I never have. I am routinely capable of selling myself short, I believe that this is a quality so consistent, it can also include elements of the fear of failure, spiked with Jonah Complex, with a dash of self-handicapping, and an inner critic as loud as the speakers in a car with a garish hubcaps.
But. For the majority of my adult life, I haven't had too much trouble with getting a job. When the objective of the work was something that challenged me, or I wanted to learn more about. I understood what roles disinterested me, and which energized me; I love the exchange I have with people smarter than I, so I've pursued roles with people I respect, or continuously engaged with people who are driven to explore, and who are kind. I'd like to emphasize the quality of being kind. Because no matter how curious you are, if you can't engage with others, and take them along with you on your journey, you will be lonely. Kindness begets warmth, which strengthens relationships, one of the more important elements of allowing yourself to be grateful for the life you live.
So I guess what I'm saying is, I wish I spent less time looking up jobs on static job boards, crafting ever so specific resumes and cover letters.
What would I do differently? Work at an earlier age, in different industries, Be selective of my university by only engaging with those who have coop programs, and commit to learning a skill for #100days before moving on.
I don't interview well, and I'm ok with that.