One Word Entrepreneurs must Avoid

January 26, 2018


If you notice the title of this post, one thing might be apparent, I chose to use the word "must" instead of the word "should".  




First, because "must" connotes a sense of importance and urgency whereas "should" sounds much more, mild, meak and less urgent.  Second, because I hate the word "should."  As a matter of fact, I hate it with a passion.  "Hate" is a very strong word and I reserve it for things that are truly deserving.  But words matter.  Our choice of words affects not only how we feel but also how others perceive us.  


One of my favorite podcasts lately is Tim Ferris' "Tribe of Mentors".  In one of his podcasts he interviews a former navy seal, famous author and one of the most decorated navy seals of the Iraq war: Jocko Willink.  During the interview Tim asks Jocko a question which he asks every one of the 130 famous people he interviews in Tribe of Mentors: "If you could put anything on a billboard what would it be?" Jocko's answer is: "Freedom = Discipline."  This seems counter-intuitive until Jocko explains that when you're disciplined about working out you lose weight and stay physically fit.  When your disciplined about financial planning and management, you increase the value of your assets and financial well being.  When you're disciplined about product management in your startup, you build great products and ship them on time.  When you're disciplined about hiring people that are true to your startups mission and values, you preserve the culture of your company and make it stronger.  


That's why I hate the word "should."  Think about your own situation as a founder or startup builder for a minute.  How many of these situations actually ring true?


- I should really follow up with that client and find out why he's not signing the contract


- I should talk to this product manager and understand why he's not able to work with the engineering team


- I should work on my pitch given the feedback from the last VC's I saw


- I should spend more time with my wife given the hours I've been putting in at work


- I should get in an hour in at the gym with all the stress I have


- I should get more sleep.  I've worked until 3am the past 5 days in a row


- I should tell my co-founder we're running out of money (usually followed by violent twitches, deep sighs, tears, the smashing of a laptop or all of the above)


I bet most of you reading these statements have made them at some point.  Now answer these questions:


1.  How did thinking or uttering those statements make you feeling emotionally?


2.  Did you immediately take decisive action on these things?  If you did, how did that make you feel?  If you didn't and uttered the same sentence 1 week, 1 month or 3 months later, how did you feel?


Do you see a pattern emerging?  I did and that's why I grew to hate the word "should."  That's also why I chose to make a superhuman effort to ban it from the words I use; even subconsciously.  


In his book, Awaken the Giant Within, Super-Coach Tony Robbins talks about how we can create powerful lives.  One of the things he mentions, which I believe in with a passion, is the need to simply make decisions.  Making decisions liberates, gives us purpose and gives us focus.  This is especially true as entrepreneurs.  Often I find that I'm stressed out because I need to make a decision on something important that I haven't quite decided on.  The longer I take to make the decision, the more stressed out I get.  Once I make the decision, for better or for worse, I feel liberated and I move into execution mode.  That's key since execution and a penchant for action is one of the things that makes the difference between success and failure in startup land. (Tweet this)  


That's another reason I hate the word "should."  "Should" means indecision.  It means I need to do something but I'm not going to.  I'm going to think it through.  I'm going to delay.  I'm going to kick the can down the road.  I'm going to drift in indecision. 

For example, one of the clients I coach was talking the other day about how he realizes he spends too much time working and worrying about his work situation (he works in a startup).  He recognized that the amount of time spent at work or worrying about work was seriously affecting his ability to engage with other things that mattered to him: Time with his partner.  The quality and strength of his friendships.  And even the amount time he spent engaging in other activities such as reading or being outdoors.  When I asked him how he might spend time re-engaging with friends or pursuing an activity that would be rewarding he replied:  "Well, I really enjoy reading.  I suppose I could set up a monthly book club with friends where we could read an interesting book and discuss it over coffee.  That would help me see my friends more often and get my mind off work.  I should really do that."  There was "that" word again.  So I pressed on:  "It feels like spending time with friends and reading really matters to you.  What's stopping you from starting this book club right now?"

As we talked more about the idea, the more he grew excited.  By the end of the conversation he made the decision to do the book club before our next meeting.  His demeanor totally changed.  He felt happy, exhilarated and relieved.  Two days ago he sent me the excel list and google form for the people he had sent the invitations out to.  He moved from "should" to "will".  He moved from uncertainty to certainty and from indecision to action.  More importantly, the more we accomplish the things we need to do, the more we strengthen that muscle to take on even more challenges. 


How to remove "Should" from our vocabularies


For starters I'm not saying you should remove the word "should" from your vocabulary entirely (no pun intended).  It exists in the English language for a reason and there will be times when you feel it's really the most appropriate word to use, particularly when your talking to someone else and trying to provide help or advice.  Where it hurts us founders is when it delays or paralyzes our decision-making or when it reinforces a particular pattern of behavior that we're trying to change.  


Here are some tips for how I handle my "should" situations when they pop up  - particularly when it comes to my business, my kids and my close relationships.  


1.  As soon as the word pops into my head or comes out I try to classify the action / decision as  "must do now, must to by x date or simply won't do."  If it's one of the first two, it's goes into Asana or my Calendar (depending on the nature of the task) as a task with a date behind it.  If not, I just let it go.


2.  I think to myself "what are the consequences of not doing this either immediately or in the near future"? Depending on the severity of the consequences, the item in question goes into my task list or gets discarded.


3.  If it's something rather important, I might also ask myself "How will I feel once I get this done?" or "How will I feel if I don't get this done?"  My feelings are important.  If I know ignoring this task is going to make me feel guilty or is going to further guilt I already have, it goes in the task list with a realistic date behind it.  A realistic date matters or the item simply becomes something you "should" have done if you miss it. 


4.  Depending on how important the item is or if it involves one or more other parties, I'll also ask myself whether delaying or not doing the task hurts my integrity.  Having integrity with yourself and others is one of the first things my own coach taught me and although I still have occasional struggles, I'm usually true to my word.  If I tell someone I'm going to do something I do it.  If I'm late, I'll reach out and acknowledge that and see if I can agree with the other party to a new due date for the item in question.  


5.  I've learned to simply say "no."  Every one of us strives to be successful. The problem is the more successful you become, the more you need to learn to say "no."  (Tweet this).  There are simply too many things on your plate and prioritizing and executing becomes essential to continued success.  I used to accept most meetings people asked when they reached out to meet for coffee.  Now, I'm much more selective given my priorities.  I'd rather be honest up front and save of us both the time.  It also helps me stay focused on what I need to be doing (as opposed to what I "should" be doing).


6.  Lastly, I practice changing the nature of the sentence in question in my head and swap out the word "should" for "will do" or "must do" and see how I feel.  Strangely, especially if the item is really important, the second I say "I'm going to do X or Y", I usually feel a small surge of energy and enthusiasm.  It actually helps me get that item done.


"Should" is a very dangerous word because it can leave us in no man's land.  When we use it with others, the degree of seriousness of what we might be requesting can also be put in doubt.  Today, for example, I was having lunch with a good friend of mine, Sachit Kamat, an ex-Linkedin executive who is co-founder and CEO at Zently.  As a former product manager who worked closely with engineers,  he had this to say:


“I never use that word [should] with engineers because it creates the space to build something that wasn’t intended.” (Tweet this)


So, in closing, the situation and type of audience you might be talking to is also key here.  If you need to get something done or want someone else to do something important, "should" is not your friend.  "Should" = Ambiguity and ambiguity is a founder's enemy. (Tweet this)


Now you really "should" get back to work building your startup,


So that's it for me folks.  I hope this post has been useful.  If it's been helpful please like, share and comment below. 


Also remember that mad mork stories is now on audio so check out my podcasts. 


If you're a senior marketing executive and feel like you might benefit from some coaching, feel free to book a session here (first session is complimentary) or visit my Facebook page for more info. 


Mad Mork

The Storyteller






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