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On a dare from my husband: 5 Lessons Learned from Startup Life 5 years into the Crazy

Over the past five years, I’ve been part of two crazy roller coaster rides. At one, MommiesFirst, I was a founder and CEO — part of every step, every decision from the logo design and font choice to winding it down and saying goodbye. At the other, 500px, I joined 5 years into the craziness as a member of the executive team responsible for operations. MommiesFirst and 500px are two very different companies in terms of stage, sector, target market, and my own role, but despite these differences, my commitment and personal investment — the blood, tears and emotion — has been the same. Five years in the startup world is like dog years — it’s a long time to ride the roller coaster without throwing up. And with so much going on, the idea of looking back instead of charging forward seems crazy. But, recently my husband challenged me to do just that and jot down some key lessons learned at MommiesFirst and 500px, and since I’m a headstrong, Colombian woman — I always embrace a challenge.

Learn to Delegate.

Seems strange, right? Startups by necessity have lean teams, where folks are required to roll up their sleeves and do whatever it takes to get the job done. And trust me, I’m not arguing against that — but either as a leader or individual contributor you have to focus on where you are most valuable to the business and the culture of the organization. The “let’s be scrappy” or “we do it all” mentality can result in a day that lacks focus and purpose — or death by a thousand cuts — as a friend and former colleague once described. If you have the luxury of a team, then I love the management philosophy proposed by General George Patton of telling people what you need done and empowering them to get it done their way.

Take time to think. And don’t always do it alone.

Be intentional about allocating quality time to write, doodle or white board ideas, and then EXECUTE. Spending time just thinking — leads to inertia or even worse slides that are saved to some dropbox folder and never, ever seen again. And when you’re doing all this great thinking — take someone along with you for the conversation. Often times the default approach to “thinking” means getting away and working in isolation. Instead, find someone on the team you admire and together debate, banter and find solutions. One of the most insightful pieces of feedback I received most recently during an exit interview was simply in the form of a question: why does the executive team leave the office to come back with the next big strategic initiative? Instead, why aren’t you staying here and harnessing the power and ideas of the team?

Stop Being Polite. Just be Real

Anyone remember the tag line for MTV’s Real World series? Startup life is an emotional roller coaster ride and I’ve found it’s impossible to show up every day with the same smile and oozing positivity. In fact, if you do that — one day you just might erupt. It’s okay to be emotional — the work isn’t just business, it’s absolutely personal. As long as you’re not an a-hole to the team, don’t try to mask your feelings. For me, following this advice means not always being “polite”. You may not always get warm, friendly, filled with hugs Lorena. In the end, I can’t promise to be anything but real and work my hardest on behalf of the team and our goals.

Trust Yourself.

When I first joined 500px, a ton of insecurities crept into my head and heart. I mean I had never run Operations, studied law or know anything about HR rules. I Googled a lot for answers — including “how to fire someone with dignity” (seriously). In fact, the doubts I had on how to do my job well reminded me a lot of my first months, hell my first years, as a mom. I read books and blogs searching for answers — often they were contradictory and confusing. Over time, I’ve built up my confidence and learned to trust my gut. Startup life, business, operations, etc. is about the people and treating people fairly and respectfully. As long as you keep reflecting, learning and improving AND, importantly, as long as you remain true to yourself and your values, you’ll be proud of what you create — rocket ship or sinking ship!

Find Your Religion.

And I don’t mean find God — unless that’s your thing. I mean find that one thing that’s yours and yours alone — completely outside of the office. Find the escape from the emotional rollercoaster of startup life and that keeps you sane. For me it’s running. I have an amazing running buddy, who picks me up and often times waits for me because I’ve overslept after a late night up working, and we just run. We talk — rarely about work — but it is 45 minutes of pure therapy with a bit of butt kicking and a lot of sweating. I can tell when I’ve missed multiple runs — I feel disconnected and lost and in return life at work is not quite right.

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