Anchors Aweigh! Sometimes the riskiest bet is playing it safe.

by Jennifer Alice Jackson, May 24, 2017

Last week I was enjoying an Honest Tea (my sugar splurge when I don’t feel like drinking plain water) and found this quote under the bottle cap: “A ship in harbor is safe, but that is not what ships are built for.” – John A. Shedd.

Nautical sidebar for land lovers like myself: Generally speaking, harbors are safe places for ships. But when a hurricane or major storm comes, the harbor becomes a stationary battering ram that ships are tossed against by huge waves. When the storm comes – the best bet for survival is to head for open sea and outrun the storm. But if you’re caught in the storm, you steer the ship to take the waves head-on because that’s what ships are designed to do. They’re meant to slice through the water under their own power, not be knocked about by wind and wave like a piece of driftwood.

Now back to the bottle cap and why it resonated with me. When you spend the first half of your life in hard core overachiever mode, running plays that were designed long before you were born (good grades, good schools, good job…good life), there comes a time of reckoning.   A time when you re-evaluate your life’s trajectory and question if it’s what you want. Really want. Like wish on a star/blow out the birthday candles/throw a penny in the fountain want. If you find yourself staring into your future, not smiling, but grimacing with feelings of dread or despair – staying the course is not an option. Even if the course entails the good job, good check and good life you’ve worked really hard to obtain.

So I tested the waters by telling my inner circle of family and friends that I, MIT graduate in the high-potential program at one of the Big Three car companies, really wanted to run a professional dance company. The most common response was some version of 1) <<sound of crickets>>, 2) cocked-head stare of a confused puppy, then 3) “are you out of your %$#& mind?!?!” Now I know these reactions came from a place of love, of wanting me to be safe and stable as an engineer. Wanting me to be a ship in harbor, anchored by benefits, vacation time and a safe, predictable future.

Thankfully there were a few whose reactions were more along the line of <<giant grin with twinkling eyes>> “that’s perfect for you!” This precious inner circle was encouraging me to be a fully actualized, gloriously in motion, ship at sea. I’m proud to say that I took a chance to be what I was built for, and have been embracing new goals ever since. Anchors aweigh!

So are there areas in your life where you’re playing it safe but you know in your gut that’s the wrong move? Are you floating along like driftwood instead of setting your own direction? My example revolves around career, but these situations can be in any aspect of your life that requires you stand for yourself and what you need.

Do you see yourself in any of these scenarios? You have a friend you’d like to ask out on a date, but instead you wonder “what if” while you eat dinner alone. There’s a new dance class or sport you think you’d love, but you tell yourself you’re too heavy/not good enough yet – so you go home, turn on the TV and eat a donut. Are you holding your tongue about something that really bothers you instead of having a difficult conversation to broker a solution? If so, your ship is stuck in the harbor of doubt and fear.

The world needs you to be you – fully, unabashedly, brilliantly you. Every time you deny your gifts, your intuition, your desire to be your best – you diminish the impact you can have on the world and become a little bit more mediocre.

The world won’t end if you opt to maintain the status quo instead of taking a chance on yourself every now and again. But if that’s your only course of action – if you always stay in the harbor when the sea calls – you are living small and curating a life of regret. So please go try. And occasionally fail. And try again until you’re satisfied you’re living your life, the best way you can. That’s what you were built for.


Jennifer Alice Jackson, the Career Pivot CatalystTM, is an artsy nerd, entrepreneur and a master at making career pivots. My 25+ year non-linear career spans engineering, management consulting, arts management, diversity and entrepreneurship. I provide guidance to professionals who are ready to change careers but don’t know their answer to “what next?” I also coach clients to efficiently navigate the personal, professional and financial hurdles that stand in the way of realizing their new career goals. If you’d like to join my tribe of career changers, add yourself to my mailing list.