Planning for the Future

Planning for the hazy “someday” of the future is tough. It's like peering into the mists of a foggy morning. Shapes are indistinct and intimidating until you get close enough to recognize the giant shadow is an oak tree.

I'm peering into the foggy future, but I can't make out what those looming shapes are.

People keep asking me what my next few years are going to look like, and I honestly have no idea.

So many things could change. There are just too many variables to have a plan and actually stick with it. And it's not just one facet of my life….. it's every part of it possible.


As many of you know, I'm single. Now that I don't have a definite end date to this job, I'd like to find a partner. It gets pretty tricky, though. I'm living such a drastically different lifestyle from my male peers that finding a compatible partner is not going to be easy. Fortunately, I'm willing to wait for the right guy instead of settling for whoever shows interest first.

I met a guy through a networking event for young professionals. We hit it off and exchanged numbers. I thought I had hit the jackpot. He was attractive, had a great job, funny, owned his own house with a roommate to cut the costs, drove the same car as me until it died and was replaced with a newer hatchback, great cook with food from Aldi and more.

After getting some rather confusing and conflicting signals from him, we had a talk one night (at 1 am aided by a lot of alcohol). He said he liked me, got along well with me, and could see us working out.

BUT. (there's always a but).

He firmly believes I'm going to fail at this early retirement thing. I'll admit, it stung a little, but it's also something a lot of older and wiser people have told me. Because of that conviction (which he refused to get my input on at all), we were dead in the water.

The thing that bothered me the most was him judging my past and extrapolating it into the future. I do things differently as a single lady than I do as someone who's in a relationship. I sleep with my baby blanket and a big pillow when I'm single. Do I do that in a relationship? Nope. I'm making plans AS A SINGLE LADY to try my best to get an expat assignment for work. Would I still go after that with a partner's career to keep in mind? Probably not, unless said partner wants to go with me and can make it work with their career.

What this guy doesn't understand is that my plans now as a single 26 year old can and probably will change. The actions I'm taking now- maxing out my retirement accounts, buying rental properties- will give us flexibility in the future. Quit my job and try to make a living as an artist? Sure, we have savings. Have a kid and want me to stay home with them? Done, we're living off one income anyways.

I wish I could change my plans to accommodate possible future changes, but since I can't predict the future I'm sticking to the plans I'm making now. I'm working off the information I have available to me right now. For the next guy, I will have to emphasize my plans are my own and I'm open to ideas.


Another guy I went on a date with could not fathom me wanting to travel. He was more than happy with his house, patch of land, and his great career. I knew we weren't going to be compatible when I mentioned I went to Ecuador by myself and his face paled at the idea. We didn't talk much after that which didn't bother me nearly as much as the first guy. Sadly, around this area (and probably much of the US) his idea of normal is much more normalized than mine.

Speaking of normal……. it's normal for people to have careers, and to discuss with their manager where they want their career to go in the future.


The older I get the more relevant Dilbert is

Of course I can hardly do things the normal way. That's just not me!

Unlike about every other FIRE blogger I know, my immediate manager knows of my FI plans.

Now, I didn't just trumpet my plans to my manager the moment I started. Nope. My current manager started out as my friend and coworker. We're still friends (we do play on the same softball team, after all)- we just have the added complication that he got promoted to team lead…. after I told him about my plans.

While not necessarily the outcome I would've chosen originally, I think it will actually work out well.

It helps my manager is younger than many of the managers around here, and thus more open to the message I'm getting across. He told me he and his wife have tentative plans to retire in their 50's, but hearing my plan for 30's blew his mind!

I've made it very clear to him how much I enjoy this job, that I don't have any plans on leaving any time soon, and that he will know what my next move is before I make it. I'm actually not upset at all, as he's already been helpful brainstorming some ideas for the future with me.

That leads to the problem though…. what is my plan for the future?

In a typical one-on-one, I'd get help crafting my internal resume to look attractive to assist me getting my next position, or a job that will help boost me to the next level.

I have an idea what I want my next position to be, and where I want it to be. I could probably even make it happen seeing as I know the whole chain of command all the way up to the top.

Even better, they all know my name!

I really, really, really want an expat assignment. Somewhere like Thailand, Singapore, New Zealand or anywhere in Europe. One perk of working for a global organization.

However, expat assignments are hard to come by these days. They're incredibly expensive for the company, what with the level of paperwork that goes into it, the classes to get the employee prepped for their new home, and then the logistics of getting all their stuff over to the new place. As well as a few more I don't know.

But…. I still want to go. It'd be a great way to travel around a region from a home base without having to use up tons of vacation or suffer through 18 hour+ flights. IN ECONOMY. THE HORROR.

The beauty of being on this path to FI is I have options. I'm willing to use up every bit of social capital and power of FU money I have to make it happen. If I lost my position in the company because I pushed too hard, I'll land on my feet.

I'm just going to wait until that's possible!

Thanks for reading! How do you think I should broach my FIRE plans on dates?

Join my email list!

Subscribe and get access to some really cool stuff!

Powered by ConvertKit

35 thoughts on “Planning for the Future

  1. Hey Gwen! I am kind of in the same boat – as an independent person who has done a lot of traveling and hopes to do more, I wouldn’t be able to settle for someone not interested in leaving their own town. As far as goals, I think it’s important to talk about what goals you have and how you plan on growing as a person. It’s a huge red flag to me if people don’t have goals for themselves or think they won’t change over time. However, I think it naturally flows into a conversation about how I’ve worked towards goals and how some of them have worked out, some have changed, etc.

    I would never have planned to end up where I am today – N-E-V-E-R. I wouldn’t have been able to conceive of it. But I’m making the most of where I am and really enjoying the process. Because, after all, isn’t life about the journey, not the end goal?

    • Life has a funny way of working out like that, hey? I would’ve also been hard pressed to imagine a life like mine if you’d asked me in the past. I honestly can say I love it! Thanks for commenting!

  2. Aww, sorry about those guys. But hey, with dating you’re finding out what you do and don’t want in a partner, and that’s invaluable. 🙂 To be honest, Mr. Picky Pincher probably would have thought I was insane if I were on the path to FIRE and told him while we were dating. I don’t think it’s wrong for a potential BF to doubt how you’ll achieve FIRE–but it’s definitely wrong for the guy to be adamant, bull-headed, and hurtful about it. Consider that one a bullet dodged. 🙂
    Mrs. Picky Pincher recently posted…79 Ways To Have Fun For Nearly FreeMy Profile

    • More like a cannon ball. I also failed to mention his need for ADHD meds. It wouldn’t be a big deal by itself, but he also has a slight drinking and chew problem. GROSS.

  3. A person who makes up their mind based on little to know data and then stubbornly refuses to discuss the idea is hardly a catch. Good riddance. Here is my dating advice for you: focus less on actual financials and more on the persons dreams, aspirations and ability to think through the things in a way that is similar to you. If you find a person who is currently not financially savvy but has these properties you will be able to convince them to join you on the FIRE path. If on the other hand they have a 70% savings rate, but never want to travel that isn’t going to result in much happiness.

    I hope you land an expat gig. That will be super exciting, and depending on location, could be such a boost for FIRE.
    Mrs. BITA recently posted…Long Term Capital Gains, Roth Conversions and Harvesting GainsMy Profile

    • I take the overall financial picture into account, but I don’t pick and choose solely off that. I would feel like a gold digger if I did that! I’ve been working on meeting people doing things I like to do- working out at the bodyweight fitness site at the nearby park, during bike rides, at the local Makerspace, softball, and the area Real Estate Investing group. Thanks for the *good* words!

  4. “He firmly believes I’m going to fail at this early retirement thing”.

    Yeah, so eff that guy. Sounds pretty arrogant and judgmental to me. Not to mention that you are doing better than the vast majority of people your age in terms of FIRE. None of us are perfect but a potential partner should be encouraging and enthusiastic, accentuating the positive rather than focused on the negative. But hey, you can use his comments to fuel and motivate you to kick ass, so at least he was good for something!

    • Wow have you met him in real life? Nailed it. Proving people wrong is great fuel for my motivation! Thanks for commenting!

  5. Just be yourself. Be honest. I am not a big fan of “crafting” a certain perception or image or catering to an individual if it means you need to comprise being who you truly are. If they don’t like you for who you are, then they’re not the one! It’s actually very helpful to think this way, IMHO. And it’s a natural disqualification process =)

    • Trust me, I turn a lot of people off just by being myself. But I am definitely not willing to compromise who I am just for the sake of having a partner. I would be miserable!

    • Thanks, Taylor! Wouldn’t it though!? It’d be so much fun to get to explore and really figure out how another culture lives for a while.

  6. You do have some older readers, like me! And us old guys always want to give advice to you kids. We’ve got three kids, all millennials. My advice is stay picky about guys. You are an outstanding young woman with tech smarts and financial smarts and you have all the time in the world to find the right partner. We’ve been married 39 years and mostly we’ve succeeded because we agreed on money, our faith and have shared hobbies. Strangely the last one of those might be the most important. We endurance run, snow ski, fish, hike, bushwhack, travel and play competitive tennis together. I know those sound like active hobbies for 60 plus people but we are maybe a little more fit than most. Hold out for that guy that sees money the same way you do, has similar values and does things you like to do. And he will be one lucky guy!

    • I love getting advice, especially from those who have been there, done that, and gotten the T-Shirt! Since this is the one thing that will arguably have the most impact on the rest of my life, I’m not making any quick decisions! I’m going to take my time. Since I have a wide range of hobbies, it shouldn’t be difficult to find something in common! Thanks for the wonderful words of wisdom!

  7. Hey Gwen!

    Of all the qualities that get talked about when it comes to looking at a potential partner, open-mindedness tends to get the shaft in favour of some of the sexier qualities out there. And yet, this is probably one of the must-have qualities in your significant other when you’re coming from the FIRE background.

    Someone who is really open to learning and growing, and who enjoys being outside of their comfort zone (a great paradox!), is probably more likely to really buy-in to your life approach. While it definitely sounded like guy #2 didn’t fit this bill, from what I read, there was no evidence that guy #1 did either. Am I wrong?

    Over time, I’ve become more confident and effective at talking about FIRE as a concept to my friends, family and dates. We all know how attractive confidence is! I’m sure that through your own growing confidence, you will attract an amazing person into your life who will get on-board and grow with you on your journey.

    Happy hunting!


    • I LOVE this, Mike! You are absolutely right. He did not fit the bill, although he’s come closer than almost anyone I’ve met.

      Good luck to you, too!

  8. That’s too bad. To some people math is hard and they just end it at that (Safe withdrawal rates and the like)

    FIRE is a topic that most just can get their heads around. Maybe you will meet someone that is “normal” hears what you are trying to do and realize they are doing it all wrong and want to join you on the adventure!

    • Math is hard……. if we’re talking about stuff like calculus and differential equations. The concepts behind FIRE are simple, but complex to grasp since they go against the grain of pretty much everything society stands for. Thanks for the kind words!

  9. So you’re still single? Hi!

    You will not fail. Your current net worth and all of the blogs of people who have already done it prove that.

    • I mean, the math speaks for itself. I can’t do anything to make people listen to it, though 🙁

  10. I’m with the old dude, steveark. 😉

    Hang in there, girl. He’s out there somewhere. Whatever you do, don’t settle for less. It’s better to be the compete you right up front (which I know you are) and see if they can handle it then to try to fit into whatever cut out they think you (or any woman) should be. Us chicks are a rare bird to find. Naturally it’s going to take a while to find the right match. 🙂

    • I will not settle on something so important! You can take that to the bank! (preferably the same one where I hold all my fat stacks hah!)

  11. “The beauty of being on this path to FI is I have options.” This, to me, is the key to FI. It buys you flexibility and options. It is hard to plan the future. Even people that think they have their future perfectly planned are usually wrong. FI gives you the flexibility to make the best out of each situation you face and find the path that makes the most sense for you.
    Matt @ Optimize Your Life recently posted…On Quitting and Time ManagementMy Profile

    • I mean, I can make plans all I want. I hold zero expectations that they will work out, though. Good thing I have contingency plans for everything!

  12. Haha I can relate to finding Dilbert funnier the older I get. I think it’s cool that you’re open with the guys you date about your goals. Finances are a big deal in relationships. It makes sure your not wasting time with people you aren’t really compatible with. Good luck getting the expat assignment, I’m sure everything will work out for the best as long as you keep moving forward like you are.
    Matt Kuhn recently posted…5 Reasons Why Frugality May Be Holding You BackMy Profile

    • It’s a great test! Either they think it’s great, or they stare at me in befuddlement and we’re done. I like easy filters like that.

  13. It’s definitely very tough to find someone in the same financial situation and with the same mindset at our age, Gwen.

    I ended up going on a date with a girl the other week who had similar thoughts on early retirement. That being said, there was some thoughts I had were I didn’t entirely think she was being authentic. Just another one date and done I suppose.

    I’ve also definitely stopped dating a girl when I found out she had 50k+ in student debt as well… oops.

    Regarding career, there is definitely a fine line between telling your manager your plans and keeping them a secret – it’s equally as tough when you are super passionate about those plans. I told my manager about my business plans, and I can tell that he now is a little bit worried I may up and leave and for that reason, might not be willing to devote additional resources to me. Ugh.

    Thanks for sharing Gwen.
    Erik @ The Mastermind Within recently posted…25 Things for My 25th BirthdayMy Profile

    • I bet that girl had dolla signs all over her eyes after that date! It’s tough avoiding the gold diggers or being a suga momma. I think we in the FI world treat money so much more casually than everyone else. We talk about money all the time and it’s no big deal. Not so much to the rest of the world….

      As for the career thing, I honestly feel a bit bad that my experience is going so well and so many others have issues. Your manager’s response is much more typical than mine, sadly. Hang in there Erik!

  14. Hi Gwen! I just started reading your blog and I don’t know your full story, but you remind me of myself ten years ago. I heard your interview on the Mad FIentist and I am so happy to be following your journey.

    I’m 36 years old and I FIREd in July 2016 after 9 years in the tech space. I spent the last three years based in Singapore travelling and working all over Southeast Asia. I had a cushy job back in Scandinavia, with great pay, retirement pay, 6 weeks of vacation every year and working hours between 9-4 pm (I know!). However, I decided that adventure trumps money and I have never regretted going to Asia. A lot of the Early Retirement bloggers dream of travel, but in my experience, getting the opportunity to work with locals and travel on the company bill is pretty fab, too.

    Though I understand your frustration about useless dudes on dates, I wouldn’t stress it. You are young and as you say yourself, meeting someone now might cramp your style and limit your opportunities. I was fortunate enough to meet a guy who supports this idea I have most of the time, even though he isn’t ready himself and does relapse at times, asking me when I am going back to work. I just tell him to not worry about it. 😉

    Might I suggest going for a local contract in Singapore or Bangkok? If you think an expat contract could be difficult to get, they are always looking for skilled tech people in Asia. Oh, and those prep courses and sending your stuff overseas? I sold everything I owned and just moved with two suitcases and figured the rest out. As will you!

    • Hi Anna! Thanks for commenting! Everything you said sounds exactly what I want to do in life! 3 years based in Singapore! Wow. Amazing.

      With regards to the prep courses and sending the stuff, I was referring more to my company’s policies for expats, not necessarily what I would do if moving over there. My individual plans would look way different if I went overseas on my own!

  15. No one said the journey to FIRE was glamorous. There are other obstacles besides just living frugally. Obviously dating is a big one. First off it is hard to find and meet people as you get older, especially people that share the FIRE interest and lifestyle.

    I did laugh when you mentioned people being “older and wiser.” My uncle gives me crap for my views all the time. In society he would be considered older and wiser. Nice house, multiple kids, making probably 100k working for a big reputable company. But when it comes to net worth or even having extra spending money, they struggle. Probably will have to work till retirement age. So are they really wiser? Especially when you are flourishing and setting yourself up better for the future.

    I wouldn’t worry too much about it. There are tons of people out there, I know the struggle all too well. Just keep striving for your goals and the rest will fall into place.
    Dividend Daze recently posted…Small Savings, Big ImpactMy Profile

    • Seems glamorous from the outside! However we wouldn’t be doing anyone any favors if we glossed over dating issues, career problems, or the struggles of starting out in real estate. When older people laugh at me or patronize me for my plans, I just use that as fuel for my FIRE plans. Nothing motivates me more than people saying I can’t do something! (Except maybe food. I am highly motivated by food.)

  16. Hey, Gwen. Sorry to hear you hit a rough patch on the relationship front. Guys, especially young guys, are very strange beasts. And I don’t think our culture is helping matters. We seem to be producing an awful lot of mama-boys. Where are the men? Where are the adventure seekers? Where are the men who aren’t satisfied with normal, who want to do more with their lives than excel at video games? I wish I had some wisdom to impart on this matter, but I don’t. Sigh.

    • Funnily enough, I know they’re out there. I see them in the news all the time. Problem is, either they’re already taken, too busy for a solid relationship, or live someplace cool and exciting. Aka basically as far away from me as possible. My town is full of traditional ideals- get a good factory job, settle down with a nice partner, buy a house, and raise kids in a house surrounded by a white picket fence. I suspect I’ll have to move to find someone more compatible with my mindset.

  17. Hmmmm, tough one, my wife and I weren’t into FIRE when we were dating so I cant comment on that specifically but I can comment on how we discussed our finances. Basically we didn’t. At least not directly. We alluded to our financial situation by talking about how we viewed money/finances.

    We never talked about our finances directly. I never asked her how much debt she had. We didn’t review our budgets together. But we knew that we were on the same page when it came to our finances based on all those other conversations.

    Personally, I wouldn’t discuss my FIRE plans while dating unless its getting serious. It’s not something they need to know right away. FIRE is an outcome. FIRE is the result of how you approach/use money. Talk about your views on money/finances and see if they feel the same way.

    Take this with a gain of salt of course. My wife and I started dating almost 15 years ago. So its been a while 😉
    Owen @ PlanEasy recently posted…The Simple Retirement PlanMy Profile

Leave a Comment

CommentLuv badge