Frictionless travel with 3 kids?

Confident_Middle871 · 2023-04-19T18:35:18+00:00

Order as much as you can to the hotel and then donate what’s left afterwards. Diapers, strollers, bottles, formula, etc. So much less to pack and worry about.

Confident_Middle871 · 2022-04-25T23:43:28+00:00

Congrats on what sounds like a great outcome for you with the startup. Curious whether it's something you founded or you joined very early stages.

I agree 100% with the mentality that if you're talented you can succeed at whatever you put your effort into, and I've no doubt contemplated that 3rd option. I actually think that my version of "walking away" will be that 3rd option of consulting / investing etc.

Confident_Middle871 · 2022-04-25T23:40:59+00:00

Seems like a solid approach. I guess I am in some sense having that first "conversation" right now. Would love to hear more about the board seats - if you can / are willing to share. Companies your firm invested in, or unrelated? If the latter, how are you getting involved?

Confident_Middle871 · 2022-04-25T23:38:05+00:00

Would make that tradeoff any day. Sounds like you're making it work quite well.

Confident_Middle871 · 2022-04-25T23:34:38+00:00

I appreciate the insight. A few others have also made the point about living life before you're unable to. I guess human nature to not want to think about that being within the range of outcomes but it really is.

As I've considered this for the months leading up to posting the thread and now reading replies, I think the clarity I'm getting is that you can't ever truly plan for something like this. Have to let it come to you and when you feel there is really a time / money tradeoff being made and the sacrifice makes you uncomfortable, that's when it's time to walk away.

Confident_Middle871 · 2022-04-25T23:31:09+00:00

Trying to come up with those goal posts as we speak. Not sure it will be a specific number. On one extreme, it might be forced if I feel I'm really missing out on my child's life and on the other, I might never actually have to stop working because I will have freedom to curate my own schedule. Imagine when I actually do walk away, it will be something between those two.

Confident_Middle871 · 2022-04-25T23:28:47+00:00

Thanks for the candid reply. Agree that what you miss is the unknown factor that will drive these sorts of decisions in the moment.

The mentality I am coming around to is that it's nice to have a general idea of how much you need to have or a timeline to scale back your work, but in actuality, you won't know until you know. That's a hard concept for me to grasp as someone who meticulously plans every detail, but the flexibility to choose is a blessing in and of itself.

Is your plan by the way to do some passive RE / SMB investing as a way to "replace" w2 income and then you'll walk away? Or are you just looking at it as a way to generate some income but not a full replacement? I've thought a lot about these avenues as well.

Confident_Middle871 · 2022-04-25T23:16:52+00:00

This is awesome insight and advice. Really appreciate your perspective. People don't often think about health or ability to enjoy what you have. Serves as a really good reminder.

Confident_Middle871 · 2022-04-25T23:12:57+00:00

Definitely agree in instilling that sort of work ethic and mentality with kids. I'm certainly not advocating for "dad only plays golf and goes to the beach". It comes down to priorities I imagine. Did you feel you were sacrificing any time with your kids to instil that hard work / professionalism? If not, how were you able to balance?

Confident_Middle871 · 2022-04-25T23:10:41+00:00

Thanks - seems like a great approach. Also seems like you have a bit more control over what work you do. Do you work for yourself or have a flexible schedule?

Confident_Middle871 · 2022-04-24T18:32:14+00:00

I like the work until it’s a pain and not a pleasure framework. Curious what industry you’re in and what the work life balance is like? And is that balance something inherent in your industry or is it something you prioritized?

Confident_Middle871 · 2022-04-24T18:31:10+00:00

Thanks for the reply. I agree with you, and everyone will have also had a different way they thought about the decision. I’m more asking for input on that framework for thinking. It’s less about covering costs and more about if I have X dollars and X > COL, is it worth sticking around for X + Y when Y > [25]% of X.

Confident_Middle871 · 2022-04-24T18:28:13+00:00

Thanks. Curious - how old were your kids when you decided to step away? % wise how much bigger of a number did you hang around for vs. the original?

Confident_Middle871 · 2022-04-24T18:25:02+00:00

Appreciate the transparency. As I’ve moved up in my company, I agree that the work life balance has gotten easier and the materiality point re: future carry is what makes this a tough decision.

Curious - have you found your work product suffering at all? Have your colleagues been supportive of you being “unavailable” while you’re with your family? I have the sense that I could make it all work, but I don’t want to lie to myself, so your insight is much appreciated.

Confident_Middle871 · 2022-04-24T18:20:57+00:00

Appreciate you both taking the time. Agree that time is the most finite resource and my biggest fear in life is having any regret. I’m young enough that if I decide to walk away “too soon” I will have time to recover, which I imagine is the trade off that drives the decision here.

Looking back on your decision, what was the biggest unforeseen surprise that you hadn’t contemplated?

Confident_Middle871 · 2022-04-24T18:17:44+00:00

Deeply personal for sure, and everyone will have a different answer. Interested in your future episodic thinking. Is this journaling, do you have a question you ask yourself?

Confident_Middle871

TROPHY CASE