My most useful career experience was about eight years ago when I was trying to break into the world of VC-backed startups. I applied to hundreds of jobs: low-level VC roles, startups jobs, even to big tech companies. I got rejected from every single one. Big companies rejected me outright or gave me a courtesy interview before rejecting me. VCs told me they wanted someone with VC experience. Startups at the time were laying people off. The economy was bad (particularly where I was looking – consumer internet) and I had a strange resume (computer programmer, small bootstrapped startups, undergrad and masters studying Philosophy/mathematical logic).
The reason this period was so useful was that it helped me develop a really thick skin. I came to realize that employers weren’t really rejecting me as a person or on my potential – they were rejecting a resume. As it became depersonalized, I became bolder in my tactics. I eventually landed a job at Bessemer (thanks to their willingness to take chances and look beyond resumes), which led to getting my first VC-backed startup funded, and things got better from there.
One of the great things about looking for a job is that your “payoff” is almost always a max function (the best of all attempts), not an average. This is also generally true for raising VC financing, doing bizdev partnerships, hiring programmers, finding good advisors/mentors, even blogging and marketing. I probably got rejected by someone once a day last week alone. In one case a friend who tried to help called me to console me. He seemed surprised when I told him: “no worries – this is a daily occurrence – we’ll just keep trying.” If you aren’t getting rejected on a daily basis, your goals aren’t ambitious enough.