30 Life Decisions and Systems
Curate your systems and plans
Random Observation/Comment #866: I chose the path of perfect simplicity.
//Our happiness jar moments from 2024
Why this List?
Over the years, I’ve realized the little choices you barely notice, like whether you’ll invest in a decent desk chair or uninstalling that mobile game your wife hates, are much more important than you think.
This list started as a number of decisions I made that would have made me a completely person with a different routine with these pivotal forks in the road. It wound up being a look into the meta decisions we make on my habits and interests that have shaped my systems, routines, and therefore how I spend my time. This was certainly a fun and enlightening one to write.
Choosing a Spouse or Life Partner - This is your anchor relationship; pick someone who supports your growth. Love and passion is important, but also look at shared values, ambition, and mutual respect to make life’s journey smoother. It also helps if your life partner is also a great cleanly roommate.
Having or Not Having Children - Kids are both an immeasurable joy and a lifelong responsibility. Weigh your timing (it’s never going to be a perfect time), financial readiness (you’re absolutely under budgeting), and the emotional bandwidth you can commit. 9/10 would do it again knowing the journey at the sacrifice of my hair and money. The 1/10 would likely have seen way too much travel and some freak helicopter accident.
Defining Your Core Career Path - Whether you’re climbing the corporate ladder or launching a business, the key is alignment with what you love to do. Career shapes so much of your identity and daily life. It’s who you’re spending time with and how you’re spending your time devoted to a life cause. Damn, that’s a lot of pressure. 10/10 would choose a high paying job that can be done by Clembot, so you can focus on the fun artistic things without worrying about a paycheck.
Deciding Where to Live - A location that resonates with your priorities. This is the community, pace, climate and it creates a sense of belonging. Carefully balance proximity to work with your desire for a certain lifestyle. We totally lucked out changing cities from Brooklyn to suburban Denver when we did. I think being awesome people will make the place you live awesome.
Buying or Renting a Home - Ownership has pride and financial upside, but renting offers freedom. We evaluated job stability, the real estate market, and personal goals. Being homeowners is really rewarding and also a lot more work than I thought in the beginning.
Choosing a Car or Transportation Method - A car can be a statement of style, comfort, and/or necessity. We were car-free for so long that we needed to adjust our workouts in Denver to replace the amount of walking we did back in NYC. This might be a moot point if we get autonomous taxis. C’mon, tech billionaires. Make it so.
Investing in Health Routines - Your daily habits (e.g. exercise, nutrition, sleep) are those slow-burn choices that define your future vitality. Small, consistent steps often beat dramatic but unsustainable changes. Yes, we’re doing dry January (or at least a sober curious dry-ish January), but wouldn’t it be better if we just reduce the intake of toxins that distract us from reality?
Selecting Your Social Circle - Friends shape your perspective. Seek people who challenge you to improve, but also allow you to be yourself. This balance of support and honesty helps you grow. You’re also the curator of this circle. Be the active leader to host parties and attend fun events. The Northend beefcakes are crushing it.
Building a System for Continuous Learning (and tinkering) - Formal education aside, staying curious with books, podcasts, online courses, or mentors keeps you relevant and energized. I’ve found that the Bachelor and Master’s program I attended was just scratching the surface of the obsessions I dove into afterwards. Constantly staying curious and taking the opportunities in front of me is because of this system of tinkering.
Choosing Hobbies and Passions - Hobbies restore creativity and keep you balanced. Whether it’s music, painting, table tennis, disc golf or coding projects - explore and commit to at least one outside-your-job passion. It helps if that activity also gets you outside and keeps you active.
Investing in Quality Tools - From a reliable laptop to a solid set of kitchen knives, the right tools optimize time and reduce frustration. Over years, investing in durability pays off. I will likely get the better microphone, speaker, water bottle, camera, smart phone, etc. because it’ll last me longer. I will also likely buy that $20 AI subscription if I can figure out how it can improve my daily flow. This was the most fun way of spending my winter vacation.
Managing Personal Finances - Budgeting, saving, and investing aren’t just about numbers; they’re about peace of mind. Set financial goals to give yourself wiggle room for bigger life moves. Be sure to learn the basics of finance because rich people are not using their salaries to become wealthy - they’re using their investments and compound interest.
Establishing a Morning/Nighttime Routine - Whether it’s journaling, stretching, or reading, a consistent morning routine sets your day’s tone and fosters a sense of control.
Choosing Mentors or Role Models - Identify people whose insights guide your growth. These can be peers or people at the top of their industry (maybe even your parents). They are the folks who steer you through both inspiration and practical advice. More important than having a mentor is keeping them up-to-date with your life choices and milestones.
Practicing Emotional Regulation - How you manage anger, anxiety, or sadness determines your resilience. Choose methods like meditation, therapy, or consistent reflection to be a part of your normal routine. I think this was a part of my life that was fairly stoic and needed some color to feel the emotional ranges. I also think dealing with this independently is different from dealing with this as a couple.
Pursuing a Side Project or Small Business - Side projects can offer secondary income, creative fulfillment, and new skills. They can also future-proof you against economic shifts. Most successful millionaires have more than 5 streams of income. It’s important to diversify and also figure out what area truly brings you joy. For me, it’s building a useful app and maybe figuring out how to create a disc golf course near my house. For you, it might be something related to your hobbies and passions. Wouldn’t it be cool if you could look at the articles you read, videos/shorts recommended, and podcasts you listen to in order to get a printout of your ideal side project? Time to build it for boomers.
Designing Your Workspace - A space that energizes rather than drains you can dramatically improve focus. Consider ergonomics, lighting, and personal touches. I personally have also created habits that might be specific to certain devices. I love writing on a keyboard with my laptop setup, but I might also find more productivity if I get into the zone while on my phone. Perhaps this is also cutting down the distractions in your workspace so you’re not tempted to play a round of VR table tennis when something hard comes up. Hold, please.
Investing in Self-Care and Relaxation - You can’t pour from an empty cup. Scheduling time for spa days, nature walks, or creative pursuits can prevent burnout. Also, get an awesome antigravity massage chair in your basement so you can use it after lunch for a short nap. Works every time.
Choosing How to Give Back - Philanthropy, volunteering, or simply helping a neighbor fosters empathy and a sense of purpose. Find causes that resonate with your values. This is another underinvested area for most people (including myself). I do think giving back is important, but we just want to do it with highest impact. Is it the dollar donation for a homeless person or a hamburger?
Deciding on Your Online Presence - Social media can open doors or become a source of stress. Manage your digital footprint by organizing your relationship with it. Be deliberate in what you share and how you want to engage. I personally love taking photos and making AI artwork because it helps me record my life. It’s interesting how much of my time is devoted to capturing the moment for my future enjoyment. I don’t get rid of that photography eye.
Developing Communication Skills - Learn the art of active listening and clear expression. This single shift can upgrade personal relationships and professional influence. Public speaking might be one of these as well. I think the biggest arbitrage to AI advancement is in-person physical communication. AI won’t be able to make me cry, right?
Building Conflict Resolution Strategies - Whether at work or with loved ones, healthy confrontation can save relationships. Learn to disagree respectfully while preserving trust. This is a skill that is learned by many husbands to diffuse fights. She has longer heels and their dug into more stable ground.
Curating Your Daily Consumption (Media & News) - The content you consume shapes your mindset. Be selective and avoid mental clutter—quality over quantity. Don’t get stuck in your echo chamber and be sure to have an open mind to the incentives behind each article.
Staying Organized with Systems - Organization isn’t just cleanliness; it’s mental clarity. Simple to-do lists, time-blocking, or workflow apps keep you from feeling overwhelmed. I do love a list. It has helped me with a lot of coordination.
Mapping Your Personal Philosophy - Define what “success” and “meaning” look like to you. Reflecting on life principle (e.g. kindness or curiosity) helps you navigate tough decisions. I think this reflection is also an under investment as the decisions you make on this philosophy of values should guide you with the harder decisions.
Planning for Emergencies - Have a buffer fund, insurance, and even contingency plans for career setbacks or natural disasters. Peace of mind grows with preparation. I’m not a prepper, but I like being prepared.
Approaching Marriage or Life Milestones with Intention - Ceremonies like weddings or milestone birthdays can be transformative or superficial. Decide which traditions resonate and make them genuinely yours. I love having parties coinciding with holidays to look forward to each month.
Setting Boundaries - With family, friends, or colleagues, it’s crucial to protect your time and emotional well-being. Boundaries aren’t selfish— they foster respect. These boundaries are even more important for guiding your child.
Deciding When to Reinvent Yourself - Over time, your interests and priorities shift. People change. Embracing personal reinvention (e.g. switching careers, mastering a new skill, joining new communities) can keep you inspired and evolving. It can also be very scary. Dip your toe in or throw yourself in the deep end. Either way, be kind to yourself while you’re on this journey.
Narrow down your creative outlet - Mine just so happens to be writing lists of 30. It’s the best I could do for myself in research, understanding, and self-reflection. It might not be for you, but you’ll need to find the thing that helps you get through your stress.
~See Lemons Make Important Decisions