Mastering The Entrepreneur's Dilemma

This week’s newsletter is all about THE ENTREPRENEURS DILEMMA. No, I’m not talking about growth or profitability, I’m asking you to reflect on the worst advice I've ever heard, “YOU CAN HAVE IT ALL.” What a f*cking lie that is, am I right??!!



This week is all about sh*t you already know: you can’t do it all. I know what you’re thinking, “WOW SHOCKING, IF ONLY YOU HAD TOLD ME EARLIER…blah blah blah” You know you can’t do it all, I know I can’t do it all, yet here we still are…trying to do all the things. 


I say this all the time, but the question I get asked the most is, “How do you do it all?” My answer is always “I don’t.” Or, the other big question I get is, “When do you sleep?” To which my response is usually “between 10 and 11pm.” My sleep schedule is I assume fairly normal for a mom with two busy kids and a business. If I didn’t have kids, I’d probably go to sleep earlier on most days. Although, here’s the catch I actually can’t go to sleep any earlier on Mondays because I teach a nighttime yoga class. I can’t actually get to bed then because there is a physical time barrier to being able to do that. 


How often does the phrase, “I wish I could…” or “I can’t..” come up for you?


I was actually interviewing an acquaintance of mine for the research I’m doing for my Master’s program, and she went to a mastermind roundtable. The coach there told her that it wasn’t because she didn’t have enough time to do things, but that she was lazy! 


Pause, just for a moment, and picture some dude calling you “Lazy,” how does that make you feel?


I’ll tell you mine - I would want to shove his face into a wall, I mean I wouldn’t do it, most likely, but I definitely would picture it. 


But seriously, think about a time you were trying to do it all - what happened? I’ll go first… I had a full-on breakdown, and I had forgotten to pay payroll. Ya know, that very thing people rely on me for being their boss. Yes, these things happen, but like not to me, but it did. I wasn’t immune, I wasn’t under an invisibility cloak, I was smacked in the face with something real because I was so focused on all the things. 


I hadn’t just forgotten to email someone back, stood someone up for a meeting, or paid my rent check within the grace period of late; I forgot payroll. Like THE payroll. That was a huge red flag for me to get my sh*t together. I needed better boundaries and processes in place to make sure that never happens again. 


The phrase “I can’t forget payroll this week” is now a fear-based “can’t” not an actual physical/ true emotional barrier or a decision. It’s now “I can’t do that on Fridays, becauase I have to do payroll.” Because the new driving force of doing the thing is fear. 


A few years ago I read a book called Pick Three by Randi Zuckerberg. It’s all about this illusion of being able to “do it all.” If you haven’t figured out by now that there are seriously high expectations that have been placed on people like you and me from our society - LOOK OUT BELOW. And, if you have figured it out, you’re probably a lot like me and constantly wonder how you are actually going to do the things you set out to do? 


In the book Pick Three, Zuckerberg (yes, also, you probably guessed it, she is in fact Mark’s sister) creates the concept she called “The Entrepreneurs Dilemma.” When you read about this in other business books, the concept is usually tied to the dilemma of growth or profitability. That’s because you usually have to spend money to grow, which means you likely aren’t in profitability, and if you are hitting profitability you are potentially not scaling quickly.  


Zuckerberg states - The Entrepreneurs Dilemma: Maintaining friendships. Building a great company. Spending time with family. Staying fit. Getting sleep.


She says we can’t have it all, but we usually juggle three at a time. This newsletter is out on Valentine’s Day, so if you are in some sort of committed relationship, you are potentially prioritizing “family” or even “friendship.” And, since it’s Wednesday, you also probably prioritized “company time.”  Seriously though, when were you able to do all three?


We’ll discuss entrepreneurial seasons and life seasons later, and that has a huge impact on these categories. For instance, if you’re in the season of being a new mom - news flash: there will be a major lack of sleep. If you’re in the season of your kids having independence, there might be a lack of family time. There is always shifting and the scale is always tipped. 


Reflect on your past week, which did you choose? Unless you decide to open a business where you can work out with your friends that also happens to have a garage apartment for you and your family…. Just saying I doubt that’s what you’re up to though….

Real quick side note: Randi Zuckerberg isn't entirely right about the categories in my opinion. Family, Friends, Fitness, Work, and Sleep are complicated. Each family member IMO should have their own categories because my husband's needs are way different than each of my kids and even my dad's. The time I spend with them varies. Same goes for my friends. I've made a lot of friends (maybe even you reading this email) and we each spend a different amount of time together and we require different things from one another.

Fitness - some days I walk, some days I go to the gym and some days I have to cancel my habitually allotted time because it just doesn't work that day. Sleep for me is more than just rest, it's actually sleeping and it also encompasses relaxation tools and techniques, especially self-care. Where would self-care fit in on her time? 

Lastly, what Randi got wrong (once again, my opinion) is that professional work and volunteer work should not be in the same category, but normally since you can't do both at one time I get it. 

Each of these categories is complex and to put them in super basic forms like work, sleep, etc makes them feel somewhat trivial - but it does make it more digestible to see where we spend our time. So...we'll stick with her three for the basis of this email, but just know when it comes to my partner and my two kids they all don't get the same amount of time each day. Like Tuesdays, my son has a track meet that I have to miss (my husband goes,) but my daughter stays home with me and I have my graduate class. Honestly, I am not spending any time with them, but at least my daughter and I are both on our electronics together, and I have to learn to be okay with that because "work/education" was my priority that evening and sometimes that just sucks. 


Let’s take a reality inventory:

Focus on today, what categories can you confidently say you made a priority? Remember, no one is judging you for what you picked. I’m just asking you to reflect and notice because guess what you can pick all new categories tomorrow too. 

  1. Work (PS She includes all output here, even if it’s a hobby or charitable function or service.) 

  2. Family

  3. Friends

  4. Fitness

  5. Sleep


Next Two Questions:
Ask yourself: What do you WANT your priorities to be? For the two categories you COULDN’T be prioritized, ask yourself, “Why?” 

What held you back: was it an actual physical or emotional barrier or was it a barrier based on fear? What were the limitations that kept you from being able to prioritize those things? 


Remember physical and emotional barriers could look like: injuring your shoulder so you can’t go to your workout, maybe you have a friend that constantly crosses boundaries that you can’t deal with right now because you have so many other things to focus on instead, maybe you don’t have childcare to hang out with your friends, or maybe that one family member drains you when you visit your cousin. 


Fear-based “can’t” can look like ghosting that friend because you never had the conversation about how you felt, or being too scared to launch that product or service for work so never working on the finalized plans, or maybe even being too scared to try that new yoga studio because you aren’t sure if you’ll like the instructor. 


Knowing the reality of your barriers can also help you set more realistic goals in where to prioritize and realize that there will always be an imbalance in work, family, friends, fitness, and sleep…it’s all part of the entrepreneurial journey. 

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