I left a “dream job” last year after 20 years in high tech marketing, at the age of 42. I didn’t received a dot.com pay out, nor was I an early employee at Google or Facebook. I started my career at the bottom, making $21,000 a year. For the last ten years I worked at a non-profit that paid well and had outstanding benefits. The job afforded me travel, lots of Starwood Points and supreme flexibility. It also afforded me status, especially among those who revere the open source technology that touches our lives everyday. Even though FIRE (financial independence/early retirement) was my goal, leaving this job was incredibly challenging.

I’d been preparing for financial independence/early retirement since my mid-twenties. I got out of grad school and realized that working a corporate job was not very compatible with writing fiction (or being happy, at least for me). I saved and invested steadily, and never planned on working so hard for so long through my thirties and early forties. While my job was incredibly flexible, it was also incredibly demanding: growing from a tiny non-profit to a company generating over $50m a year in revenue when I left. I made a great salary, which made FI easier. But the status and “instant identity” from my job made it much harder to leave than I ever imagined.

Boo hoo, you say. You had to quit a dream job because you had money saved? Remind me never to feel sorry for you, you complaining jerk! I admit it — it does sound ridiculous. My grandmother raised 13 children on mostly one income, as a short-order cook in restaurants during the night shift. Can you imagine her massive eye-rolls at this discussion? (Actually I’m not sure she ever rolled her eyes. Didn’t have time for that.)

I have tremendous gratitude for these choices. I have tremendous gratitude for the privilege I’ve enjoyed being born in California and profiting from an amazing public education. I never expected to make as much as I did at the end, and so when I did, I saved it. I didn’t think my identity sprung from my possessions or my career, so I could walk away. But at least for me, the identity and sense of meaning attached to my career proved to be a complicated puzzle. Who would I be without my C-level job? Who would I be without all the busy-ness of travel, events and board meetings? How would my children see me? What would I say when people ask the inevitable, “What do you do?”

Geography also complicates it. I currently live in the San Francisco Bay Area where it seems almost everyone is involved in technology or fast-paced careers striving for a big payday. It’s gotten so expensive here that it’s a struggle that drives this endless striving. Everything is expensive.

Most early retirements resources are focused on the how. How to invest in index funds. How to improve gas mileage or not drive at all. How to use geographic arbitrage to retire earlier. How to optimize taxes. All of that is crucial and wonderful, but if you don’t have a why for early retirement,you may end up facing a chasm of uncertainty once you attain it. Not only is the motivation critical— I don’t believe most people will delay gratification without a pay-off in the end— but to some people FIRE can become just a game. Something they want to “solve.” And they put little energy into figuring out what they will solve once their all consuming puzzle is solved.

For me, I used my drive for creative writing as one motivator. I used my children as another. When you live in the Bay Area and both parents are working, it’s hard to be a great parent, at least for me. All that rushing and talking and traffic, got in the way of how I wanted to parent. My partner feels the same so we are moving forward with our plan to be fully financially independent as a family in five years. Another motivator was the fear that in the ageist world of technology, I didn’t want our family dependent on two incomes as we eventually entered our fifties.

These are great whys, but it still doesn’t solve all of the identity issues, especially in the US culture that puts so much focus on career. I’ve compromised by still doing some freelance work and some advising, even though it too takes from my creative and parenting pursuits. Is it the right answer? Or a cop-out? I’m incredibly grateful I get to wrestle with these questions, and that so many would love to have this “dilemma.” But for those of us seeking freedom through financial independence, the why is even more important than the how we get there. What’s your why of early retirement?