Going Out on Top // Retiring at the Peak

if you watched yesterday’s super bowl, you couldn’t miss all the speculation that peyton manning is going to retire after this season, after clinching the most wins of any quarterback, and being the first qb to win the super bowl with two different teams. (for non-u.s. readers, or non-football fans, don’t worry. the football part of this post ends in approximately two sentences.) nevermind that peyton is 39 — the same age as mr. onl — and plays a sport in which that’s a perfectly acceptable age, if not a little old actually, to retire. what’s incredible is that peyton has the rare privilege of choosing to go out on top, on his own terms.

not many people, in sports and in regular working life, get that choice. many people who plan to work to 65 or beyond are forced to retire earlier by failing health or — worse — they die while still working. maybe they get laid off or fall victim to ageism, can’t find another job, and end up retired by default. even in sports, few athletes get to choose when they’re done. most often that choice is made for them by injury or declining performance, and they may just fade away while hoping a new team will give them another chance, or get cut unceremoniously by a team they’ve given their blood, sweat and tears to.

we talked about this a lot during yesterday’s game, how our situation is this very tiny bit like peyton manning’s (and unlike his situation in every other possible way). we’ve worked at our careers long enough to feel like we’ve had real careers, not just a stint doing this or that. we’ve climbed the ladder, and have seen the view from every level. we’ve earned the level of autonomy and responsibility that our younger selves dreamed of having one day. assuming no major tragedies befall us in the next ~ two years, it will be our choice of when we leave the game, and we feel pretty fantastic in knowing that we’ll be going out on top.

but going out on top is only possible because we’ve actually earned our way to the peak. we didn’t retire early when we’d only just begun to climb. while we may lament that we could’ve retired earlier if we’d figured all of this out sooner, the trade-off would be losing this feeling of a culmination. and we’re starting to think that maybe it’s worth it to be working a little longer in exchange for that feeling.

related: why we’re not going to complain about work anymore

enjoying the career arc

here in fire blogland, we all tend to talk — understandably — about our collective desire to exit our careers as fast as we possibly can. we have all these things we want to do, after all! artistic pursuits, athletic pursuits, travels and adventures, feats of self-sufficiency. it’s awesome stuff that gets us all excited, and we’re right to share that excitement with one another. but we got to wondering if maybe this focus on the future, or envy of the present enjoyed by those who are already retired, has the unintended consequence of making us miss out on the joy of the arcs of our careers.

sure, many of us may work again after we’re retired. maybe freelance work, or some part-time version of what we used to do. or just plain old fun jobs, like what we have in mind for ourselves. and we may put to use many of the skills we’ve gained through our work, like we hope to do in our volunteer and board work. but we’ll never again have a career. a directional series of jobs or positions that build on one another and represents growth and some level of reward.

especially for those of us planning to make an early exit, let’s make sure we pause sometimes to appreciate our careers. what we’ve learned, how we’ve grown, the respect we’ve earned. the opportunities we’ve enjoyed that we wouldn’t have had otherwise. the hard work we’ve put in, not just once, but again and again, over time, for long enough that we’ve changed as people along the way.

reaching the peak before pulling the ripcord

we’ve made no secret about our baller past, and the possibility that we could be retired by now if we’d reformed our ways sooner. and we’ve also made no secret about how hard our jobs are on us. i’m already 20 flights and 13 hotel nights into 2016, and mr. onl has already had multiple all-nighters. (perhaps the best description of how all-consuming it is? our christmas tree — or a desiccated shell of it, anyway — is still standing in our family room.) it’s easy to see only the bad. it’s easy to feel only the bad, when all we want to do in a weekend is catch up on sleep, even though there’s fresh snow we could be skiing. but there’s the very, very good of it, too, and not just the paychecks that are letting us save fast for early retirement. there’s the fact that, last week, i had the most senior role in a major new business pitch for the first time ever — a role i’ve wished i could have in approximately every other pitch i’ve ever been a part of. there’s the joy of knowing that that pressure didn’t make me crumple, it made me be my best self. there’s the joy of knowing that potential clients call us now, not our bosses, because we’ve built up strong reputations in our fields. there’s the joy of the same clients calling us over and over for new projects, over the course of years, because they know we’ll do good work and be fun to work with. there’s the satisfaction of knowing that we’ve built something with our careers, not just used them as a means to sock away money.

none of those joys are things we could experience if we’d peaced out of our careers as soon as we possibly could. though we’ll always feel little pangs of envy when we see 20-somethings traveling the world, or even retiring for good, we’re glad to have done it this way. even if we know that we’ll never look back from our deathbeds and say, “i wish i’d spent more time at the office,” even though we know that our careers aren’t where we draw our true inspiration and happiness from, we know there’s more to it than that. we feel proud of what we’ve accomplished, proud of what we’ve contributed to the world through our careers, proud of the relationships we’ve built with colleagues and clients, proud of how we’ve mentored those coming up behind us. so during our (we hope) many years of early retirement, followed by many years of “traditional retirement,” it makes us happy to know that we’ll have a lot to look back on with pride and a sense of real achievement.

deciding what we want out of each season of life, career included

certain careers have an intrinsic, built-in goal — a quarterback’s only real goal is to win the super bowl — but most of us have to decide for ourselves what we want to achieve in our careers, or in early retirement, or in our relationships, or in life generally. the goal is a choice, based on what we need to feel fulfilled. as for us, we haven’t cured cancer. we won’t have landed humans on mars. we won’t (yet) have written the great american novel. (haha!) but we have achieved a lot of things that we’ll always be proud of, including working our way up to the top titles at our companies short of taking over the place, and earning the respect of people we have long respected. it’s up to each of us to decide what “going out on top” looks like, and what we need to achieve first to feel that we’ve reached that peak.

what does “going out on top” mean to you in your life? or are career achievements overrated? has anyone stuck around in a career longer than you needed to, because you wanted to achieve something particular before you retired? or pulled the plug and never looked back at your career? we’d love to hear all viewpoints — please share ’em in the comments!

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42 thoughts on “Going Out on Top // Retiring at the Peak

  1. Awesome topic! To me, career achievements aren’t necessarily overrated if you truly derive happiness out of your career, but for me personally, I definitely don’t focus on achieving such-and-such role at my organization any longer, or making X amount of money, or having this-or-that title, which may be more typical goals of our current workforce.

    Honestly, I don’t know if I even established a real goal in my career.

    From the very beginning, all I wanted to do was make some money so I can supposedly “enjoy my life”. I went through day after day at work just getting by so I could leave to do something more interesting. I definitely had no idea what “going out on top” really was, and to some degree, I still don’t.

    In the NFL (or any sport, really), the championship game is THE culmination. Everybody is actively playing for the exact same end. It’s understood. It’s clear. Everybody wants Superbowl rings.

    But with our jobs (and life in general), it’s a lot more organic. Different people want different things. While some feel perfectly happy traveling the country in a van (#VanLife), others need nothing less than a 4,000 sqft mansion to call their own.

    That said, I still do believe that I will be going out on top because, quite frankly, I don’t see anything that is meaningful left to do. I’ve already had the “Director” role and thoroughly hated the responsibility of management. I’ve given presentations to 2-Star Army Generals – that was fine. I got involved in a couple different start-up companies. I’ve also just served the “cog-in-the-wheel” role, quietly getting my work done as an unimportant staff member (what I’m doing now, mainly).

    For me, there’s nothing really left to do. I’ve tried everything that I’ve wanted to try. And for me, maybe that is how I am defining “going out on top”. There wasn’t some marked achievement like a Superbowl ring. Instead, there is an absence of goals left to pursue – at least from a “professional” perspective.

    And here is where my post-retirement goals come into real focus. :)

    1. You are so totally right that there’s no obvious career goal for most of us, and for those who do aim for something for a long time, it’s often a letdown when they actually get there. I think you’re a great example, because you got the director job, and you realized it wasn’t for you. But at least you achieved that and figured that out, so you won’t spend years of your early retirement wondering, “What if I’d stuck around a little longer? What could I have been?” You know the answer, and you also know that it wasn’t bringing you happiness. That’s a great outcome! You stuck around long enough to find out, and then you figured out a better career arrangement that suited you. So in some ways, you already went out on top! :-) And now you guys are getting very close to retiring on your own terms, at a super young age, so you’re pretty much winning your own Super Bowl.

  2. Excellent post! As a Registered Nurse only two-and-a-half years into my career, my plans for ongoing career achievements have changed and will continue to evolve as time goes on. My initial goals, prior to getting on the path to FIRE, included obtaining an MBA and working my way up to the likes of Chief Nursing Officer or CEO of a medical facility. While that goal still intrigues me, I am also aware that, like you mentioned, achieving such a status is not necessarily what drives me anymore. Time with my family and having the opportunity to travel while working towards our financial independence is our goal now. Travel nursing is something that I can do with my current Bachelors degree, allowing for the combination of travel and continued work towards FIRE. Taking on additional debt while obtaining a graduate degree would likely slow this progress towards our ultimate goal. We intend to reach financial independence by the time I reach 45 (29 now) but I don’t see myself fully retiring even then; instead I intend to continue doing what is known as PRN, or as-needed, work. I will consider myself as “going out on top” when I have the achieved the freedom to walk away from my career at any time, regardless of when I ultimately choose to do so. Thank you for the thought-provoking post! Have a nice day!

    1. Thanks! You’ve put a lot of thought into your career options, and the idea of travel nursing sounds super attractive! We’ve looked into some forms of travel work, and definitely see the perks. Most of all, I love how you define “going out on top” as having the freedom to walk away, whether you actually do or not. :-)

  3. I don’t think career achievements are overrated — we put much of our best selves into them. It’s like other achievements as far as I’m concerned.

    I don’t know what my “go out on top” will look like. I have some idea of what I’d like to have happen along the way: write a book, see my children established as independent productive happy adults, hit FI and retire early despite spousal flack. Perhaps I’m far enough along in my career and life, content enough, that I don’t feel I require another “high note”.

    1. Great point — we DO put our best selves into our careers, if we’re lucky anyway. I think your “going out on top” vision sounds fantastic, encompassing both career achievements and life goals. I hope you achieve all of them!

  4. Great topic & post. It IS a wonderful thing to go out on top. Not everyone gets the chance to do so – especially due to health reasons – but I feel like I’ve been blessed to do so (and even work a one-year VICTORY lap for our charitable giving fund).

    That said, I think you hit the nail on the head when you say “Going out on top is only possible because we’ve actually earned our way to the peak.” I have worked hard over the course of my career, relish the amazing experiences I’ve had, and am happy to let it go now. I think if I had quit before I had reached the career success I’ve had I would have always wondered what I might have been able to achieve.

    1. Yeah, we’re with you. I know a few months back, we were lamenting that we didn’t figure out the FIRE equation sooner, but now we’re totally on the side of being glad that we saw our careers through to our peak years, so that we won’t have to wonder what we could have achieved, because we know the answer. Glad to know that you feel the same way!

  5. Nice topic! I like that even though this career may be fairly short compared to most, I’ve achieved a lot and gotten a lot out of it. I’m pretty content with where I am and happy where I’ve gotten, even if I don’t get “any higher”. I have “enough” responsibility, work is truly fun, and most importantly I love all the people I work with, which is huge at any job.

    I think if I’d quit any earlier, I would’ve played what if, in the sense that I wouldn’t have been tested and known that, I’m really good at my job. One of my highlights like yours was presenting to the head CEO’s of a major oil company telling them why their newly purchased $12 Billion asset wasn’t ever going to be profitable, and then defending our findings versus the Business Development guys declarations of “Major Profitability”. Oh, and they were in the room too. It was awesome! In the past I would have been really intimidated and unsure of myself, but now I know that I can perform well and even shine in those situations. Whatever comes next, I will always have this career and experience to draw on.

    1. I always love how much you convey a sense of fun in your work — we envy that! There are definitely fun aspects, but “fun” is not a top ten word either of us would use to describe our jobs or careers. So that alone is worth celebrating in your case! And earning the level of responsibility that you have is another — backed up by your CEO presentation, which sounds like it was super impressive!

  6. It certainly sounds more empowered to leave on your terms. That appeals more to me than “going out on top,” though I see where you’re coming from with that. I agree that it’s important to appreciate your career while working toward FIRE, and I think that makes the journey more bearable.

    1. Fair enough — “going out on top” might not be the best descriptor for everyone. :-) I think we’re just glad to have seen our careers through to the higher levels, so we can look back and not wonder what we would have missed by sticking around. But that’s just us!

  7. What is a Super-Bowl?

    Lol. Sometimes I honestly wish I had quit my grad program after I finished the master’s portion of it three years ago rather than staying on to finish the PhD portion. There are a variety of complicated reasons behind why I stayed on, but I think the main one was probably…inertia. Or maybe not wanting to let people down? Neither of which are fantastic reasons.

    I think it’s cool that you’re consciously choosing to appreciate the careers you’ve both worked so hard in. I think you deserve a ton of credit for staying focused and putting in so much effort for many years. It can be easy for people to be dismissive of jobs and careers as not being what life is *really* about, but, as you say, you have a lot to be proud of, and probably a lot of skills/memories/growth that will have a positive impact on your life after retirement.

    1. One day I’d love to hear more about the arc of your education. I think education is awesome, and if I’d had a little more focus when I got out of undergrad, I could have just as easily turned into a professional learner for life. (In truth, I can’t wait to take more classes after we retire, just for personal edification.) And yeah, I think this post is really about trying to pause and appreciate the career side of things, not just the frantic race to escape it all. (Though we sure do want to escape it all, and soon!) But it’s been a big chunk of our lives, and we have a lot to be proud of, and we feel super lucky and excited that we get to quit after both climbing about as high as we could expect to get AND before we do it so long that we get the life force totally beaten out of us. :-)

  8. This is a very fantastic analogy, and I wonder if Peyton ever thought that his NFL retirement would coincide so well after achieving his 2nd Super Bowl win in his career (I know there is still possibility he may not, but you are most definitely right – he’s hit his peak)! I just pictured a great storyline of yours & Mr. ONL’s career. As you are making your way up the arc in your career (not just the ladder!), you are extending your hands and allowing people with lesser experience up along the way. :) I think milestones in a career are very important – so long as you are not neglecting your family, relationships, health completely along the way. I think with you both from what I’ve read have held a very nice balance! Even if that means double digit flights & hotel stays when it’s only February of 2016 – wow! For me (only 4 years out of college), it seems like it’s been a series of little wins that have made me fulfilled. Sure, I’ve been able to accomplish some huge asks & projects from upper management that I never thought I would have ever expected to face in a lifetime. But I think what matters to me most is the trust, the relationship building, the fact that clients/customers refer you to others just like you said above that seems like the “peak.” With that type of peak – you can keep scaling it, and those loyalties & friendships will extend beyond the work place – even in your retirement!

    1. I love the visual of us helping others up behind us. I hope that’s true! :-) Hey, at a minimum, we’ll be vacating our jobs soon and making room for two other people, so that’s a good thing. :-) And though you for sure have the whole FIRE thing figured out at a MUCH younger age than we did, I hope you’ll stay in your career long enough to know what you can really do — for us, we’re super glad to have stuck around long enough to know that for sure. But it certainly sounds like you’ve achieved a ton, and built great relationships, in your years since college. I absolutely agree with you — many of those relationships will stick with us even after we leave our careers. (Honestly, it would be a lot harder to quit if we thought we couldn’t talk to our work friends anymore!)

  9. I was very unhappy and felt stuck before discovering FIRE. All of my work satisfaction seems to be tied to conquering new challenges. After spending a few years in my current position, there was little excitement left for me. I am working towards a promotion right now, which gives me a goal, but boredom dominates my “career.” I expect that it will be satisfying to look back on this season of my life for what it was and all that I accomplished, but I’m so ready to move on to different adventures. The goal that drives me right now is FIRE. If things go according to plan, I will be retiring at the peak of my career. What’s the point in staying after that, if it’s not rewarding anymore? If you already won the Superbowl ring?

    1. I agree with you — if you have another option, and you aren’t passionate about work, then there’s little point in staying past the big win. For us, we feel like we’ve hit that pinnacle, so we’re happy to exit as soon as we can. For you, have you thought about exploring other potential careers? If you’re super bored by your work, that’s got to be a drain on your psyche… maybe changing fields or companies could help you financially and help your spirit?

  10. I hope Peyton retires, its not often you see a sports figures get that opportunity to leave on top. I’m sure he made a nice nickle for dropping the beer companies name a few times during his post game interviews too.

    When I was younger I had goals or was chasing money and titles within my career, but now they are not really important to me. Having a plan for your money will do that for you. I don’t have specific goals now, more general. I want to do a good job, and have a nice work/life balance.

    1. We hope we retires, too. What a perfect way to go out, with a second ring. And I think that actually achieving work/life balance is a GREAT career goal. It’s super hard to do, and is pretty rare, so that’s an achievement worth celebrating all on its own. If you can quit after having lived with work/life balance, I say that’s for sure going out on top!

  11. I think that people who really love what they’re doing rarely choose to go out on top. My grandpa is nearly 90, and his health recently improved enough that he’s no longer in hospice. The result is that he started considering some new business ideas with my dad. Brett Favre was basically forced out of the NFL, and Michael Jordan is probably actively trying to figure out how to get back into the game.

    Going out on top sounds fun, until the person who left really just wants to get back into the game (whether the game is writing, business or sport).

    1. Haha — so true! It’s hard to let go! I think it’s the same truism that gets tossed around in FI land: make sure you retire TO something, not just FROM something. If all you know is what you’re retiring from, then it will be that much tougher to quit. I wonder if it’s possible to truly strike that balance and both appreciate what you’re retiring from, but also be super stoked about what you’re retiring to? And when we say “going out on top,” we mean that in a relative sense… we’re not Michael Jordan. ;-)

  12. A good point that you make. In all you do, it feels way better if you can stop doing what you do on your timing and terms. For me, that is going out on top. You stop when you want to stop.

    Other than that, You describe with a lot of passion how you reached certain milestones in your career. How you worked hard and made some sacrifices to get where you are now. Often, people forget this. They do not see the hard work you need to put in to achieve the next level.

    I like the definition you give of a career. Looking like that at work, makes it for me simpler to one day be FI. I might still work, but not chase a career.

  13. 20 flights in less than 2 months? That would be enough to make me want to retire ASAP too! :D

    I don’t really identify with career achievements, possibly because I’ve always worked for the same company and I’ve always known it was a temporary thing for me to get myself on more solid footing financially so that i can really figure out what I want to do and not necessarily pay attention to the dollars and cents. I feel like once you hit X career goal, then there’s Y career goal and it never ends.

    It might be that watching my parents live their lives and see how even though they have been very successful, they always found something else to spend on, and I feel like following the money path is equivalent to spinning in the hamster wheel….I don’t want that for me.

    I sometimes consider transitioning to a different career where I would have very little overhead (such as working on a cruise ship or as a tour manager on coach tours), this would more than cover current expenses and allow the stache to grow because living expenses would be so low. To combine my interest in exploring new places with an income is appealing, especially if I’m doomed to roam around alone anyway. ;)

    1. Yeah, no joke on the flights. It will be 24 by Wednesday! I think if you go into your career knowing your goal is to make it temporary, then you’re bound to approach it differently. We didn’t know that going into ours, so have taken them seriously for a long time. Neither approach is better — they’re just different. And I can definitely see the upside of doing a tourism-type job that you can do in beautiful locales, and get your room and board paid. That feels pretty darn close to living the dream!

  14. Oh man such a loaded question really. I think we all hope to go out on top in however we define it. I hope to have lots of healthy years left over whenever I decide I can live off whatever I made (and the rest I will make is just icing on the cake). But truthfully, I don’t know. I had no idea he was 39 btw. I’m not THAT much older (45) and could not imagine playing that kind of sport (even though he is qb) for that long. He is probably in pain more than we think!

    1. The pain of pro sports, especially football, has got to be crazy, right? I totally admire someone who can play the game for so long, but I also completely question his sanity. :-) And yeah, the topic is a loaded question for sure — I think we just want to make sure that we don’t glaze over the career achievements because we’re in such a frenetic race to the FI finish line! :-)

  15. I’m in the “pulled the plug and never looked back” camp, mostly because my position had deteriorated to such an extent by the time I left that I had long since lost the passion for it. It’s not the best way to go out, I would have preferred to have done so when I was jazzed rather than jaded, but it does have its upside: I was able to completely leave it behind. In the past, whether we were on vacation, I was out ill, or someone in my family was sick or even hospitalized or worse, the calls, texts and emails just kept coming. Waiting to leave until I truly no longer cared gave me the ability to no longer be available, and to make clear that I wouldn’t be changing my mind, and that decision I have yet to regret.

    1. You make such a good point about the upside of leaving after things have started going downhill: no hesitation, no second thoughts. We can’t see the future, so if things go downhill for us at work in the next year or two, we’ll have your sage wisdom to remind us that that’s not all bad!

  16. I actually thought a lot about this too, but had some completely different takes on it.

    On one hand, I look at someone like Manning, who has far more money that I could ever imagine wanting or needing and I have deep admiration for his passion to continue to compete and put his body at risk because he so obviously loves what he is doing and is engrossed by it. Another great example is a Warren Buffet who keeps working into his 70’s despite being one of the wealthiest people in the world. I compare it to going to my job that is fun, rewarding and well paying, but if I didn’t have to be there for the money, I’d be gone tomorrow (or at least after giving a respectful professional notice).

    On the other hand, I look at people like this and feel some sadness for them that they choose to do things like face 6’4″, 260 lb linebackers looking to take his head off or sit around reading and analyzing business reports when they could be choosing to do things that I perceive to be so much more rewarding and important.

    I guess we each have to decide what is important and when it is time to “move on with our lives work”. I am just fortunate to be in a position to be able to make the choice for myself at such a relatively young age.

    1. Two good takes in here! And we agree — we both admire the passion of those guys who keep going for it when they don’t have to, and we’re totally befuddled by people who keep working well beyond the point when finances are even a question. Like you, we feel fortunate to have the choice to walk away (and we’re going to do so without hesitation when the time comes!), but we’re glad we made it as far as we did, so we won’t look back and wonder what it might have been like if we’d climbed just a little higher. :-)

  17. Great topic indeed! I am right in line with your number of flights and hotel nights for 2016. When I am traveling for work, I tend to dwell on wanting to be home with my husband and dogs. Yet when I am home, it is hard for me to adjust to the slower pace. It’s almost as if I have a love/hate relationship with the fast-paced career (including the travel). I seem to be at least to some extent hard-wired for it. Regarding early retirement and “going out on top”, I feel it is a tricky scenario. When the career and travel stress really heats up, I often think I should just transition into a lower level position which would eliminate the travel and offer the option to work remote. However, the question that nags at me and keeps me from making this change is: If you are successful at what you do and enjoy it at least on some days, don’t you owe it to yourself (and maybe even to your team/industry) to stay the course and see what you are truly capable of accomplishing?

    1. Hi Mindy! I’m of two minds — I want to high five you as my fellow road warrior sister, but then I also want to give you a big hug because I know what a grind it is! I can definitely relate on the feelings when I’m away — I miss Mr. ONL and the dogs like crazy. But I’m okay with the slower pace at home, especially since work is still super fast paced. On the career front, I think you captured our feeling exactly: don’t we want to know what we could have accomplished? We’re happy that we stuck around long enough to find out, and now we’re good with the decision to let it all go. :-) I’ll be curious to know what you decide!

  18. I thought that career advancement and achievement were the same things–ascending the corporate ladder into management would have been the next obvious achievement. Now that we’re heading in a different direction with our lives and the majority of our professional lives are behind us, I will say I’ve gone out on top if I can help others with their careers, especially my co-workers who’ve just entered the workforce.

  19. Isn’t that awesome that athletes that are still going past 35 are usually over the hill and analysts talking about how they should retire? Too bad I’m a bit too short to play basketball, and not big enough to play basketball :)

    Going out on top in terms of career is a challenge for me as I’ve never been a career orientated person. I guess for me my ultimate goal would be to go out on top and retire early. Not 65 like most people. I hope to get there one day!

    1. Hearing commentators talk about how “old” athletes are reminds us a bit of when we visited the old cemetery in Boston and saw that just about everyone died by age 30 in the 1600s and 1700s… we would have been the old folks if we lived back then! :-) And hey — I think retiring early is a great career achievement all on its own!

  20. It’s so fun to go out at the top of your game…. on your own terms and after kicking butt at your job with great relationships with your colleagues, clients, referral sources, etc. Though not sure if mentioned in this post, I like your idea of getting out of the way for others to step in and do their thing. I’ve been doing that on my farewell tour but I like the visual associated with getting out of the way.

    1. I agree — I have days when I wonder if I’ve already stayed too long, but overall feel really grateful to get to go out while I feel good at what I’m doing and enjoy it! (And yes, always love the point about creating opportunity for someone else!)

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