ReBOOT: Tips and Pointers for the Unexpected Midlife Job Search

As the clock struck 12 this past New Year’s Eve, so many of us joyfully celebrated the new “roaring 20’s.” As with almost every New Year, many of us tend to look at things optimistically, as a new calendar year represents a metaphorical new beginning for us all.

Ironic how similar the new 20’s were to our old 20’s already. 

This year started off bizarrely and didn’t take the foot off the pedal. In March, the world was turned upside down as COVID 19 arrived on our shores and seemingly changed life as we knew it. We cautiously avoided “big” crowds of 10 or more. Trips to the grocery store became tactically planned once a week (or longer) expeditions. Suddenly, an economy that was once flourishing is suddenly floundering with uncertainty. And for the first time in a long time, many Americans that were once comfortably employed suddenly are not. These are scary times. 

As of mid-May, unemployment in America is teetering at over 15%. Numbers have unfortunately just about doubled our 2007 – 09 recession rates. What was a steady climb for almost a decade has been nearly eradicated in one fell swoop. While some are able to claim unemployment benefits, this leaves many more still eagerly awaiting relief.

In a nutshell, this whole situation really sucks. 

In my microcosm, I remember a good friend of mine telling me a story. He was called to a giant meeting at some sort of financial firm with over 600 people. Everyone was told that they were laid off. Just like that. He was a young man at the time with great work ethic, but he was also surrounded by dozens of senior company members that were basically told, “well, figure it out.” As creatures of habit, that’s more easily said than done. 

Where do you even begin if you’re faced with these sorts of situations? Not just everyone can go back to school. Not just everyone has just themselves to think about- mouths to feed, bills to pay and whatnot. So the best we can do is dust ourselves off and go back to the drawing board. 


Let’s be real and honest here. If ever there was a time to do so, it’s now. Not everyone was 100% content with their jobs. Very few people are. If you find yourself suddenly unemployed, look at it as an opportunity. Some of us simply shine when there’s a fire lit underneath our butts. Look at this situation, as unfortunate as it is, through rosey colored glasses. Then think about what you ideally would want to pursue, and focus your efforts there.

Maybe you were a shipping clerk with dreams of lumberjacking. Or maybe a financial advisor with a side passion for art. If there’s a drastic juxtaposition in what you really desire in life, there will probably never be a better chance than now to pursue it. 

If that’s not in the cards, think about the industries that are up while everyone else is down. Tourism and certain retail outlets might be cold for a while, but healthcare, packing, production and more are suddenly on a huge upward trend. Use that knowledge to your advantage.



Seems obvious, but how many content workers do you really think have a resume ready to go? Odds are it’s something you’re going to need to work on. Format of your resume should of course be tailored to the industry that you’re seeking employment in, but with a fresh start anything is better than nothing. Think of your skills, education, training and whatnot and draft if all down. Great templates are already available in programs such as Microsoft Publisher if you’re short on time or design talent. Print copies are always great, but the real power here is going digital. Which brings us to our next point…



The world may have changed many times over since your last job hunt. For better or worse, technology is in the hub of it all. If you haven’t already done so, create a LinkedIn profile- it’s sort of like Facebook, but with more of a professional networking angle. You’d be surprised to see how many people you already might know in the real world have a great digital presence- and it’s good to have friends in high places. There’s even a job board built right into the service. 

Speaking of job boards, be sure to scout out places like, and just to mention a few. Competition is going to be tough, but that’s why it’s so important to hedge your bets and cast your line in a few different directions. Even Facebook has a new “JOBS” classified section, so applying has never been easier. New jobs are popping up every day, and HOPEFULLY more and more businesses will be opening their doors back up (with kids missing school these days, they have plenty of spare time to give you a hand with technology if need be).



While applying for jobs is as streamlined as it’s ever been, an in-person interview is STILL an in person interview. What looked great on paper might not secure you that gig when it comes to a face-to-face meeting. If you’re not the best interviewee (I’m right there with you), start with the easy stuff. Look good, smell clean, be on time. It’s hard to believe but those three things are so frequently overlooked with many job seekers. 

Most likely, you’ll be speaking from a position of experience, which is valuable! Mentally take note of your best selling points and be ready to market yourself. Aside from that, try your best to anticipate questions you might be asked, but above all, BE HONEST with your answers. It’s just as important to see if the business is right for YOU as it is for THEM. And just like the good ol’ days, ALWAYS send a thank you letter / email / card. It can’t hurt. 



When I find myself really needing motivation, I turn to books. Books, blogs and even certain social media influencers can share great motivation and inside scoops as to how to get back into “the game.” What Color is Your Parachute is such a popular advice book that it’s updated annually- they are great at keeping the relevant content current. If you’re feeling down or defeated, there are THOUSANDS of hours of uplifting motivational content for you to check out on resources like YOUTUBE. Tony Robbins, TED Talks and so much more is perfect streaming material when you’re ready to take a break from Netflix (that content has been slacking lately anyhow, IMO). 



Unfortunately, even if you secure a new job, you might not be at the level you left as far as responsibility or compensation. With the economy in shambles, I’d argue that it’s highly likely you might have to work your way back. Don’t be discouraged! As the saying goes, “opportunity is often overlooked because it disguises itself as hard work.” Stick with it long enough, and you might not only eclipse your old salary but find yourself happier than you were previously.



You’ve heard this one before. But really, really REALLY don’t be discouraged when things don’t quite go your way. The COVID crisis is uncharted waters for everyone, businesses and employees alike. History is being written as we speak. So if things don’t fall into your lap first try, don’t give up! Remember what it was like being in your early 20’s, looking for that first “real job” and all of the “no’s” that were sent your way. Use it as fuel to push yourself a little bit harder.

It’s a jungle out there, and lots of uncertainty in your future. The most important aspect of all of this is to never stop believing in yourself and to power through.