Redefining Retirement Planning Using AI And Ikigai

How to revolutionize your retirement: From 401K to personal investment

When it comes to retirement planning, everyone talks about investing in your 401K, but nobody talks about investing in yourself.

So today, I'll be sharing how to pivot towards investing in yourself by launching a small business that provides a steady income stream.

We're going to uncover the perfect business for you by merging a time-honored methodology (Ikigai) with a pioneering technology (AI).

But first, let’s talk about why you should care.

Why This Is Important

We are going to live longer, and we are going to be more productive past the age of 65.

We’re seeing it already. You probably know half a dozen friends and family members that are still living and being productive well into their late 70s.

Assuming you want to do what you're doing for another 20-30 years, do you want to be dependent on your current employer to keep you around?

And do you really want to be dependent on a 401k that may or may not be enough to sustain you that long?

I didn’t.

Back in 2007, I had a couple of coworkers who had to nix their retirement plans because their 401k’s were cut in half during the recession. And its been worse for some the past few years since the pandemic.

For my money, the best investment is in yourself.

So if you want to set yourself up long-term, start a business that prioritizes fulfillment and being the best YOU you can be. It gives you the most control over the money coming in and how much.

And money and security aside, this is a huge chance for you to start over and do something you always wanted but thought you had to wait until retirement.


Before you invest in a 401k or an IRA, you need to do some homework to make sure the companies you are investing in give your money the best chance to grow long-term.

The same applies to investing in yourself.

You need to know which skills, interests, and experiences of yours are the best to invest in for the long haul.

“The key to attaining fulfillment and excellence is a mindset that empowers you to fit your circumstances to your unique interests and abilities. This mindset can be rendered in plain English: Harness your individuality in the pursuit of fulfillment to achieve excellence.”

Dark Horse: Achieving Success Through the Pursuit of Fulfillment by Todd Rose, Ogi Ogas

To do that, you can use a tool that helps you find your ikigai.

Here’s what that is.

“Ikigai is a Japanese concept that means your ‘reason for being.’ ‘Iki’ in Japanese means ‘life,’ and ‘gai’ describes value or worth. Your ikigai is your life purpose or your bliss. It’s what brings you joy and inspires you to get out of bed every day.”

This image really drives the concept home.

Using myself as an example, here are the four questions you need to ask yourself to find your ikigai.

1. What gets me excited? (Passion)

  • Music

  • Success stories

  • Learning new things

  • Working with creators/entrepreneurs

  • Identifying and sharing opportunities

  • Marketing tools (geeky, I know)

  • Future of work

  • Podcasting

2. What I'm good at? (Proficiencies)

  • Evangelizing

  • Encouraging

  • Entertaining

  • Speaking

  • Teaching

  • Inspiring

  • Solving

3. What does the world need? (Mission)

  • More success stories.

  • More independent thinkers.

  • More people help people by doing more work that needs to be done, enjoying it, and gaining purpose from it.

4. What can I get paid for (Vocation)

  • Music

  • Teaching

  • Coaching

  • Marketing

  • Google Ads

  • Creating courses

  • Computer Aided Drafting (CAD)

This exercise was a huge eye-opener for me. I wished I had learned about it a lot sooner.

It would’ve saved me from wasting years of my life working in jobs and businesses that weren’t aligned with my ikigai.

But enough about me…

Let’s Find Your ikigai

You can do this on your own with a pen and paper. But you can save a bunch of time, learn a new skill and have more fun by using Artificial Intelligence (AI) as your personal ikigai coach.

Here’s how.

Go to ChatGPT and sign up if you haven’t already (you can use Google Bard too).

Then copy and paste this prompt into the chat box:

“Act as an Ikigai coach by asking me detailed questions about my life. Continue asking questions until you have a complete understanding of where my passions, proficiencies, purpose, intersect in a profitable way. Your goal is to develop a deep understanding of what I love to do and how I can make money at it. Once you are extremely confident that you understand my situation well, give me advice on what business I should start while being employed full time, with a goal of eventually transitioning from my full-time employment to my business.”

The AI will start asking you questions. All you have to do is answer them.

When you reach the end, AI will give you a few business ideas.

Cool huh?

Here are some of the business ideas the AI gave me:

  • Online Marketing Coaching Business

  • Content Creator Support Platform

  • Affiliate Marketing Expansion

  • CAD Consulting or Training

  • Music Marketing Consultancy

And for because I wanted a few ideas, I asked the AI to “list 5 more,” and it spit out the following:

  • Podcast Production Services

  • Speaking Engagements

  • Freelance Writer for the Music Industry

  • Google Ads Consultant

  • Online Community for Creators/Entrepreneurs

Interestingly, over the past decade, I've managed to generate revenue from several of these recommendations. Considering the AI doesn’t know a thing about me other than what I entered, I'd say this exercise is pretty accurate.

BONUS: Congratulations! If you went through and did this exercise, you just invested in yourself by learning a new skill. AI is going to be everywhere, so understanding how to use AI and pairing it with your current experience and skillset helps you stay relevant and gives you a huge leg up in whatever you pursue.


So there you have it. Don’t just rely on your 401k for your retirement, start investing in yourself.

Take the time to do this exercise and find your Ikigai.

And who knows, if you find and start a business you love, you just might be able to retire early doing work you actually love doing.

The Futures So Bright

Remember this one?

While I was writing this, an old ‘80s tune by the band Timbuk 3 popped into my head, “The Future So Bright (I Gotta Wear Shades).”

While looking up the song, I learn a few cool little facts about Timbuk 3:

  • They are husband and wife group

  • They are from Madison, Wisconsin (right down the road from me)

Check it out…

Once you finish your Ikigai exercise and have had your dose of music motivation, grab your shades and head over to the post on uncovering your unique capabilities.

I’ll show you how to discover that spark that will help keep you in control of your retirement plans.

See you over there,


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