Ask Lots of Questions. No, seriously.

Jeremy Privett
2 min readOct 20, 2016

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This was originally sent to the folks on my newsletter.

For the past 6 months, I’ve been opening 3 days on my calendar each week to people in the Orlando Devs community to have lunch with me to talk about career advice. I’ve started to notice a pattern in the people who achieve rapid success after those lunches. They’re the people who ask lots of well thought-out questions. Not just of me, by the way, of everything and everyone.

I think people tend to avoid asking questions because they think things like:

Is this a stupid question?

Am I dumb for not knowing this already?

Will I look bad for asking this?

People have asked me a lot of questions over the years. I’ve been either a (de facto) team lead or a manager in some capacity for over 6 years now. That’s a lot of guiding people through processes and implementation. I want to be completely serious with you about something for a second:

IN THE PAST 6 YEARS, LITERALLY NOBODY HAS ASKED ME A QUESTION THAT I THOUGHT WAS STUPID.

We’re all in various stages of our career development and different skills advance at different rates. But there’s a “lifehack” you can take advantage of to advance faster than a lot of people around you:

When you reach an impasse in your progression, start asking questions.

I’m sure this has blown you away, considering the context of this post up to now, but I’m serious. Researching things on your own is important, but if you’re truly stuck, there is no shame in seeking help. Too much valuable progress is impeded by fear more than anything. We need to turn this perspective on its head.

Let’s not be afraid of helping each other or seeking help. Let’s be afraid of the alternative: If you sit there afraid of asking that question, what is the cost of the lack of forward motion? Maybe nothing in the very short-term, but if that halted progression starts to stack up? How far behind will you be in a year? Two years? Five years?

Now compare that with how much progress you stand to make in the same amount of time. I’ve met brand new graduates that seem farther along in their careers than people with several years of experience because they’re just genuinely more inquisitive than the average.

Mentorship is an important part of your growth. Seek out good mentors in the communities you’re apart of and pay the knowledge you gain forward by being a good mentor to someone else who’s coming up behind you.

Thanks for reading! If you enjoyed this, please take a second to ❤ and leave a comment letting me know your thoughts! If you want to hear more from me, join my newsletter at jeremyprivett.com.

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Jeremy Privett

Founder of Omega Vortex, Art By Ruzena, and Brawl Academy. Business consultant and coach to solopreneurs, freelancers, and small businesses.