I missed my daughter’s first steps because I was in meetings I don’t even remember.
It didn’t feel like a big deal at the time. But years later I still remember the moment Sheila texted to say it was happening… and not one thing about the meetings that day.
We knew it was going to happen soon. But it felt silly to work from home for the week just to try and be there for the moment. As a C-level exec in the company, I technically had the flexibility to do it. But it didn’t feel like a good enough reason to skip the company’s mandatory in-office policy at the time.
This was just one of hundreds of small sacrifices I made to put career in front of life and family.
This was also a key moment that shaped my Time Value of Life philosophy that I wrote about last time.
I sat through thousands of meetings during my 16 years in the corporate world. Most of them were about nothing in particular. Many were just minor variations on the same thing over and over. I could have missed hundreds of these and my life and career would have been no different.
But missing out on my daughter’s first steps was literally a once in a lifetime event.
A lot of people I talk to have similar experiences and feelings about their evolving relationship between career and family. They’re looking for a way to balance more evenly between earning and living.
They come to me because they feel trapped in their corporate careers. They want to take a different job they feel more passionate about or be able to spend more time with their families but are worried they can’t afford to take the pay cut.
They often have more financial flexibility than they realize.
Bridging an Income Gap Between Reality and a Dream Job
Here’s a simplified example of the kind of conversation I have with people in this situation.
- Jim and Sarah are both 38 and have two young kids. They’re like you and me. They live in the suburbs of a major city, shop weekly at Costco, hang out at the local brewery with their kids and friends on the weekend, etc.
- Their total yearly spend across their mortgage, preschool, and living expenses is $200k.
- Jim earns $80k a year after taxes at a small, independent marketing firm and loves his job.
- Sarah is at a big law firm and clears $300k a year after taxes and maxes her 401k each year. But she travels all the time and is burnt out. She wants to go in-house at a local company where she can feel more ownership over the impact she has each day and be home more with the family.
- Unfortunately, the company will only pay her $90k a year after taxes.
A quick mental calculation shows Sarah’s $90k + Jim’s $80k is less than their $200k in living expenses.

Sarah really wants to take the job but the $30k shortfall is far from a rounding error. She feels like she can’t take the job without majorly reducing the family’s quality of life. She’s also worried about risking their retirement because there’s no room in this budget for 401k contributions.
So we sit down together and look at the bigger picture.
Beyond their income, they have $750k in retirement accounts already and another $700k in their brokerage account, primarily invested in an S&P 500 index fund.
We identify three areas together that will help Sarah take her dream job and spend more time with her kids.
Costs: We map out all their costs and find there are $6k a year in convenience expenses that we could easily eliminate if Sarah is working more reasonable hours and traveling less for work. These convenience expenses are common in families with busy professionals and include frequent DoorDash orders, last minute childcare, etc.
Investment Income: Instead of keeping all $700k of their brokerage account invested in the S&P 500 index fund, we move part of the portfolio towards a diversified income strategy that aims to cover the $24k a year remaining expenses. We do this through a mix of dividend stocks, private real estate funds, and bonds.
Retirement: We model out how much their retirement accounts could be worth in the future if, in the worst case, they never contribute another dollar. $750k growing at 8% a year for 30 years = $7.5 million by the time Sarah and Jim expect to retire. We find this is more than enough to cover their expected living costs in retirement. This analysis helps Sarah realize putting more into retirement at this point is a nice to have, not a must have.

This is just one of many ways to create a bridge from a high-paying corporate job that no longer fits who you are with that dream second act. One of the reasons I got into financial advisory is because I enjoy talking about investments and the markets. But I’ve since found the most rewarding projects I take on are the ones where a few hours of financial engineering helps someone take that dream job or step back for awhile to spend more time with their kids while they’re young.
It’s a path I know well. I left my C-level corporate job for a second act that felt more meaningful professionally and more rewarding personally. Missing my daughter’s first steps was a valuable lesson. It’s one I only had to be taught once. I got to see my son take his.
Nathan
Founder & Lead Advisor
P.S. — If you’re stressing about a version of Sarah’s $30,000 gap and don’t know what to do, that’s exactly what my Financial Runway Tuneup is for. Two sessions with me. A customized financial strategy and playbook you can run with afterwards. It’s just $599, with no ongoing commitment after. Email me at [email protected] to get the conversation started and see if we’re a good fit for each other.
Kangpan & Co. is a fee-only, registered investment advisor specializing in helping mid-career professional navigate the work, life, and financial tradeoffs that define their 30s and 40s.
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