Corporate Graduation

It’s easy to show up to a new role or company and wait for them to hand you work. It’s hard to walk into an environment and shape your experience. But it’s the latter approach that’s going to generate the most rewarding outcomes — for you and the organization. This episode lays out a strategy for creating your own Rules of Engagement, including my "top 5" battle-tested rules. Weekly newsletter for Uncaging yourself: Wednesday Wisdom Show website: UncageYourself.FM *** TAKEAWAYS 1. Know yourself 2. Shape your role 3. Fixate on incentives and outcomes 4. Control high-energy zones 5. Establish bright lines *** RESOURCES Set up a discovery call for coaching with Matt Live Uncaged: try the Wednesday Wisdom newsletter Connect w/ Matt on LinkedIn Follow on Twitter @MatthewRDoan Check the show on YouTube

Work-Life Balance is BS. It's a misguided concept that leaves people with regret and untapped potential. Friend and fellow coach Paul Conley joins me to dive into this "balance" myth and other strategies that keep people from living their fullest lives. Weekly newsletter for Uncaging yourself: Wednesday Wisdom Show website: UncageYourself.FM *** TIMESTAMPS 02:34 Paul's focus 05:22 The myth of Work-Life Balance 08:51 Should we seek meaning (purpose) at work? 12:17 The (anti?) benefits of fitting in 16:14 Choosing Our Work vs. Corporate Work 20:25 Implementing "life-first" tactics 31:14 Maximizing your time on Earth  *** TAKEAWAYS 1. When you put life ahead of work, everyone else improves. 2. Seek abundance, not balance. 3. Someone else's Plan A is inevitably your Plan B. 4. Authenticity strategy: emulate, don't imitate. 5. Life hack: have fun every day. 6. You have immense control over your 9-5 experience, but people rarely implement their own designs. 7. You can feel (be) free wherever you are. The choice is yours. 8. Be (the right type of) Selfish so that you may be Selfless. 9. Stop saying, "I don't have time."  We all have the same 24 hours. Make better choices. 10. You deserve your dream life. It's not only possible; it's probable (with the right designs). *** RESOURCES Connect w/ Paul on LinkedIn Paul's Life-Work Balance Podcast Live Uncaged: try the Wednesday Wisdom newsletter Connect w/ Matt on LinkedIn Follow on Twitter @MatthewRDoan Check the show on YouTube

Creativity isn't just some abstract topic for artists. Think beyond the "in-demand skills" of today and learn how to build creative muscles that unlock a better life for you. William Willis (aka The Prolific Creator) joins us to share his transformative story (flowing between big tech and a "creator" entrepreneur), plus enlightening tips for cultivating meaning and tangible rewards inside and outside of corporate. Weekly newsletter for Uncaging yourself: try Wednesday Wisdom Show website: UncageYourself.FM  *** TIMESTAMPS 03:04 Impact of science fiction 07:22 Wrestling with a "successful" tech career 10:56 Personal learnings from experimentation 15:37 The anti-niche approach 19:42 Identifying your golden thread (EPIC) 23:45 Cultivating your scenius 32:56 Practical creativity for those feeling "caged" 37:10 How you're capping your potential 41:01 How William is methodically designing corporate re-entry 48:44 Rapid-fire questions 56:27 Every second counts *** TAKEAWAYS 1. There's immense power in unbounded experimentation (with no fixation on outcomes). 2. Be EPIC: [E]xplore interests, observe [P]atterns, [I]dentify common threads, and [C]urate creations. 3. We’re all born to create. The question is, "what are we supposed to create?" 4. Curate your environment (including people) to level up to where you want to be. 5. We become conditioned to value professional effectiveness and efficiency. 6. You're capping your potential if you're not flexing your creative "play" muscles. 7. You are an autonomous being in your world. Don't let others have you believe otherwise. 8. Don't spend your entire life building someone else's dreams (the graveyard is the wealthiest place in the world). 9. All you have is this moment. Don't settle. What can you do right now? 10. "A small, caged life is no way for a human being to live." *** RESOURCES Check out William's site: The Prolific Creator William's Substack newsletter Connect w/ William on LinkedIn Follow William on Twitter Live Uncaged: try the Wednesday Wisdom newsletter Connect w/ Matt on LinkedIn Follow on Twitter @MatthewRDoan Check the show on YouTube

What are you optimizing for? In other words, what are you trying to generate more of in your life? Most people have superficial answers. But dig deep, and you'll find what they want: some version of freedom. This episode introduces a framework for creating freedom, professionally and personally. Learn strategies and tactics for Uncaging yourself: try Wednesday Wisdom. *** TIMESTAMPS 02:41 Freedom is a feeling 04:46 Intro to Freedom Framework 05:04 Time Freedom 06:52 Financial Freedom 08:25 Relationship Freedom 10:09 Purpose Freedom 11:00 Health Freedom 11:30 Putting it all together *** TAKEAWAYS 1. Time Freedom: Conserve hours (and energy). Consciously direct those gains toward your chosen high-value activities (work and otherwise). 2. Financial Freedom: Maximize corporate utility for least effort. Diversify income streams. Systematically funnel gains toward wealth-generating assets. 3. Relationship Freedom: Graduate from “old you” relationships. Surround yourself with people and ideas that inspire, uplift, and scare you (shocking you out of your comfort zone). 4. Purpose Freedom: Cultivate “meaning” in your life in areas that resonate with you. It doesn’t have to be professional (e.g., might be parenting). Note: don’t expect corporate to deliver this for you. 5. Health Freedom: Ensure a healthy mind and body that keeps you high-functioning and energized for decades. *** RESOURCES Live Uncaged: try the Wednesday Wisdom newsletter Connect w/ Matt on LinkedIn Follow on Twitter @MatthewRDoan Check the show on YouTube Related episodes: Creating Time Freedom at Work (#38), Mastering the Bookends of Your Day (#40)

Do you believe in self-destiny? Well, then you'd better master your days. This is a practical and actionable episode focused on controlling the bookends of your day: morning and night. This is where you unlock freedom. Learn strategies and tactics for Uncaging yourself. Try Wednesday Wisdom. *** TIMESTAMPS 02:58 Why your bookends matter 04:18 Strategies for managing energy (not time) 10:51 Prioritize mornings or nights? 12:58 Morning rituals + deep work 15:03 Keeping corporate at bay 15:32 Graceful evenings 18:01 Closing your day 19:31 You can’t afford to push back *** TAKEAWAYS 1. Your bookends (AM and PM) are when you typically have the most control. 2. Early morning is the most critical time for anyone, whether you wake up at 5am or 9am. You must design your mornings with intention.  3. Outside of your 9-5, learn to do two forms of work: rituals and project-focused deep work (efforts that "move the needle" on your freedom). 4. Shutdown routines and related strategies help you compartmentalize how you spend time and ensure presence (e.g., when around family).  5. Optimize your evenings for calm, time with loved ones, next-day clarity, and excellent sleep. *** RESOURCES Live Uncaged: try the Wednesday Wisdom newsletter Connect w/ Matt on LinkedIn Follow on Twitter @MatthewRDoan Check the show on YouTube Related episodes: Creating Time Freedom at Work (#38) Suggested books (summaries): Deep Work (Cal Newport), Why We Sleep (Matthew Walker)

The universe is speaking: start your side hustle. Everyone's doing it, right? Actually, let's pause and rethink that. Not everyone should ignite this "parallel path" outside of their corporate career. Listen to this episode to help you understand if side-hustling is right for you. *** TAKEAWAYS 1. Know the difference between "investments" and "side hustles." 2. Side-hustling requires you to adopt a business owner mindset. 3. Following your passion isn't what makes a side hustle effective. 4. You'd better make sure it gives you energy. 5. Shifts in the global economy make side-hustling a "high upside, low downside" bet if you play the long game.  *** RESOURCES Live Uncaged: try the Wednesday Wisdom newsletter Connect w/ Matt on LinkedIn Follow on Twitter @MatthewRDoan Check the show on YouTube

Default thinking says, "I just need to suck it up at work." That's nonsense. You can take control of your corporate job and create Time Freedom — right where you are.   Learn the biological reasons why we feel overrun at work, plus 3 strategies (plus tactics) for creating Time Freedom. Break free of the Corporate Cage: join the Uncaged Academy. *** TIMESTAMPS 03:03 The Time Freedom mindset 03:53 That caged feeling 04:45 Why work overtakes us 07:00 How Henry Ford screwed us 09:30 Freedom framework (5 types) 10:19 Intro: 3 strategies for Time Freedom 10:36 ONE: Know thyself 12:19 TWO: Learn their game 14:57 THREE: Design your game 18:36 Recap *** TAKEAWAYS 1. You don't "find" time; you must create it. 2. Freedom is what you're born with. It's also a choice. Choose it, and then begin to manifest it. 3. Within corporate, must adopt an "outcomes over hours" mindset. 4. Understand your personal Point of Diminishing Returns at work. 5. Much of the upfront work involves identifying and confronting your limiting beliefs. *** RESOURCES Join the Uncaged Academy (cohort-based course) Subscribe to the Wednesday Wisdom newsletter Connect w/ Matt on LinkedIn Follow on Twitter @MatthewRDoan Check the show on YouTube Related episodes: Outcomes Over Hours (#35)

What path should you take? The Safe Path is predictable and comfortable. But then there's the Passion Path, where you know you'll encounter a life of adventure and excitement. This question applies equally to life and career.  Listen up to discover a mental model for approaching safety vs. passion. Break free of the Corporate Cage: join the Uncaged Academy. *** TIMESTAMPS 02:35 A question of two paths 04:28 Contemplating passion 05:39 Truly, what is safety? 07:00 Too much safety = masochism 07:22 A framework for action 11:29 Recap of big ideas *** TAKEAWAYS 1. Starting down the Safety Path gets a relevant foothold early on. But soon enough, you'll wrestle with a burning desire for passion. 2. We're never really safe if we feel continually terrible in the process. 3. Someone else's Plan A is inevitably your Plan B 4. Understand your personal Law of Diminishing Returns — the point at which it no longer makes sense to go "above and beyond" at work. 5. Use regret as a forecasting tool — think forward to your deathbed. What anticipated insights can you pull from the future to the present? *** RESOURCES Join the Uncaged Academy (cohort-based course) Subscribe to the Wednesday Wisdom newsletter Connect w/ Matt on LinkedIn Follow on Twitter @MatthewRDoan Check the show on YouTube Related episodes: Escaping the Matrix (#23)

This is a personal and emotional episode. In the months leading up to quitting corporate in March 2022, I recorded my thoughts and feelings. This episode is a compilation of those recordings — a personal journal, if you will. I discuss why I needed to make the leap, including the strategy and mindset that made it possible. I hope it helps you identify the “leaps” worth making in your life. Ready to take ownership of your career and life? I’ve got something next-level for you: the Uncaged Academy. *** TIMESTAMPS 01:35 90 DAYS out from resignation 05:58 60 DAYS out from resignation 09:14 People stuck in their Matrix 11:20 Leaving corporate as a forcing function for growth 13:55 Anticipation (visualization) of Freedom Day 14:38 30 DAYS out from resignation 15:48 Readying to lose my “guaranteed” paycheck 19:01 Feeling “alive” as I’ve cultivated my passion 21:20 7 DAYS out from resignation 24:16 Default Path vs. Pathless Path (Paul Millerd) 26:33 Resignation (Freedom) day 28:02 I resigned from corporate! *** TAKEAWAYS 1. After life fell apart for me, I took control of my corporate situation over recent years and found ways to operate on my own terms. 2. Soon, I was helping others do the same, and I discovered the seeds of a new entrepreneurial business. 3. COVID allowed me to experiment and lay the groundwork for a post-corporate life.  4. Personally, I eventually felt it wasn’t risky to leave corporate. It was riskier to stay — living a “small” life,  being undiversified, denying my burning inner purpose. 5. I realized I could model out my net worth, free time, etc. in corporate for decades ahead. That “cap” scared me. I’d rather have uncapped potential. 6. Imposterism (imposter syndrome) took hold early on as I contemplated entrepreneurial life. I had to train my mind to welcome the shift as a worthy fear. 7. Leaving the corporate “safety net” became a forcing function for me to become who I’m capable of being. 8. I had to get comfortable with not having a rigid plan or “ideal results” before taking the leap. 9. I worked with my coach to execute a strategic, well-planned exit from corporate. I wasn’t going to leave my family (including wife and 4 kids) in a tough situation. 10. With massive moves in life (e.g., buying a house, having a kid, starting a business), the timing just has to be “good enough.” It’ll never be perfect. Trust yourself.  *** RESOURCES Join the Uncaged Academy (cohort-based course) Subscribe to the Wednesday Wisdom newsletter Connect w/ Matt on LinkedIn Follow on Twitter @MatthewRDoan Check the show on YouTube Related episodes: Self-Reliance (#17), Imposter Syndrome (#30)

We're still battling remnants from the Industrial Age. One of the most notorious (and life-limiting) features is the standard workweek, including the cultural pressures to operate in a "standard" way.  Matt argues that one of the keys to time freedom is to let go of the "participation points" mentality where we show up to every meeting and take on an immense workload. The solution? Focus on outcomes, not hours.  *** TIMESTAMPS 02:23 Topical overview 03:00 Battling an antiquated belief system 05:42 Negative effects of "playing their game" 07:40 Establishing a contract (with yourself & others) 11:10 Five steps to implement "outcomes over hours" *** TAKEAWAYS 1. The traditional workweek is antiquated, and if you fall victim to its trappings, you're trading off a lot for very little in return. 2. At performance review time, no one talks about the hours you put in — they analyze the "impactful" outcomes you delivered. 3. Choosing "outcomes over hours" is a philosophy for valuing your time — being hyper-efficient with how you protect it at work while redirecting that conserved energy to your actual life priorities. 4. We must understand corporate jobs from a "utility" standpoint to maximize our income and opportunities while not senselessly going "above and beyond" because of peer pressure. 5. Identify the core outcomes you must deliver and ruthlessly adjust your calendar and habits to deliver on these.   *** RESOURCES Subscribe to the Wednesday Wisdom newsletter Connect w/ Matt on LinkedIn Follow on Twitter @MatthewRDoan Check the show on YouTube