3 Things About Job Hunting After a Career Transition That No One Will Tell You.

I’ve had a lot of different jobs over the years.

I wrote content for causes and politicians. I spent a brief stint producing a speculative oral history podcast. A few years ago, I went into the trade s— only to end up, as of last year, in technology sales.

While I was trying to find a career that felt like a fit, while juggling bills and rent payments, I often felt angry and embarrassed.

I felt like I had lots of skills to offer, but faced rejection at every turn.

I had known making a career change wouldn’t be a cakewalk. I also knew that as an older employee on the bottom rung of the career ladder, I would probably face challenges: working with people much younger than me, managing my own ego, and learning “the right way to do things.”

The working world can be a confusing and painful place.

The hardest part of my career transition was understanding the unspoken rules and credentials in an industry — whether I was bricklaying in the snow or cold-calling random people in a fancy Chicago office building.

When you start your career all over, it can be hard to understand what you need to do in order to thrive.

Particularly during the job hunt.

There are unstated powerful rules, ideas, and assumptions that guide every workplace. It’s hard to figure them out when you’re starting from scratch — especially when it’s not the first workplace you’ve ever been in.

That said, it is totally possible to overcome these obstacles, no matter who you are or what kind of stressors you’re dealing with.

Here are some of the things I wish I had known about job hunting when I first started my career transition. It would have made the whole process way less scary.

Your First Job Doesn’t Need to be Perfect.

For a long time, I was determined to get the perfect job that checked every box of my skill set.

I had management experience, design experience, and consulting experience — but all of that experience was in the nonprofit world.

And part of the reason I was making a career transition in the first place was my dissatisfaction with my previous work. I felt like I needed more training because I was constantly distracted, and depressed, and rarely was proud of my results.

But that didn’t change the fact that I was determined to get a management job — a job that reflected my equivalent experience — in whatever field I wound up in next.

Because of my parameters, my job search was fairly fruitless — I found applying for roles overwhelming, and when I lost out on interviews or didn’t get a callback, I found editing my resume or troubleshooting what went wrong hard to fix.

Eventually, one of my clients disappeared and stopped paying at a time I really needed cash. As a result, I scrambled, ultimately taking a job in entry-level sales at a company where I really liked the product and ethos.

The second I took that job, I wished I had taken an entry-level role sooner.

It is so much freaking easier to get an entry-level job at a company you want to work for, accumulating the skills and cultural knowledge you need to thrive, than it is to paper the world with your résumé for a management job.

I ultimately left that job, and I’ve heard anecdotally from HR professionals that entry-level jobs often end up being one of the more competitive roles for job hunters.

Still — there is so much to learn now in any corporate role — from software and process to overall company culture.

When you start at a lower level, there’s room for growth — you can get paid to learn things you don’t know that you don’t know.

There’s no easy entry-level role.

Though they can certainly be worth it, entry-level roles, particularly in fields that don’t require credentials, specific skills, or technical prowess are still pretty brutal.

An entry-level role is an exchange for more than money.

You trade learning things from the people around you for less autonomy and power over your day-to-day.

You often also receive more unpleasant unpalatable work that others don’t want to do.

It doesn’t matter what industry you’re in: when you have less experience and skill, you are in a different position than someone at the organization who has been that for many years.

Still: it’s often worth it to get real-world insight on what’s happening in this field.

Emotions Get In Your Way More Than You’d Think.

My job search was often stymied by frustration, jealousy, resentment, and disappointment in myself.

All those things were related to my own fear and insecurity — and those emotions also often blocked me from following faster paths, like taking jobs that were less prestigious or paid less than I thought they would.

I also never got a certification, for example, even when it would have been useful because I thought that I “should “be able to leverage my experience instead of having to take on new skills.

My path would have been faster if I had found something I was interested in, even a free course, and focused on applying myself and meeting people in that singular context.

Life got a lot easier when I was able to trust myself enough to know when the ‘easy’ or unnecessary path would save me a lot of time and strife.

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Job hunting sucks in the best circumstances. It’s particularly hard when you’re making a major career change.

Still — you really can thrive and succeed in your job hunt, even without years of experience in your field — you just have to know what you don’t know.

I wish you so much luck and health in your career journey.