The "Shoulds" Are Slowly Killing You; And What You Can Do About It

Sep 20

Throughout all the change we experience in our lives over days, weeks, and years one thing remains constant: the self-talk inside our heads includes a lot of statements about what we should or shouldn’t do. The content and number of these “shoulds” varies over time — though some particular “shoulds” may remain with us for decades or for our entire lives.

Anytime you are telling yourself “should,” it means there is a judgment (good vs. bad, worthy vs. not worthy, moral vs. immoral) involved. Making judgments of yourself is stressful and exhausting, even when that judgment seems small. Attaching judgments to our lives clouds our brains and gets in the way of us creating what we want to create in our life or work. These judgments add up and ultimately kill our effectiveness and our happiness.

In this article I will explain how to take these stressful and unproductive shoulds and convert them to actionable plans. I’ll also give several real examples of how this works.

Three Forms of Should

Shoulds come in three major forms:

The Statement Should: “I should eat better.” “I should learn Spanish.” “I should have a conversation with my direct report about how they are underperforming.”

Statement shoulds can also just as easily take the form of “shouldn’t” such as: “I shouldn’t be looking at my phone so often.”

The Yes/No Question Should: “Should I take this job?” “Should I buy this painting for my house?” “Should I take a vacation the week before OKR finalization?” “Should I help my parents with the kitchen remodel?”

The Open-Ended Question Should: “What should a CEO be doing?” “What should I do about my team structure?” “What kind of leader should I be?” “How often should I go to the gym?”

As you read this, you may be thinking of what shoulds you have in your mind right now or what shoulds you’ve experienced this week. If you haven’t already, try bringing a should you’ve had hanging over you the past week into your mind now. As you do this, you’ll probably notice how heavy shoulds are. They make little things seem like big ones. They make important things feel absolutely dire.

If your should is formed as a question, try answering that question directly right now. If your should is a statement, see how you feel about yourself when you say to yourself what you should or shouldn’t be doing.

Stressful, right?

The good news is that there are two simple methods that reduce or even eliminate judgment of yourself while framing the problem in a way that you can actually solve. I’ll describe these two methods below along with some examples.

If/Then Method: Convert “Should” to “If/Then” Statements

The first method applies to Statement Shoulds and Yes/No Question Shoulds. Instead of asking yourself “should I do XYZ?” or saying “I should do XYZ,” turn it into the form of “If I do A, then B. If I do C, then D…” If you have one of these shoulds available to you, give it a try. Sometimes these if/then statements are simple, sometimes they are more complex and contain unknowns that you can work towards resolving as you identify them.

Example: A Rock on The Beach

I’ll give an example for me personally on a seemingly little thing that was causing stress for me at an inopportune time. I was at the beach with a friend who is also a coaching client of mine. I saw a rock I really liked and then picked it up. I asked myself, “should I take this rock home?” Once this “should” popped into my brain, my mind was filled with stressful chatter and judgments. Would taking this rock make me a rock collector now? Would I now have to collect more rocks? Wouldn’t the right thing to do be to buy a plant instead? What does it mean about me to have a rock in my house? Why do I have so much chatter in my brain about this little rock? What if someone found out I was stressing over this little rock instead of enjoying the beach? And so on. All of a sudden what was a nice day on the beach now had judgment and stress built into it.

After ruminating on this for a bit, I was fortunate that I asked my friend: “I like this rock. Should I take this rock home?” and he said “Well, if you take the rock home and you get to look at it or touch it periodically, it’ll probably bring some joy into your life. If you end up getting rid of it by throwing it away or leaving it on the side of the road, that will probably be a somewhat negative experience. And if you don’t take the rock home at all, then you’ll probably forget about the rock altogether.”

Now all the judgment and swirling in my head was gone. And I had a choice on what I could do. My friend and I reflected that it shifted my thoughts from judgments into a metaphorical game of billiards. If I hit this ball into this ball, this will happen. If I hit this other ball, that will happen. It removed the judgment and presented me with likely outcomes from options I could take.

I ended up taking the rock home and it’s sitting on my desk next to me right now.

In retrospect, it seems so obvious that the decision on what to do with the rock was blown out of proportion in my head. I use this example because it shows how even a very minor matter can be disruptive when a “should” is attached. A simple choice on whether to keep a rock all of a sudden turned into an internal courtroom trial of who I am as a person.

What’s an example of a seemingly trivial item that your brain is creating shoulds for right now? Try converting that should to “if/then” statements. And to make it even more effective, write those if/then statements down. Once you’re done with that, what has going through this process done for you?

Example: When to Transition into a Management Role

When I first joined the Airbnb engineering organization in 2014, there was a policy where each person who would eventually manage a team was required to spend a year writing code before moving into a formal management role. This policy was put in place to make sure that all managers had solid knowledge of our codebase, which would help avoid creating a management group that was out-of-touch from the work of engineers.

I joined the Airbnb software engineering infrastructure team with the intention to eventually become the manager of the team. As I integrated with the team, I realized that I was never going to be as good of an engineer as the others on the team. I also found what the team was lacking most was not an extra staff level engineer who could barely keep up; what they needed was direction, planning, and someone to help pull them out of firefighting mode.

Once I realized that, the question of “what should I do about my role?” entered my mind. As I sat with this question I found it stressful and unproductive (as all “should” questions are). It invited judgments such as what it would say about me to not spend my whole first year at the company deep in the code. Then I flipped the question to an “if/then” statement and the answer became very clear on what to do. If I were to stay as an engineer in the code, the team wouldn’t be able to scale to support the rapid growth of website traffic or the growth of the overall Airbnb engineering organization. If I started managing the team sooner, we’d have a much better chance at scaling our backend systems to support Airbnb in reaching its huge potential.

I approached our VP of Engineering with this analysis and he agreed that we should transition me into a management role early. In the 3 years following, my team grew from 15 to 150 people, we supported an engineering and data science team that grew from 120 to over 1000, and we reduced website downtime by over 10x. All of this was necessary to support a growing business that was valued at $3 billion right before I joined to become a $100 billion public company when I left 7 years later.

Goal and Plan Method: Convert “Should” to a Goal and Plan

This second method applies to all types of shoulds, though it is most relevant to open-ended question shoulds. For this method, you take whatever “should” you have been stressing over and, instead, ask yourself what goal you’d like to achieve and then put together a plan to achieve it.

Example: A CTO’s Role

A lot of Co-founder CTOs of growing startups wonder, “what should a CTO do?” or “what is a CTO supposed to do?” This question invites a lot of judgment on whether the CTO is doing the “right” thing compared to others and gets the CTO looking externally for what other CTOs are doing — when so often whatever another CTO is doing doesn’t apply to what their particular company needs at the time and their own unique skillset. Whenever this comes up with a CTO I am coaching, I always help them determine what goal they really want to achieve. This goal is usually related to making their company as successful as possible. Once we have their specific goal, then the question turns from one that includes “should” to one like “What does the company need most right now? And how can I uniquely and best contribute to that?” Answering those two questions is so much more productive and less stressful than trying to figure out the nebulous and judgment-inviting question of “what should a CTO do?”

Example: A CEO on Sales Calls

A common question that CEOs of growing SaaS/B2B startups ask themselves is, “should I be on sales calls?” When a startup is small the CEO may be the only one who can really do sales calls well. As the startup grows the CEO typically hires a salesperson or a sales leader and the demands on the CEO become larger and more varied (hiring senior executives, managing a larger internal team, etc.). This “should” question invites judgment: What does it say about me as a CEO if I am not in all the sales calls? Does that mean I am not in touch with customers? But shouldn’t a CEO be able to delegate sales calls? And so on.

If you convert the “should I be on sales calls?” question to a goal followed by a plan, then the path forward becomes much more clear and actionable. For example, the CEO might land on something like:

The most important two things for the company right now is that we put the right executive team in place to scale us long term and that we continue to close deals that help us grow in the immediate quarter. To achieve these two goals, I will set my highest personal priority to hiring a Head of Finance and VP of Engineering since these are things only I can do. I will begin to ramp down my involvement in sales calls by creating a system where our new Head of Sales ramps up quickly and has an escalation path for when my involvement would be helpful to close a large or strategic deal.

Now the CEO can begin work on that plan instead of dwelling on an unproductive “should” question.

When to Eliminate Shoulds

There are two times when you can employ either of the methods above.

In The Moment: Recognize when your brain has popped a should/shouldn’t into your consciousness. Once you’ve done that, convert that should to an If/Then Statement or a Goal and Plan. This can be done in your head or—if you’d like it to be even more effective—by writing it down.

Periodic Review: Think of all the shoulds and shouldn’ts of all types (Statement, Yes/No Question, Open-Ended Question) and write them down. Now, think of more. Once you’ve done that, ask yourself “where have I been judging myself about what I do or think?” since those are implicit shoulds. For example, “I’ve been judging myself for eating too much ice cream” is another way of saying “I should eat less ice cream.” Write those down too. Keep going. Get as many as you can. The first time you do this, you may find yourself saying “OMG I can’t believe how many shoulds I have!” Congratulate yourself for finding all of these. And then congratulate yourself for getting how far you’ve gotten in life and work with these pesky and unproductive “shoulds” clogging up your mind. Now pick one of two of these and convert them to if/then statements or a goal with a plan.

As you do this more and more, you’ll convert more shoulds into actionable steps and get better at recognizing shoulds. All of this will help you get more of what you want with less unproductive judgment and mental chatter.

Insight and Action

Answering these questions will help you become more productive and fulfilled by removing judgments and creating actionable plans:

What are the 1 or 2 biggest insights you got from this article?
What’s a little should that has been weighing on you in your life or work? Now convert that little should to either (A) if/then statements or (B) a goal and plan.
What’s a big should that has been weighing on you in your life or work? Now convert that big should to either (A) if/then statements or (B) a goal and plan.
How will you remind yourself to recognize shoulds in the moment?
What day and time every week will you review the shoulds that have been weighing you down?

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Kevin Rice