The ceiling was long ago reached, I was playing catchup with myself.

The Bottom Line

Don’t let yourself get blinded or trapped by money or titles. Always be thinking about what you want out of your career. Salaries are an important factor of employment and life — but not the only one.

And remember: if this happens, you just found out rather dramatically what you’re worth.

(PRACTICAL KNOWLEDGE) is an ongoing series about presenting work, building better portfolios and being a decent creative by Andy Sheffield.

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From idea to product, one lesson at a time. To submit your story: https://tinyurl.com/bootspub1

Andy Sheffield
Andy Sheffield

Written by Andy Sheffield

 Design. Practical advice on presenting work, building better portfolios and being a decent creative. See some work: andysheffield.com

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