• Kyle OConnor

Self Reflection Questionnaire & Random Musings

This blog is going to be a bit of a brain dump.

It'll be a lot of random things I've written down and some thoughts on them. But for the most part, we'll focus on a Self Reflection Exercise that I've found extremely helpful.


Much of it comes from a Tim Ferriss exercise that you can check out here. I'll add a few of my own and while I won't add my answers in full to the questions posed - I will add a few things I consider. This exercise is most helpful for business owners, self-starters and more of the sort - but there is some sort of use for nearly everyone.


While some of the questions may seem overly ambitious, that's kind of the point. They are meant to be thought starters and to promote action. Much of my brain dump information will be within the random notes section at the end of the blog.


Lets get started.


What's my 10 year plan for my business and why can't it be achieved in three years?


There isn't a second to waste. This will force you to realize what you've been putting off, what you've been too scared to put into place and what your actual goals are.


What's my 10 year plan for my business and why can't it be achieved in six months?


Now we're cooking! This will force you to ask yourself why you've been putting certain things off and if not now, when?


What are some strengths that I need to lean into?


One of the biggest problems that business owners run into is the habit of wearing all hats and not allowing themselves to do what made them successful in the first place.


For me, this is largely related to selling. I don't get to do it near as much as when I was in sales (shocking, right?) or even in the early days of Alpha Dog when that was really my only choice to fill my time.


You have a strength. Well, I have a strength. You likely have several of them. Find a way to take a block of your days and lean into them.


What might I put in place to go off the grid for a month?


This one is near and dear to me. #HustleCulture is giving a lot of young entrepreneurs the wrong idea and leading to burnout more than anything else. Yes, you obviously have to hustle and work hard to be successful. I'm not exactly breaking the news that it's not Pennys boat arriving. But I've found that balance is far more important than overextension.


I encourage employees to take a vacation every quarter. I'm going to incorporate the Bill Gates Think Week into my life starting in 2022, more on that later.


It's more than time off. While much of the Alpha Dog staff is remote, the employees that do come into the office are encouraged to arrive when they are ready to be productive and leave when they feel that productive-ness wearing thin. I'd much rather have an employee working at 75%-ish capacity for four hours than an employee at 25%-ish capacity for eight. As long as the work gets done and well, I don't really care under what circumstances it happened.


This is just the next level. At the very least, it's a good process to go through incase you are forced to go off the grid for a month. No, I'm not talking about assuming a new identity and stealing the Declaration of Independence. But it could be an illness, family matter or something else - it's good to have guardrails in place.


For me, this is keeping other options within the businesses fully briefed, capable and confident to run the show if need be. And keeping everything in my life as flexible and cloud-based as possible.


What problems can I throw money at to improve my quality of life?


This is another one that I would have scoffed at a few years ago. Throw money at something? That I don't absolutely need to?


I live by it now. Dollars come back. And if they don't, they don't. That's just how business is and you know what, it's how it will always be. But your time is non-replaceable.


Hiring was a big one. And with that delegating. I cannot overstate how much stress I have been relieved by having a talented team that I trust. This has been an investment that has paid for itself time after time.


It goes beyond the human element. We have a pretty healthy web-based app and software bill each month. Well worth it. If it comes down on time spent, headaches caused or anything of that nature - I'm all in. I'm always seeking automation.


What brings me joy? How can I increase these moments?


This one is pretty straightforward. And while it seems obvious to chase these moments, when was the last time you sat down and completely and honestly answered this question? I know I forget to do it far too often.


It doesn't have to be anything major. Or it can. For me, this tends to come back to the absence of anxiety or stress. Travel plays a major role as well. I try to do at least an extended weekend each quarter and a longer, fully unplugged vacation at least once per year. And as mentioned earlier, I'll be starting a Think Week in 2022. I know for a fact this makes me better for our clients, employees and business partners. I'm ready to attack each day I'm clocked in.


I'll keep my other answers to this question private but I can tell you that they range from small things that can occur daily to large, life-altering happenings. There are no wrong answers, as long as it brings you some joy.


What would I like less of in my life? How can I achieve this?


I'm cool with sharing three words that stuck out for me with this question - anxiety, inefficiency and duties. I've touched on all three of these so far. As for the achievement part, I focused on controlling the controllables, accepting I can't control the uncontrollables and expanding my comfort in delegation.


Also, snacks. I mean, I wouldn't like less snacks. But I should probably have less snacks.


What if I could only subtract to solve problems?


I'll admit, this is one of the Ferriss-isms that left me starting at the paper for a few minutes. Like dude, I don't even know what planet you are on right now. What does this mean?


I ended up with a few thoughts. Removing choice is going to be big for me. Whether this is what to wear, what to eat or how to spend chunks of work days - getting ahead of those decisions and having them made at go time will go a long way.


Delegation and automation will also play a big role. And subtracting unnecessary meetings and/or calls would be nice. My thought process for meetings in general all tie to the question, "Is this meeting absolutely necessary?" If it's not a resounding yes, handle it through email.


If I could only work for two hours per day, what would I do?


My answers will not make this blog, you know, trade secrets. Also, they are just really boring. But I do think it's a helpful question to ask yourself in order to streamline your efficiency and cut out the fluff that solves nothing but eating up minutes.


An employee is out to dinner with a friend and the friend asks what their boss is like. How can you make this a glowing review?


An important question for leaders to ask themselves. All too often, once people are out the door - they are the worlds problem! That obviously won't hold up for long.


I focus on a few things. Allowing employees to be heard. Encourage time off and the work/life balance, make it mandatory if you have to. Remind them of your appreciation. Remind them of the good things they have done. And perhaps most importantly, be clear and direct. Whether its in regards to duties, salary, conduct - be clear.


We have a small team within the Alpha Dog and Point Guard U walls but as the teams continue to grow, these will be the pillars I will continue to lean on.


A time traveler from 2030 arrives and tells you that your plan failed. Why?


This is my favorite one by far. You don't have to be a boss, leader, manager - nothing of that sort. This is a great question and thought exercise for anyone.


And this one takes me about as long to answer as all the other ones combined. We like to romanticize things and dream of the wealth, health and happiness. And that's good! It's what we all strive for.


This forces you to look at the other side of the coin and think about what could go wrong and if it did, how did it happen? You can sniff out obstacles before they happen, find pitfalls that you hadn't considered yet and button up where you need to.


For me, a lot of it boils down to being hesitant to be bold. When you want to rest on your laurels, that's historically the best time to pivot and expand. Or to use an even better word, explode (in a good way).


I'm also forced to think of it in the same way I consider investing, trend prediction and more. What will be the norm for the next generation? We see time and time again that businesses and individuals get caught up in now and maximizing that experience. I'm going to try and have an eye on the way the next generation will experience day to day life. A lot of answers can be found there.


Random Brain Dumps


“My social life and work life are very blended.” I saw this quote and loved it. I realize that not everyone can make this happen. But if you can, I do highly encourage it. I love Mondays and I can't imagine that would be the case if my social and work lives weren't as blended.


Think Week I mentioned it a couple times but this is something to consider, no matter your business or industry or even current season of life. Bill Gates will go somewhere remote and do nothing but read and think for a week. I'll probably do more of a Wednesday-Saturday type of thing but I'm excited to what it'll lead to. Gates credit many of his best ideas to this.

“When things are going well, people think it’s going to be springtime forever. When things are dark and stormy, they think it’s going to be wintertime forever. But I’m a student of history, and it’s always cyclical.” - Tony Robbins I love this. This is especially true of financial markets. But it could relate to your stage of life, your work life, love life, fill in the blank. I'm trying my best to stay as level as possible despite surrounding circumstances.


What is the experience of our brand? Where can we create above and beyond moments? This is my top priority for Alpha Dog and Point Guard U throughout the rest of the year. Experiences are what resonate and we need to do better at creating them, whether it's through customer service, relationships or whatever else. Creating those above and beyond moments stick with people and blossom word of mouth referrals, client loyalty and overall satisfaction.


Crypto & Top Shot This is not financial advice. But the last week-ish has been a good time to dip your toe into crypto. My largest position is in BTC (Bitcoin) but ETH (Ethereum) is gaining. For those of you that want to have a little more fun, Dogecoin is coming to Coinbase soon.


Speaking of ETH, it's also a good time to hop on Top Shot during this bear market. Again, not financial advice. There are plenty of people looking to flip and make money after a massive bull run a couple months ago but I can't get enough of the collecting aspect. The moments are so cool and the community surrounding Top Shot is fantastic. I'm slowly building out my Ja Morant collection.


Turn & Learn I heard this awhile back from Brene Brown. This is where your team writes down answers on a piece of paper and everyone flips at the same time. It avoid the Halo Effect, where the most influential person will dictate the answers of others. It also avoids the Bandwagon Effect. I'm trying to incorporate this as much as possible moving forward.


“We don’t see things as they are. We see them as we are.” - Anais Nin I just like this quote. I've been doing my best to see things as people with different backgrounds and/or situations as me may see them.