“ _I want to learn the guitar_ ,” he said. “ _But when I actually get to pick it up at the end of the day, I’m totally wiped_.” “ _So the guitar just sits there_ ,” he lamented. I hear this all the time. Ambitious professionals are holding their days together by a thread. Squeezing in a workout is a win. Skipping out early to pick up your kid is shameful. And a hobby? Well, that’s goddamn indulgent. Our “always on” work culture is quite prescriptive and performative. There’s the Monday morning meeting, 1:1s, stand-ups and the mandatory corporate trainings. As a package, this enforces a very rigid and linear day (on the left). ![Blog post image](/images/blog/Octopus-day-872x1024.jpeg)via [@davekang]() But what happens when you start living an Octopus Day? ## Are you a high-earner going through a career transition? Find purpose, navigate money scarcity and reimagine ambition with our Group Coaching program. [Apply today]() Now it takes time to move to an Octopus career. For many professionals, remote work punctured the antiquated structure of the workday. Other ways to achieve Octopus status include downshifting to a more flexible role or working for yourself. And in many cases, an Octopus career requires you to [leave money on the table.]() ## My Octopus Journey In my own life, my Octopus journey builds on the “portfolio approach” by introducing two new layers: _optionality_ and _time horizon_. ![Blog post image](/images/blog/image-1-1024x991.png) And btw, my Octopus should be read in conjunction with my personal __Success Statement:__ Here’s a breakdown of each category: __Coaching__ Coaching (both 1:1 and group) is the hands-on and deep work that I do with my clients. It’s personal, emotionally rewarding (while draining) and keeps the lights on in the Hy Household. However, I don’t want to become a full-time coach, as that would be too singular of a professional focus. __Writing a book__ This is a new addition to the list, but after writing for a decade, I finally feel called to coalesce my ideas into a weird and impactful book. You’ll be hearing a lot more about this in the months to come and this is an activity with a __long horizon__ and __delayed cash flow__. From a financial perspective, it’s [a high-optionality bet.]() __Learning AI__ I’m definitely not an _AI Hype Boi_ , but the technology has already improved my output by 20%. Which is _a lot_ for a small business owner. My biggest challenge with AI is not being able to see the range of possibilities. So I’m “forcing” myself to use it pretty much every day and to expand my use cases. Next up: building an iOS app. __Surfing and Fitness__ LA ranks #1 in the US for the _most pleasant days in the year_ – clocking in at 183. And if I’m paying [these crazy rental prices](), I am going to be outside as much as possible! ![Blog post image](/images/blog/image-2-1024x846.png) I genuinely enjoy the endorphins of [surfing](), running, hot yoga and powerlifting. Oh, and at 45 I’m in [the best shape of my life!]() __Flexibility__ One of [the biggest takeaways of middle age]() is __back problems.__ For so many friends, they all just seemed to turn on right at age 45. Given the role of physical activity in my life, I’m dedicating 15 minutes a day to stay ahead of this. __Making Music__ Yes, [I have a Soundcloud.]() Please don’t judge it, I’m a total beginner and suck at it. This has been a really interesting journey. It’s truly a hobby I’ve fantasized about for a long time. I’d be lying if I didn’t say there wasn’t [some status-seeking]() since producers like Rza, Timbaland and Metro Booming are god-like to me. I love so many different genres and it changes your perspective as a music fan. BUT, it’s INSANELY hard. Starting at 45 years old, I’ll probably never be _very good_ at it. And it’s an activity that can’t be squeezed into 15 minute increments. Just like going for a long run, I find I need 2-3 hours just to get going. Oh, and it’s [totally atelic.]() __Family and Friends__ We’re entering an inflection point in parenting. Our 10-year-old is researching sleep away camps. She can watch her younger sister. And walk to town by herself. As parents, we’re basically getting back a lot of free time. (And trust me, I haven’t forgotten the mantra _“Little kids, little problems. Big kids, big problems.”_ One of my proudest dad moments was [only being away from home]() 60 nights over the past decade. ![Blog post image](/images/blog/proudest-1024x623.jpeg) I’m excited to see how my relationship with my kids evolves as the “big problems” arise. __Deepening my spiritual practice__ This is where the juice is at. I am [a post-achievement professional]() because I believe the following: > No additional achievement can significantly move my baseline happiness. I also have hit the point of [diminishing utility of money.]() Plus, I control my free time – so I don’t even need to [use money to buy back time.]() With that said, where do you go? As you can see from the Octopus, I’m confident I’m hitting all the right external categories. Which means there’s only one place left to go – and that’s inwards. For me it’s been using [Internal Family Systems](), [meditation]() and [attachment therapy]() to better understand my low self-worth, envy, shame and constant need for validation. It’s a long meandering journey (a bit like octopus tentacles), but it’s the gateway that I just can’t ignore. And let me tell you, I’m pumped!