The Challenge of Planning the Transition to FI

I’ve often written about how I try to make the best of the journey to financial independence by integrating my core values and related activities in my present. While all of this sounds lovely and wise, in practice it can get really challenging and even more so when it comes to planning the transition to FI.  

Recipe for a desire to reach FI

The desire to reach FI often combines the following ingredients:

  • A deep desire for a sense of freedom.
  • An understanding of the importance of financial security combined with a desire to minimize financial risks.
  • Flavored with some discipline and various examples of people that have taken this path to look up to.

Now looking at that recipe, the 2 main ingredients definitely have some potential for conflicting priorities. Planning your transition to FI is very challenging, especially if the FI life you’ve envisioned requires you to leave a secure job. The challenge becomes apparent when your desire for freedom collides with your desire for financial security.  

At which point does having some financial security contribute to that sense of freedom? Does it happen in one single day when you hit a particular number in your investments and a switch goes off making you feel the sense of freedom? Is it gradual or does it happen when you hand in your resignation or the day you stop working?

Furthermore, the final ingredients that add flavor to the desire to reach FI, which are discipline and examples of people having taken this path to look up to, can contribute even more complexity to this puzzle. 

The courage to take advantage of your options

A recent episode of Jillian Johnsrud’s Everyday Courage podcast explored how Kiersten from Rich & Regular worked through her own challenges of planning her transition into entrepreneurship after being on the path to FI. 

In one of her questions, Jillian says:

“Sometimes, I feel like what took us from A to B all of sudden that exact same thing makes it hard for us to transition and take us to the next place we need to go.”

In line with this observation, over the course of the interview, Kiersten explains how, although equipped with the math that showed her plan had high chances of success, taking advantage of the option to leave her work to pursue entrepreneurship was a true challenge. Despite having experimented with longer and longer breaks from work, she had to work through her fears of quitting her job. A lot of mental work went into reflecting on what was holding her back and what was truly at risk.

In her post on this subject, Kiersten wrote:

Over time, we’ve become better architects of our own lives but, the thing is, you can know something is intellectually true enough to create a blueprint and still not believe it enough to take action and start building

As Jillian put it in the podcast episode:

Money does give you options, which is separate from being willing to take those options.” 

When your assets hold you back

I’ve since been reflecting on how that desire for financial security and the necessary discipline to reach FI might become obstacles that contribute to making the transition to using some of your accumulated freedom more difficult. 

Working less and slowing down the speed at which you were accumulating funds may result in uncertainty or hesitation in deciding which step to take next. Starting to withdraw the interest generated by your investments may cause you to feel some insecurity.

Even those examples of people you look up to, which can help propel you towards FI, can become less relevant as you get into your transition or as your life changes. Perhaps their own story of leaving work just feels very different from your own needs and where you’re at. 

It’s also why I strongly encourage anyone to read the Slow FI series to see many examples of people using their accumulated freedom in different ways. There really is such a variety of ways to approach this, and that just might be what makes it such a challenging process which often influences people to hold back from taking any action.

Finding a balance

The conversation between Jillian and Kiersten deeply resonated with me as I work on planning my own transition. Although our initial plan was to take parts of summers off from 2021 to 2025, these particularly challenging times have me thinking about making shifts as work has become a little much with all that is going on. 

After finding myself more obsessed with the desire for freedom and feeling signs of burning out, I decided to take some steps to add a bit more recovery into my schedule and discuss my options with my employer.

I’m lucky to have options available to me and a very understanding employer that is open to allowing me flexibility through these challenging times. The pursuit of financial independence also opens the door for me to options where my salary may be reduced since I know our needs will be met regardless. In the next few months I’ll dig deeper in reflections about what my transition may look like but I’m becoming increasingly interested in the option of Coast FI

If, like me, you start finding yourself getting more obsessed either with the desire for freedom or the focus on financial security, it might be a good time to take a step back to reflect on if something feels truly off balance. A change of plan might be in order to make sure you are staying true to your values and making the best of the journey while pursuing financial independence. 


Finally, wherever you are on your path towards financial independence, I believe it’s important to allocate time to do the mental work of reflecting on planning out your transition. 

Kiersten talks about how her own preparation to make the final move basically felt like a dress rehearsal where she would practice being FI by taking days and periods off from work. 

It makes sense to me that you would need to try on that freedom through actions in order to start truly believing & feeling it while adjusting the use of it as per your needs and values. In that sense, I’m focusing on various shifts that can help me experiment with that freedom throughout my transition. 

Every action you take is a vote for the type of person you wish to become. No single instance will transform your beliefs, but as the votes build up, so does the evidence of your new identity. This is one reason why meaningful change does not require radical change.” James Clear, Atomic Habits

Have you reflected on planning your transition for when you reach FI? If you’ve already made the big transition into a work optional life, any tips for the ones who are still on the path to reaching this goal?

2 thoughts on “The Challenge of Planning the Transition to FI

  1. There was no transition for me. I loved my job so I had much more than I needed when I did finally retire slightly early. I never even thought about the fact I was financially independent, never noticed when I reached the first million dollar net worth. I was having too much fun living life, raising kids and staying married.

  2. “staying true to your values and making the best of the journey while pursuing financial independence.” fantastic reflection. Isn’t that what truly matters?
    Left full time teaching at 56 from a job I enjoyed that had security. It wasn’t easy until I realized it is the risks that we don’t take that we come to regret. All the best on your journey.

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