30 Career Next Steps Questions

Random Observation/Comment #775: It’s okay to feel stuck. Reflect on what’s most important to you and try to move forward with baby steps. (Now I’m thinking about “What About Bob”)

Why this List?

Feeling unchallenged and bored at your current position, but the money is good? Looking for a new opportunity that’s different from the pigeon hole expertise you’ve built in the past 10+ years? It’s always a good idea to review your own skillsets and aim for positions with companies that can offer you different opportunities or better narratives that fit the things you care about. As long as you keep an open mind, you can apply yourself to any industry and find an overlap with your passions.

From a much earlier post, I have listed all of the standard career drivers and interests. From a more recent post, consider which 30 tech and industry trends might be interesting.

Here are some of the questions and my personal answers. I’m not writing this because I want to leave my current job (so stop constantly soliciting me, recruiters).

Take Note of your Current Career Trajectory

  1. Update your LinkedIn. What areas have you worked in? – Started in AI/robotics research –> Finance building eTrading apps –> executing projects for a consortium of financial institutions looking at the impact of enterprise blockchains –> Ethereum enterprise solution designs and DeFi protocols token/DAO launches + advisory/investments (on the side)
  2. How would you summarize your offering for a recruiter? – Technical solution architect with 8+ years of experience in blockchain dev and expertise in designing and delivering blockchain projects. Background in Finance (trading and IT applications), Crypto (market insights and token design), and Engineering.
  3. Out of all the positions you’ve worked, what felt the most rewarding? (This could be based on the narrative in work, type of work, difficulty/challenging, team-based activities, travel, etc) – From Dev to Business Analysis to Tech Lead to Sales Engineering to Solution Architecture to Sales Enablement to Product Marketing, it’s hard to say which one was the best. I liked the thrill of closing deals and client-facing plus travel time from the sales side. I also liked presenting workshops and designing solutions from the solution architecture side. Marketing is also pretty fascinating with how the products themselves get branded by your competitors.
  4. What are the amazing things about your current position? Is it just that the pay is good and you’ve created a great reputation and network? – Incredible people and challenging projects in a growing industry with a top tier/brand company. Day-to-day is never the same and remote flexibility to build at my own pace.
  5. What are the crappy things that you wish you didn’t have to deal with in the current position? Are you just bored? – Nothing that crappy. I was hired with a high salary from a competitor so while I do feel like I add tremendous value, departments don’t want to take on my headcount. With that being said, I also do work with a startup mentality where every problem is an opportunity to help (even if it is outside of official role).
  6. What would be the “typical” next step for a person with your skills? – A fairly boring next step would be to go work in some enterprise blockchain group at a bank, consulting company, fund, accelerator, or new startup. I don’t think I can go back to “enterprise”, but it would be very lucrative. Working at a fund or accelerator could be fun.
  7. What would be the “radical” next step for a person with your skills? – I could be a DAO freelancer consultant and break into a new niche. I would love to get into more advisory and board positions. I would also love to work at a foundation for a Layer 2 network or somehow move into non-profit areas.
  8. Realistically, what level are you looking for in the next phase? Level 7 managing a portfolio of $100M+? Director? CSuite? – My last official title was a Director. Since I work in a weird space, my next level role would probably have a fun title name, but likely sit 2 levels under c-suite. I only say this because I am a principal individual contributor at heart and don’t want to manage people in this stage of my life.

Lifetime of Learning

  1. What are your current skills that might be most transferable to other positions? Technical experience? Delivery experience? Client-facing? Presentations in a niche area? – Presenting workshops on complex topics at conferences or to customers in a consultancy level. Problem solving with deep knowledge in niche protocols, tech frameworks and dev languages.
  2. What resources do you have that might be a clear advantage? Years of experience in a niche field? Network Connections to companies? Financial security? Extra investment money? Runway for starting a company? – Definitely niche field experience and lots of connections with people always hiring from attending a lot of blockchain/finance conferences.
  3. What are your career path’s option expiration dates? Are there exams or major titles you must reach before getting to a higher position? – I don’t think I need to get an MBA or additional credentials to move to the next level. It would be nice to get on a board somewhere, but that usually requires significant investment and c-suite level expertise in order to elevate the company (or you’re just a board of a startup that doesn’t pay you).
  4. List the areas that you’ve grown in mastery. What can you talk about at a party endlessly? What is your passion subject or area of greatest contribution? Subreddit posts? Active volunteering? – Crypto history, architecture and current insights, Designing web apps and web3 dapps, Writing lists of 30
  5. How do you challenge yourself outside of work? – Building side projects, writing lists of 30, analyzing markets and macro economics
  6. What are your hobbies and would any of them be interesting as a full time position? – Writing, Table tennis, Photography, Cooking, and Traveling (as a hobby). I’ve tried doing all of these for pay, but never liked overlapping a passion for a job.

Personal Preferences and Perks

  1. Would you like to be an individual contributor (more discrete deliverables specific to the industry) or a team manager (building up the team and defending/representing their progress)? – Definitely individual contributor. This doesn’t mean I’m not a leader, but I tend to lead from bottom up through delivery or within a project. I just don’t like running big company-wide meetings.
  2. What are your base set of requirements for your desired role? Remote first? Minimum base salary? Seniority? Minimal travel? Number of employees? Funding of department or company? Short notice PTO for child care? – Remote first in a well-funded department for a company from 50-500 people would be ideal. Salary is flexible, but knowing my experience and niche, the average is $350k to $500k total package compensation.
  3. What would make you move to a new position? Double pay? Stock options? More responsibility? More senior title? More autonomy? Better reputation of company? Opportunity to make a bigger impact? – Honestly, it would have to be the opportunity to make a bigger impact to the ecosystem. This could be helping run a foundation or building out partnerships in a new layer 2.
  4. Ideally, what would you like to do day-to-day? (e.g. % allocations to coding vs helping vs managing vs communicating vs presenting, etc) – All my meetings would be done by 12pm and I get to do deep work from 1-4pm. I’d have a percentage dedicated to onboarding and mentoring new joiners. I’d definitely want to keep presenting workshops to some capacity. I actually like client calls, but I don’t want to do more than 3 a day. Minimal amount of overhead in bi-weekly or status updates. An hour or so a day on keeping updated with news inside the company through slack – I over communicate internally.

Hard Passes

  1. Are there particular companies you wouldn’t want to work for? Meta because how it spreads misinformation? Consulting companies because the hours are too long? – I think I’m done with working for banks. Consulting in the short term does have too much travel. I’m still open to funds and accelerators because of the deep research and mentoring.
  2. Are there activities that you don’t want to do in your day-to-day? Driving? Commuting to the office? Traveling? – Commuting is definitely not okay anymore. My travel has been once every 2 months, which I think is manageable. I don’t mind meeting up weekly with local coworkers for coffee or a whiteboarding session.

Reaching Out

  1. Which people from your career do you consider to be mentors? Are you still in touch? – I love my mentors. They’re either old bosses or colleagues that have been positive influences in my life. This does remind me to reach out to them.
  2. Who in your network might be able to give you advice about their position (These don’t need to be mentors, but could also have been peers or cold messages on LinkedIn)? – Within a few telegram group chats and whatsapp groups, I think I know a few people that could provide insight on running new networks or building companies.
  3. Talk to your peers in your current company. What do they see as a next step in their career path? – I love the friendlies. Even those who have left the company are great contacts for peers.
  4. Talk to friends and older neighbors. What career path did they follow and do you want to lead towards that path? – Northend beefcakes! We talk more about beer and parenting, but I’m totally down to talk next steps at the next beer/whisky outing or poker/mahjong night.

Learn the Playing Field

  1. Make a short list of companies you’d like to work for. What’s the dream company + position and why? What are the similarities from this list? – The similarities from my list are all around protocol-level foundation work in the crypto space. It also includes public companies that may start a blockchain group.
  2. Consider the position’s responsibilities. Are there stepping stones you need for being able to deliver on these responsibilities? – Most positions do require more management or process of rebuilding a reputation in a new company. It’s a hard skill to quantify, but definitely a muscle I need to exercise.
  3. What are you actively working on improving that helps you get to your dream position? – I’m mostly just making connections and investments in the right areas. I think my exploration of technical skills in token design and protocol enablement are still helpful. I still read tons of papers and try to run end-to-end products.
  4. Do you want to explore new industries and have the same position? (e.g. Pivot to a new technology, but stay a product manager) – I’m pretty happy with my current industry, but I did think about 30 Tech and Industry Trends. I don’t know enough about the latest OpenAI software to apply it for a smaller company, but I definitely want to test it and apply it to different areas.
  5. What’s the market doing right now for your industry? Hiring freeze from scare of recession or reduced valuation? Hiring boom because they’re building a new team to explore a niche industry? – I suspect most companies will cut 20% during an upcoming recession.

~See Lemons Evolve in a Career