Life Lessons from Failure



One of our favorite Schoolin Life sayings is, “The only L’s we take are Libations,” but it’s not entirely true. Over the course of the last year, I’ve taken my fair share of L’s and quite of few of them weren’t served with a cocktail umbrella on top. We can gloss over our failures with platitudes like “a setback is only a set-up for something greater,” or, “failure is the proof that you’re trying,” but the truth is that failure is hard and it hurts. This week no one knows that more than Tiffany Haddish who the internet is all a buzz about after a video of her bombing her NYE comedy set went viral. Her jokes fell flat, no one was laughing and people were leaving the theater in droves. YIKES. Nothing feels worse than putting in the work, expecting excellence, and falling short. Often we can’t see failure in the moment. It takes reflection and introspection to really understand where we’ve faltered and what impact it might have on the rest of our lives. Now that 2018 is over, I (and Tiffany) can clearly see where we failed last year. You can listen to our recent podcast episode “Failing Fast” to catch the juicy details. Here, however, I want to dive into what I’ve learned from those failures and what I and our beloved Girls Trip star, can do to fail better (is that a thing?) in 2019. I’ve tried to spare the empty inspirational quotes and quips, but if you catch something Pinterest quote-worthy, don’t be afraid to share.


Choose spaces where failure is an option.

Your headlining tour on NYE, isn’t exactly a “safe space” for failure. Face Palm. Rigid and restrictive environments such as at work or in relationships, don’t allow innovation, flexibility, creativity, or failure. You need room to try and to fail in order to be successful. In fact, failure is not the opposite of success; it’s a part of it and it’s important that you allow room for failure. If you work or live in spaces where you’re deathly afraid to fail, work to get out, à la Jordan Peele. Seek out environments where you can try new things and survive if they don’t work out; where you can fail, and not be met with loads of shame, disappointment, anger, or abuse. Choose smaller stages to fail, sis. If you try your hand at baking what you think will be the perfect cake for your boo’s birthday, make sure you’re in a relationship where y’all can laugh about it if it ends up a #majorfail. Failure is going to happen, but it shouldn’t be fatal. Fail in supportive spaces, where your failure can be a pivot, not a painful pitfall.

Plan, develop processes, and choose the right people.

I’ve learned that most of my failures are caused by one of three things: I didn’t plan, my processes weren’t tight, or I wasn’t right for or didn’t have the right people on the job. It’s been reported that Haddish partying the night before left her unprepared to put on a killer show for NYE. I know a thing or two about being unprepared, one of my biggest failures over the last year was not appropriately planning for expenses. I often let my passions lead to the complete detriment of my pocketbook. If I want something, I go get it; plan, process, or people be damned. That mentality is great if you want to go fast, but not so great if you want to go far. You’re going to fail, but if you have a plan, your processes are tight with checks and balances in place, and you’ve got the right people on your team, any failure will be a bruise not a tattoo.

Fail fast.

Because I fail a lot, I’ve learned to do it pretty efficiently. It sounds funny, but I set goals or start projects, pilot them, and if they don’t work out, I evaluate why and then I stop doing them, ready to rebound and try something new. Sometimes I have a 30-, 90-, or 180-day process but in general, I don’t let my failures drag out. Because I know failure is inevitable, I’m always prepared to just stop doing something that isn’t working and try something else. I don’t have anything to prove and because I don’t broadcast everything I’m doing, there is no big “they will know I failed” weight over my head. Tiffany, doesn’t exactly get this same grace because of her “celebrity status” and people having their phones out at comedy shows, (speaking of which, you can do that now??), but hopefully she gets over this one quickly. You’ve got to get in and get out, fail but do it fast, don’t delay because winning is on the other side. Remember, it’s only up from there.

When was the last time you failed? What did you learn? How can Schoolin Life help you fail faster in 2019?

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