5 Lessons I’ve Learned Jumping Careers at 40+

I’m a freelance writer.

I used to be the IT guy.

After much hemming and hawing about what to write about here, I’d like to start with some lessons I’ve learned over my first year as a freelance creative. Truthfully, many of these lessons came to light when I was still in IT, it seems that a fair bit of what I was observing was NOT, in fact, specific to IT customers. Rather, it seems these idiosyncrasies are more generally human in nature.

“The most exciting phrase to hear in science, the one that heralds new discoveries, is not, ‘Eureka! I’ve found it,’ but, ‘That’s funny!’ “

Isaac Asimov

I find this quote more and more appropriate the more I freelance.

I watch people. OK, that makes me sound creepy. What I mean is that I tend to notice things that others miss. Sitting at a coffee shop, or sitting at my desk in the front room of the IT hardware team workroom. I just didn’t give the foibles I was seeing much thought until the other day when one literally slapped me silly. I hit my inbox to find that a client I had only just started working with was putting a complete freeze on new content. Out of left field to say the least, I mean I had only just completed a site audit and presented a rough draft of an editorial calendar for their blog. I immediately flashed back to one particular day at the healthcare consulting firm I worked for in DC. There are more stories from this time. Oh yes, there are stories, and they will be posted here in due time. The short version for today is that a guy walked into my office and dumped the contents of his computer bag on my desk. Aside from the piece with a particular brand logo, there was nothing identifiably laptop-like about the pile of rubble I was looking at.

The jolting non-sequitur of these two situations almost caused a spit-take (ed note: ever tried to clean tea out of a keyboard? it’s not pretty).

You’re forgiven if it’s not as apparent, I mean a client canceling a work order and a customer with a destroyed laptop don’t sound related. At first glance. Here’s the thing—it wasn’t the details that were so striking to me.

You just never know what each day will bring

Or each minute as the case may be. That dude walking into my office with a bag full ‘o’ bits was a wake-up call. We were just finishing our Monday morning rush of “oh my god, my laptop did a thing!” visitors and I was writing up tickets for the work orders we needed to call in.

Then, suddenly, rubble.

And with the client, the request to pause all work was just as abrupt and came as just as much of a complete shock.

Clients are people. Customers are people, too, it turns out. No matter if they’re end-users within a large company, or the CEO of a 5-person startup who wants a homepage rewrite and a blog; people will be people. And that means you need to stay on your toes (and have a notebook handy to record the details after they leave your office…just saying) And just like you didn’t see the cross-over initially and I didn’t see the pile of laptop detritus coming—they’re a never-ending source of surprise.

Lesson Learned—laugh.

Non-sequiturs are funny as hell. My favorite t-shirt ever isn’t objectively funny, yet I chortle every time I even think of it. Why? because it’s just so silly.

Haikus are easy

But sometimes they don’t make sense


See? Not objectively funny, but I can guarantee at least some of you laughed. We should hang out.

It never seems to be “their” fault

That dude with the bag of detritus? He turns to me, deadpan, and says he has no idea how it happened. He swears he just went to check email on Sunday morning and BAM, there was a bag full of scrap where his laptop used to be. Amazing. Actually, at the moment I was impressed with his ability to keep a straight face. And as for the client, well shockingly enough, they were freezing work because somehow, somehow they found themselves without any cash. And despite the CEO also being the CFO nobody could seem to figure out how they came to find themselves in this situation.

Lesson Learned—Know when “go along to get along” is the right move.

With the destroyer of laptops (This person will be the star of the first chapter in what I’m calling Tales From The Help Desk, and it’s a doozy), it wasn’t my place to call him on his lies. Company policy stated that we replace broken equipment and deal with getting it fixed—it was up to his direct manager to dole out discipline. And as for the CEO, I may not want to work for someone who mishandles money like that, but that doesn’t mean I don’t want his referrals.

Mood Matters

Humans are intuitive creatures. Even those who don’t know it. We have an ability to “read” a room, doing a sort of temperature check on the folks there to see how they’re feeling. The trick is being able to pause and make use of that reading. Most of us can’t. Or don’t. This isn’t intentional, or necessarily conscious, it’s usually simply because we’re too rushed to stop and take a deep breath as we enter the meeting room. Or the coffee shop.

My desk at that healthcare place was in our front room, between the public and my team workroom (where my guys did their thing), so everyone who walked in for help had to pass right by me. Not only did this impact how I felt at any given time, but it worked in reverse. If I was consciously aware of the mood I was projecting, I could tell when it calmed down an irate customer. And if I was stressed, I could tell that amped up some folks as soon as they walked in.

Lesson Learned—Keep an even keel.

Way back in the day I was working the phones for an 800-pound software gorilla headquartered just outside of Seattle (I’ll leave you to figure out who that was). One day I took a call from an older gentleman who was…shall we say, displeased with our product and the 45 minutes he had been on hold. I never let his irate tirades affect my tone or attitude, and in the end, everything worked out for him, and me. Now, I have that sort of personality, so this may take more work for some of you, but I guarantee it will serve you well to work on not letting other people’s “stuff” affect you.

Lead quietly, even when you’re the only one in the room

This isn’t simply a volume request, it’s more of a leadership-style thing. The introverted among us (raises hand) have a unique leadership style that is often called quiet leadership (see the work of Susan Cain and Daniel Goleman among others). While we appear to be sitting quietly in the meeting, spacing out or otherwise not paying attention; we’re actually working out what we want to say in our heads before any words come out. This can lead to confusion, with bosses and coworkers seeing us as just not participating when in reality we’re formulating a response that will solve all the things in one blow. We just don’t talk through it out loud. This translates to a need for follow up. Be the person who sends the email after a meeting, summarizing the salient points you took away and offering your thoughts on how to move forward.

That client? I sent an email the day after our discussion with a summary of the work I had done, links to the product that was already paid for, and 5 ideas for how they could continue where I was leaving off. The CEO sent a lovely, apologetic message in response thanking me for being conscientious (his word). And I left the relationship secure in the knowledge that he’ll be recommending me to all his CEO buddies in the future.

Lesson Learned—Follow up matters as much as showing up in the first place.

If I had just sent an invoice for work completed and left it at that, the client may still have remembered me but there would be nothing remarkable and over time, I would fade into the background as just another partner he worked with once upon a time. By following up, I made sure I stick out in his mind. He’ll remember that I took that extra step (which took all of 3 minutes). I can’t stress this enough, follow up can mean the difference between being the person who gets the referrals and the one who’s forgotten the instant you walk out the door.

If you look for problems, They’ll likely find you

Back to that meeting and the reading you get when you walk in. If you enter the room with a sense of, “OK, who’s going to piss me off first?” I guarantee someone will oblige ASAP. The thing is, whatever that person said that set you off, probably wasn’t so bad objectively. In fact, it may have been totally innocent and it was the attitude you overlayed on the situation that actually caused the miscommunication.

When this client signed on (I don’t use full contracts all the time, I know, I know) for this project, I admit, I had a bad feeling about it. And when that customer walked into my office, the first thing on my mind was the state of what was in the bag. Now, I’m not saying that the power of my thoughts caused the laptop to shatter (that would be kinda cool though). But my mindset did absolutely color our interaction.

Lesson Learned—Trust your gut.

Then be open to what happens. If I had followed my gut 100%, I never would have worked with this CEO. Since I moved past my initial misgivings however, I made some good money and have a champion in my corner despite the seemingly negative outcome of our working relationship. I guess what I’m saying is that if you enter every working relationship skeptical of the possible outcomes you’ll just be exhausted. So don’t ignore your gut, but work with what’s in front of you and you can turn every outcome positive in at least one way.

I hope these lessons resonate with some of you. I’ll have more to say on many of these topics in the near future, so I invite you to follow along if you like life lessons, stories, or the combination thereof. Coming next week is a rundown of the reasons I made the decision to jump careers.

And if you happen to be looking for a freelance writer to help tell your story, be it personal or professional, get in touch—I’d love to help!

A version of this post originally appeared on my LinkedIn page

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