Don’t work with friends and other helpful advice you don't have to take

“Don’t get married until you’re 30”, I said knowingly to my team of precocious Gen Z do-gooders after one of them shared that she has been in a relationship for almost five years.

I regretted that pronouncement almost immediately. I had received a lot of unsolicited advice in my early 20s, and I detested how annoyingly smug older people could be when sharing their supposedly earned sagacity. 

“Everyone’s just pretending anyway, no one really knows their shit,” a friend going through an extended midlife crisis once commented. As history would repeatedly prove, experience doesn’t necessarily make a person wiser; and the perspective of a single individual, no matter how intelligent, could be quite limited.

Collective wisdom, in contrast, aggregates the knowledge and experiences of a community to form a depth of awareness and insight that is in many cases, accurate.

I’ve always believed however that collective wisdom is meant to be a guide, but not infallible. I guess the the good and bad thing about being stubborn is that I’m always questioning long-held truths, and easily enamoured by alternative routes. Divergence from common adage did not always work in my favour of course, but those that did, just like what Robert Frost discovered, has made all the difference.

1. Don’t work with friends.

My experience: You can work with friends, but set the rules and boundaries right from the very beginning.

I have been working closely with four of my best friends since 2017, through She Talks Asia. Knowing full well the power of businesses to end lifelong friendships, we played out worst case scenarios in our head and prepared for them: What if we disagree on polarizing issues? What if one of us wants to take a break? What if we don’t feel aligned anymore? Asking the hard questions forced us to answer the larger purpose of the business, and a shared vision of how it should continue to have an impact regardless of the personalities behind them.

It also helped a lot that we invested time in understanding each other’s work ethic, along with our individual strengths and weaknesses. From there, we jointly developed a clear power devolution structure that outlines our respective roles and who has a final say on things. We’re five passionate women with such strong personalities so disagreements are inevitable, but having a structure to refer to leads to a harmonious resolution.

Having boundaries also means knowing your work relationship is separate from your friendship, and making time to nurture both. I think the problem with working with friends is that the nature of your friendships suddenly devolves into something transactional. This is why there are still friendships that turn sour even if their business venture is successful. As our She Talks CEO Sarah Meier put it, “take care of each other’s energy.”

2. Don’t work in a nonprofit. You won’t be able to feed yourself.

My experience: While working in development won’t make you rich, it doesn’t have to lead to financial instability either. Choose a nonprofit that strongly believes in investing in its people. (I personally don’t trust charitable organizations that don’t pay their people a fair wage, because achieving your social mission should NEVER come at the expense of the quality of life of the people working for you.)

Nonprofit work does have its own trade-offs of course: no big mid-year bonuses, no employee loans, and a bare minimum health care plan. That being said, working in development opened up a lot of opportunities for me that my peers in another industry didn’t have as much access to: year-round scholarship and training opportunities, leadership summits, having a platform with which to try to change the world for the better, and work fulfillment that goes beyond meeting sales targets and making stockholders happy.

What I would caution young people against is believing all that thought catalog bull about dropping everything to pursue what you’re passionate about. If you have a sizeable trust fund, a viable family business you could eventually run and inherit, or just fortunately untethered from any financial responsibilities, then go ahead. Otherwise, I encourage you to pause and devise a plan before doing so. Before resigning from my job to live in Mexico as a missionary for one whole year, I looked at my finances and computed how long I could live without earning. I knew that after 12 months, I would need to immediately find work. I also gave myself a monthly budget, which meant I could only call home every two weeks for 15 minutes (Skype was still quite wonky then so I had to use prepaid long distance cards). Your plan doesn’t have to be extensive, but you at least have to know the scope, limitations, and potential consequences of your foray into the unknown.

3. Don’t take NO for an answer.

My experience: I think one of toughest pills we need to swallow about life is that there will be moments when your hard work does not lead to desired results; you can do your best and still fail. 

And that’s okay. You could choose to try again or you could choose to pursue a whole new direction. 

Unfortunately, failing at something has become synonymous with being a failure. In a world that unabashedly celebrates the comeback stories of underdogs, the grace and courage required to accept defeat have often been trivialized.

I’ve learned that the first response to rejection should be to put in the sincere effort to understand it, so that what I do after is informed by painstaking self-awareness versus a juvenile insistence on winning/being right. Persistence is an admirable quality but so is humility. There are times when NO is the appropriate and the best answer. As the serenity prayer goes: God, grant me the serenity to accept the things I cannot change, the courage to change the things I can, and the wisdom to know the difference. 

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