How an Optimist Considers and Seeks New Work

I started a piece on Optimism, but then feeling it wouldn’t turn out well I gave up on it altogether. 

Apologies, I’m working on my dad-jokes. 

I’ve been considering optimism over the last few days. I don’t think that I publicly admit to being an optimist because some people tend to be dismissive, as though you literally don rose colored glasses. In fact, nothing can be further from the truth. I’ve always thought of myself as having a mixture of realism & idealism. In the days when AOL was the largest connector of Americans to the internet realistidealist was my screen name. What further proof can I supply?  

Optimism doesn’t mean that you have unfettered positivity in the face of all you experience. Rather, I think of it a bit like a diving board one jumps off as they prepare to go into the pool. At the very end when you are about to take a big leap it dips down in response to your weight and then springs back up to propel you forward and up. And I write this as someone with a better history of leaping in life than off board above pools. In those moments my optimism yields to altogether different emotions.   

Some people, usually those who deplete optimists, consider optimism a bottomless cup or endless well. However, we optimists have some awareness of how we are feeling and give at least fleeting thought on how to replenish ourselves when we have been drained. 

How then should you, my fellow optimist, consider pursuing new work and how? 

Is your current work draining your optimism? How much is the role you are playing depleting you and making tending to your work or yourself impossible? My friend & colleague Manjula in Hamburg responded to a recent post of mine about optimistic staff, “I try to make it clear that the person is equally valued by the team on days when that characteristic isn’t present. For the people who usually spread good cheer in the office I tell them that we totally appreciate this quality about you, but I want to assure you that this is not your job or your responsibility.” 

Are you the person on your team that has ‘morale’ expectations that are beyond what you can meet now? Do you feel comfortable creating some boundaries for yourself and the others relying on you about what is realistic? Is your boss going to back you up when you set these boundaries? (Unfortunately, most of us don’t have a manager as thoughtful as Manjula.) 

Has work been a place where you’ve been optimistic in the past? Have prior jobs been a way for you to freely express your optimism in the past in an easier way? Or did you need to keep a cap on that optimism during the workday? In all things I’m a fan of your being your truest self, but with the understanding that, as I shared above, some people might drain you, so boundaries are necessary. Nonetheless, that’s your choice. This decision about how you want it to show up during the workday may influence whether you leave where you are now or see an opportunity to make it work.

If you have become less optimistic about a future with your current employer and decide to pursue something else, how do you sustain yourself as you prepare to dive into a new pool?

• Share new expectations with those who have been most reliant on you. If/when they push past these parameters be sympathetic and firmly restate your boundaries. You may not feel at liberty to tell some of these people the particularities of your situation, but you can nonetheless get the space you need.  

• Reach out to the other optimists in your life. Tell them you may need a little more from them. No one understands better than them how others come to you and how you’ve been there in the past for them. Do your best to be specific about whether you need more check-ins, introductions, or an accountability partner.  

• Determine the criteria you want in your next workplace. It always comes down to deciding what you will prioritize next in the work you pursue from salary and schedule to colleagues and culture. Give special consideration to your emotional well-being and how your optimism was received or expected in your former workplace(s) and what you want from the next one. 

• When you are about to enter into a period of uncertainty either give yourself space and permission to explore for a set period of time, or if you know that isn’t how you work best set up specific and realistic goals that you use as your barometer of success. Celebrate when you realize those goals. Create the right environment for your optimism to thrive.

• To the extent that a work culture & boss allows you to be your best self is prioritized, ask the questions that pertain to this as you consider where to apply and in interviews. 

• Additionally, if you are an optimist considering starting-up something, please spend a bit of time reading about the pros and cons of being an optimist in those spaces and make sure you have people who provide the necessary counterweights. 

We both believe that you are about to embark on an exciting journey. Here’s to finding an even better place for your skills and perspective and a soft landing after you take your leap.  

—Russ Finkelstein is the opposite of your High School Guidance Counselor.  A career coach, social entrepreneur and advisor to founders, he is currently the Director of Coaching with the Roddenberry Fellowship, Coach-in-Residence with StartingBloc Fellowship and a Co-Founder of Title8 a Legal Marketplace. He was a founder of the noted careers website Idealist.org and his new book, "Let's Sort Out Your Career Mess, Together..." is forthcoming in 2021.