Self-Doubt in the Job Search

I’ll let you in on a little secret. Maybe a few secrets.

I’ve owned my own business for almost thirteen years now. I’m what they call an entrepreneur. I’m living the dream.

I get to work when I want and do what I want. No, I’m not financially independent… but for many years I have not commuted and worked in an office, I haven’t had to ask for vacation leave, I have been able to stop working with people I didn’t like, and I could choose to focus on the part of my business that made the most sense at the time.

The dream.

Over the years, as I’ve toyed with the idea of having a “real job” and becoming a “productive member of society” and having all of the stableness and “security” the salary and benefits that an employer offers, I’ve had one major problem:

I didn’t know what I had to offer.

I didn’t know what skills or abilities I could bring to the table.

I didn’t even know where to start. I called a friend who is a recruiter and said “Rob, I have no idea what position I would even be suited for. Help me figure this out.”

Without hesitating he said I am clearly a product manager.  Oooooh, I like that. Product manager. It is what I’ve done for about twenty years now. I do indeed love all things product management.

So I made a product manager resume and put it out.

I’m sure of what I’ve done, and what I can do, but when I put my resume out I found that hiring managers in software companies don’t care one bit about entrepreneurs who do product management. We are square pegs, they are round holes. They look at us with pity, maybe disgust, wondering what we could possibly add to their team.

Maybe they are afraid of the entrepreneurial attitude. Maybe we are too out-of-the-box thinking for them. Maybe we are better suited for their job than for a lowly product manager role.

I’m not sure why, but the discrimination I’ve felt as a do-it-yourself, self-taught product manager was tangible.

In one interview the guy said “tell me something. Every product manager here wants to start their own side hustle, and leave their position. You have a side hustle, why would you want to come here as a product manager?” It wasn’t a regular interview question…. he was sincerely asking why in the world I would want to stop living the dream and go into corporate America. It seemed backwards to him.

Another, a VP of product, just couldn’t get past the idea that I owned JibberJobber. He was sure that I would not do my the job, but would do JibberJobber all day long while on his dime. I assured him that no, I would do the job and keep JibberJobber to my own personal time, but he just didn’t buy it. I’m not sure why.

I didn’t really know what I had to offer in the first place. And then, when I got these kinds of reactions in interviews I really wondered if I could actually do anything professionally.

I have written three books. I’ve authored 30 Pluralsight courses. I’ve created and maintained JibberJobber, which is really quite amazing. I have spoken across the U.S. and in Europe. I have an MBA and a CIS degree. I speak Spanish and English. I used to program and have lost any current skills, but I can do html-ish stuff fine. I have been general manager and sat on a (hostile) board of directors.

There’s more of course, but looking back on any of these things, how could I possibly have any doubt that I could do this job, or that job, or another job? Any of those things can be broken down into a set of skills and talents… I’m not lacking skills or talents.

But I doubt. I have thought for many years that I am unhireable. Maybe it’s because what seems to be hired is the younger, less experienced professional. “1 to 3 years experience… others need not apply.”

Am I good for anything?

In January of this year my new boss reached out his hand and brought me into a “best companies to work for” company. It was amazing. He saw me. He say my value. He valued it. And he taught me to see my value and value it.

I think that human nature is not understanding who we are and how great we are (or can be). It’s easier to see that in others, but hard to see in ourselves. Especially when the job search goes on. Especially when you get rejection after rejection. Or you continually get a third interview, but they pass on you and go with the other person. How many times can you play second chair and not get a complex about yourself?

Self-doubt is no fun. It is not productive. It puts you in a place that is not good for your networking or interviewing or just getting out of bed and continuing to fight the fight.

I don’t know how to solve your self-doubt issues. For me, I had to do stuff. I had to write another book, author another course, build more stuff in JibberJobber, get another speaking gig. I had to rack up virtual points to validate myself. Not because I needed the ego stroke, but because I needed to chip away the self-talk (and the silence in the job search, which was almost as bad), and prove that YES, I could do things. YES, I did have value. YES, I should be on your team.

It’s a hard battle, but figure out what you can do to win the battle. The alternative is that you find a way to cope, that you sink into depression, and that you go down a path that could be hard to recover from. Figuring this battle out is a life skill. It is what millennial call “adulting.”

Fight this battle because you deserve it for you. And your loved ones deserve a you that isn’t losing this battle.

I know you have value. I know you can do stuff.

Now, prove it to yourself!