Career Transition Advice and Resources

For friends entering the workforce for the first time, recently laid off, in a job searching for more purpose/meaning, or on sabbatical evaluating the options out there, here is a list of links, quotes, ideas and other useful resources I’ve found helpful in navigating career and job transitions:

  • The concept of Ikigai is a useful lens to use in thinking about your optimal contribution:

Bull’s eye represents the role you were born for ^^

  • Careers and jobs meet different needs that we all have: income, safety, joy, camaraderie, autonomy mastery purpose, recognition, etc. You can visualize these as a radar chart - the goal is to learn what your need profile looks like then do the work that maximally meets those needs.

  • Your job doesn’t need to fill these needs on its own. You can/should supplement the delta of where the job fails to meet the needs with external sources.

  • Schools inherently don’t do a good job of “divergent before convergent” thinking in helping us gain exposure to all the possibilities - we get funneled down a career path based on early (sometimes arbitrary) choices that can lead us astray to a local maxima. The way to identify when this has happened is through Parallax, or getting different angles on the same thing.

  • I’m biased but our events are fantastic melting pots of diversity with people of all different backgrounds, experiences, roles, skill sets, nationalities, etc and a great way to step back and gain a new professional vantage point. Startup Weekends are also great for this and can be found in most major cities.

  • Simon Sinek’s “Start With Why” methodology is probably the single most-useful exercise I’ve gone through in terms understanding my own purpose, strengths, curiosity, etc. Watch his famous TED Talk first if you haven’t seen it. If that resonates, consider doing his online “Find your Why” academy. If that’s too pricey ($250) you can get the gist of the ideas therein from his book but I found the self-guided online program to be far superior to the book. This is my why and output from the Part III of his program. I’ve played the partner role for a number of friends now through that program and across the board friends have found it valuable in gaining understanding of their why.

  • Strengths Finder is a useful tool. They have an online assessment you can go through. It’s another way of unearthing what your core strengths are (different than your WHY) and it helps provide another useful angle on seeing things. Human design, DiSC, Kolbe A Index are other lenses that provide different vantage points.

  • Paul Graham is founder of the Y Combinator incubator and a personal hero. He has written a number of wonderful essays that are all worth reading but the best three most helpful for this situation are:

  • My friend Marisa Meddin is a “clarity advisor” with a knack for helping people in transition figure out their next move. I interviewed her on Nomad Podcast here and she talked about how, with a suboptimal environment, she hacked her mentor situation by surrounding herself with “virtual mentors” via podcasts. Don’t let your immediate social circle dictate your future trajectory. As my friend Matt likes to say, “It’s incumbent upon you to pump that juice into your dome on a daily basis.” ← “juice” being the wisdom and ideas from people who inspire you. If you don’t have them physically around you it’s your responsibility to create the virtual advisory board you need.

  • Getting inspired is important because it’s the emotional fuel you put into your tank and you need to periodically “top-up” because overcoming the inertia of changing your situation takes emotional fuel. There are a sea of inspiring talks out there - I’ve found these particularly good:

Commencement addresses are high-yield sources of inspiration (and it makes sense if you consider that they’re these impossibly dense distillations of life wisdom for new graduates). Life hack: make a “watch later” list in your YouTube and queue these up when you have downtime.

  • If you have the luxury of a sabbatical to figure things out 80,000 hours has a career guide and a whole process to determine your highest and best use as a human. They’re heavy on Effective Altruism which IMO is culty and overboard but their fundamental approach and framework for the problem of finding your ideal role is sound and you don’t have to subscribe to an ideology to extract valuable ideas from it.

Other random thoughts:

  • Cory Miller of iThemes once said it’s no more complicated than this:

Do something you enjoy, for people you like, with people you love.

I was on the fence at one point having been in a floundering consulting career and was in a quandary fretting whether I could ever go back to being an employee again going to work for my friend Josh at Pagely. That quote from Cory though kept popping in my head and eventually tipped the scales and gave me the permission to try it and renouncing my ego and taking that plunge was arguably the best decision I ever made professionally. I wrote up my thoughts on my career transition when I started at Pagely here and when I left here.

  • This is key: to the extent you can reduce personal burn rate, then you need less income to offset expenses to remain cash neutral. Once you achieve buoyancy of being cash neutral on passive income while you sleep, then you have true freedom. You can then take a job on better terms and know you don’t need it (negotiating leverage) or you can spend your energy to amplify your business but either way it’s purely an optimization choice instead of a forced move.
  • Starting a side hustle that produces passive income should be a goal even if you have a FT job you love. This is the ultimate insurance policy: safety, diversification of income and peace of mind. There are a bazillion courses that propose to teach you how to start a side biz but the best, most deterministic formula I have seen so far for creating a small product that you know will sell on day one is Stacking the Bricks. It’s a playbook that works and you can do it while working a FT job plus they have a great supportive community of others in the same boat so you aren’t doing it alone.
  • A good book on this concept of ascending from employee → consultant → biz owner → investor = Robert Kiyosaki’s “Rich Dad Poor Dad." His online game Cashflow is good for drilling the principles and you can find local groups on Meetup that play it as a board game in person (which is a more social fun way to learn it). The other de facto resource on this topic Is arguably 4 Hour Workweek by Tim Ferris (also a good podcast). Probably 80% of all the guests I interviewed on Nomad Podcast cited that as their single, most-formative book in getting to a business that generates passive recurring revenue.
  • Once your passive income exceeds your expenses and you’ve automated/delegated your way out of all activities besides cashing checks, then you are truly free and can allocate your energy however you like.
  • Find mentors who care about you and are unconditionally invested in your success. As you build your network make a mental bookmark when you meet someone who you think you could learn a lot from and have good rapport with. Then just ask them if you can buy them lunch and learn about their journey. Likely they had mentors themselves and get the concept of “pay it forward.” People who don’t get that concept are not good mentors so self-selection is working in your favor in this regard. Keep knocking on doors until you have a bullpen of good mentors.
  • For me my godfather was this role in caring inherently about my well-being and then over time I built a small bench of mentors who I periodically check-in with to get their perspective.
  • Masterminds are incredibly useful. These are small accountability groups of people roughly at the same phase sharing insights and getting/giving advice. Together with the mentor bullpen these two resources are invaluable in surfacing unknown unknowns. You can typically find a mastermind in your local area with some searching.
  • Personal development programs can eject you from a rut. I did Tony Robbins’ 30-day “Personal Power II” program on CD set and the day I finished it was the day I got my first real job. Robbins doesn’t resonate for everyone - he can be too “motivational speakery” for some. It’s less important which particular personal development program you use as much as it’s about forming habits and discipline of “sharpening the saw” as Steven Covey would call it.
  • Read this interview with Naval Ravinkant. He did a now-famous tweet thread on “How to get rich without getting lucky” and his advice is timeless and spot on. If that resonates read his Almanack. He has a pod too. Naval is a sage and a personal hero.
  • Derek Sivers is a legend. Just read or listen to whatever on his site resonates with you and you can’t go wrong with him. He has a short-form podcast too which is good.
  • Start playing with AI platforms like GPT yesterday. LLM’s are going to be as transformative as the advent of the internet was. People who are using them for writing emails and blog posts are just scratching the surface with the power of these things. Talk to them like a teammate or research assistant and don’t get paralyzed trying to find the optimal prompt- just start a conversation, give it objectives and zigzag your way to finding answers. LLMs are now powerful enough to perform both a tutor function as well as an implementor function. While AI will indeed wipe out some subset of jobs, it’s going to give superpowers to the people who are early with it and figure out how to most effectively leverage it. Nocode, automation, AI, outsourcing… these are all amplifiers that give you leverage and they compound when you stack them.
  • Start learning the basics of web3. AI and web3 are probably the two most important tectonic shifts that will reshape society in the coming years so why not seek to be ahead of the majority in understanding the mechanics of how they work? Massive entrenched industries like lending, insurance, credit bureaus will be disrupted and rendered obsolete within our lifetimes. If that’s not reason enough to explore web3, cracks are showing in the traditional financial system. Now is the time to gain some financial sovereignty, diversification and establish a basecamp in web3 world. Metamask Learn is a very good, free way to get up to speed on the basics and start getting your feet wet in this world. Worst case, you gain some basic familiarity with web3 concepts that will be valuable as web3 gains mainstream adoption. Best case you might decide it’s your jam and take a job in this space (there are many to be had). Bankless is a beacon in this realm and great at making these concepts accessible. Remember this: blockchain/web3 =! cryptocurrency. The money use case of web3 tech is actually one of the least-interesting applications of it and just a subset of the space. It’s what else can be built on top of a trustless, distributed database that is truly revolutionary.
  • Once you learn your ideal career then it’s a matter of finding or creating the job within it. If entrepreneurship is your path drop everything and take Steve Blank’s free Udacity Course. This is hands-down the best framework for doing a startup in a risk-reduced and time/capital-efficient manner. I wish I could have taken that course before we started JumpBox. It would have saved so much brain damage and indigestion.
  • If you’re not creating but rather seeking to get a job (Mark Suster’s essay " Is it time to earn or learn?" is worth a read) be clear about the parameters that you are optimizing for. Wellfound (formerly Angel List) is arguably the best platform (you can filter by “remote-friendly”). You can also leverage ChatGPT to get creative in finding job listings that match your params. RemoteOk is also a good search platform.
  • Start a blog/newsletter (Substack or better yet Ghost). Short-form social media robs us of our long-form writing mojo (myself included). But starting a blog helps you in so many ways:
    • It builds the writing communication persuasion muscle and is the offsetting antidote to ADHD social media that kills our attention span.
    • You can fake a resume but you can’t fake a blog. I would 1000x rather see someone’s blog than their resume when hiring. It shows how you think, what you care about, how you handle criticism and what you value. And it’s preserved by so verifiable unlike a resume.
    • It leads to serendipitous in-bound connections you would never get otherwise. People search for stuff and find you. It’s like inbound marketing but for you.
    • It keeps you accountable for your ideas and there is a virtuous circle of writing begets thinking begets more writing, etc.
  • Lastly, this post by Kathy Sierra (another one of my heroes) floored me back in the day. If all these ^^ inspiring positive reasons to start a side hustle aren’t a strong enough carrot, here is a menacing stick that may convince you: Under-stimulation gives us a form of brain damage which then makes it harder for us to actually perform (vicious cycle). I was stagnating in a corporate cube farm very much like the environment portrayed in the movie Office Space and this article tipped the decision to leave. It was slow-boil frog situation: I wasn’t happy and yet wasn’t uncomfortable enough to leave an easy corporate job that paid. This piece made me realize that the grey, under-stimulating cube farm was in all likelihood quietly stealing my future brain power. If it feels like a job is making you brain dead, it likely is. Think about that and the ramifications that has.

Summation of all this: the Problemattic Way is a guide I put together for team leaders at our events and has a ton more resources that I have compiled over the course of my own entrepreneurial journey. I also write about nocode, automation and mental models on Grid7 and interview some amazing people via the Problemattic Podcast if you need inspiration to make a move.

Lastly, remember this: while career decisions can seem like irreversible choices, unless it’s a transition to kamikaze pilot, they aren’t. They’re largely Type 2 decisions. I’ve changed careers now 5x over the course of my working life and had it not been for all the diverse roles I played previously, I would not have had the unique mix of technical, sales, automation, writing and direct response marketing that enabled me to excel in my Pagely role. What appeared from the outside to have been indecisive flip-flopping was actually the unique forging of an unlikely mix of weird disparate skills that allowed me to uniquely see and implement solutions for what Pagely needed. As Steve Jobs famously said,

You can’t connect the dots looking forward; you can only connect them looking backwards. So you have to trust that the dots will somehow connect in your future.

Every time we go through a switching cycle we pick up a useful new vantage point that helps us figure out the dimensions of our radar chart that matter most to us so we can dial it in better next time.

Anyways, now you now know everything I wish I could have told myself when navigating a period of professional change.

Good luck as you figure out the next chapter. Let me know if there’s anything I can do to help.


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Great read Sean! I am currently in a transition and I will definitely pick up some aspects. I find the most difficult thing to be the combination of doing something we like and living of it, especially in the early days of a side biz/startup.

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