When “and” thinking goes too far

This weekend, I participated in an active learning weekend class at Harvard. We were looking at unpacking the paradoxes of leadership. We spent a significant amount of time looking at decision making processes and the difference between paradoxes (and/both) style problems and dilemmas (either/or) style problems.  To give context, an example of a paradox is work and rest. If you work too much, it’s a problem. If you rest all the time, that’s also a problem. So, it’s not work or rest, it’s both work and rest. Both of these constructs must balance. You can’t solve a paradox. Think about it, you can’t solve the need to both work and rest. Instead, one must manage the balance of both work and rest. It will take an initial decision and then regular reassessment. 

A dilemma, on the other hand, will have an either/or decision associated with it. An easy way to think of a dilemma is a moral dilemma – meaning choosing right from wrong. I can either fire someone for misconduct, or I can choose to let them stay and deal with the aftermath. However, sometimes it is more complicated than that (you might have even thought my right and wrong example is more complicated than that). You could be choosing from a right vs right scenario such as picking between 2 great candidates to hire. Or if you have the resources to only promote one person on your team and you have 2 excellent options. It could also be a wrong vs wrong scenario where there is really no great option. These situations can be tough because you do need to make a decision, and most likely some people will be unhappy with your choice, but you need to be deliberate in how you make your decision and then clearly communicate as to why you’ve made that decision. 


While in class, I had an epiphany as to one of my leadership weaknesses. Unless I feel my values are threatened, I tend to frame my dilemmas as paradoxes. Meaning, I’m trying to find an “and” solution when really, I need to make the hard choice during an “or” situation. I think that my intent behind this comes from all the conflict management training I’ve been through. When helping to mitigate conflict between individuals, it often helps to look for mutuality and one of the ways you can do this is pointing out the things you both want and need. However, if you are trying to make a tough choice and you’re too focused on trying to keep peace, you can end up with a choice that’s an average of all the options and result in a solution where no one is really happy, and you look wishy-washy as a leader. On top of that, you’ve diluted resources and must now continue to manage the outcome of your choice since a paradox requires consistent recalibration and management whereas a dilemma can allow you to drop the maintenance of the unselected choice.   


This blog is a place where I assess what led me to burnout. In many ways, my burnout blindsided me as I thought I was doing all the right things and wasn’t sure why I still hit rock bottom. As I’ve spent the last year trying to figure out how I hit burnout, this class helped me realize that too much “and” thinking (or “maximizing” as I used to call it) requires constant maintenance of your decisions and at some point, you’ll run out of capacity. In my business, I had built out so many systems and frames but many of them had been built in a way that handing off responsibility was hard. At first it was exciting, but eventually it was suffocating. The types of decisions I was largely making were ones that required consistent management after the decision and so I was subconsciously wrapping more and more obligations around myself. If I had instead made a few more “either/or” decisions up front, I could have let some of those obligations go. The hard thing is, I’m still unsure on how to assess when something is truly an "either/or” scenario or when my “and/both” superpowers would be helpful. Ironically, this in itself is a paradox.  


Confessions from a self-inflicted, overworked servant leader. 

Our teacher, Maragaret Andrews, gave us 7 questions we can use to help reframe the options and consequences of a decision. Our teacher also suggested writing things out as they can feel different when you read them as opposed to when you think or say something. So, here we go. As an exercise for myself, I’m trying to figure out my general tendencies for problem solving to see if I can gain more insight as to what led to my burnout.  

  1. What are you optimizing for? –  

    • I found that I was always optimizing for the organization or, if it was a smaller problem, I would optimize on behalf of a direct report (even if it was to my detriment). Considering servant leadership calls to me in terms of leadership styles, I do not often consider myself when thinking of a question like this. However, my body has had to stop me in my tracks to get my attention and remind me that I need to also look at optimizing my own health, well-being, and life satisfaction.  

  2. What are you trading off?  

    • If I choose to treat an either/or situation as an and/both situation, I’m choosing to trade off my energy. This only applies if the situation really is an either/or situation that I’m trying too hard to make work for everybody. I’m beginning to understand that taking from my internal resource bank without refilling it accrues health and peace of mind debts. On top of that, “Go, go, go” made “take a break” feel impossible. When I was forced to take a break, I found I didn’t know how to relax. 

  3. Who is impacted?  

    • I was so worried about adversely impacting my employees and my clients that I forgot to look at how I was impacted as well. Additionally, my choices impacted my family, which in turn impacted me in terms of shame. 

  4. How will they feel? – 

    •  I think the high of making someone else feel valuable and loved is what drives me. Many of the choices I make are because I genuinely want good things for others. However, if I was honest with those I love about just how much I was sacrificing, I think they would be unhappy with me. Apparently, I have told myself that it’s ok for me to be uncomfortable, but I don’t want anyone else to be uncomfortable. That’s not fair to either party. 

  5. What will they think? –  

    • In many ways, I may be eroding my own credibility. If I’m telling others that taking care of themselves is important, but then ignore my own self-care needs, how credible and trustworthy am I? I need to make sure that my behaviors match my values. 

  6. What do you want them to feel/think? –  

    • I want others to see someone who is imperfect but has the courage to show up anyway. I think sharing that I’m learning is one of the most powerful things I can do. I hope that it gives others permission to learn with me and I hope it gives me grace for my mistakes. I hope that this will help others to know that I’m a safe space for their imperfections to grow into strengths as well.  

  7. What are the long-term implications?  

    • We heard from the Chief Wellness Officer at Deloitte in another class and she reminded me that only you can take care of your health and wellbeing. A company would hardly wait 42 hours before reposting your job. In your family, you are not replaceable.  

    • Long term implications for my own health matter. Also, if I’m willing to stand up for my needs in a more transparent and honest way, I hope it will give more permission for others to do so too.  

  8. **Bonus question! (This was a suggestion my teacher gave just to me – especially when trying to fit a dilemma into a paradox decision) What are you afraid of happening?

    • I’ve found that I’m afraid of letting others down. I feel a strong sense of responsibility and will tie myself to things I’ve promised to do with little room for error. I tie these promises to my sense of integrity, which in most circumstances, is a good thing. However, when I refuse to renegotiate because I believe I’m going to be seen as dishonest or unreliable, that doesn’t help either. This is where my “and” thinking goes too far. I’ve somehow convinced myself that if I renegotiate, then I will be seen as unreliable. When in honesty, it should be renegotiate OR be seen as unreliable because at this point, my body won’t let me do as much as it once did and this is a much more likely outcome. 

I hope you take a chance to write out your own answers to these questions and/or save the questions for the next problem that you need to solve. I found the exercise very enlightening. To close, I love what Margaret Andrews said at the end of our class together. She said, “Leadership takes courage and courage comes from clarity.” 

If you’re interested in diving deeper into overcoming over-achiever issues, my teacher also recommended that I read The Anxious Achiever by Morra Aarons-Mele and The War of Art by Steven Pressfield. If you want to book-club it with me, let me know! 

Thanks for joining me today. I hope you find some courage through clarity today.  

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