Cutting Your Losses: Why I’m Losing in Order to Win

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Let me tell you why I’m cutting my losses, losing in order to win, and how cutting your losses can sometimes be the best thing.

This post was originally published in 2014. It has since been updated for accuracy of links and content.

It All Started With an Accident

As you may have read in my post about the cost of full-time travel in 2013, it was a tragedy-filled and expensive year for me. One of the main reasons for this was a head-on collision that I survived (my (ex)partner and I were riding our scooter, and were hit head-on by an SUV) in February 2013. It turned my life and travels upside down, and ultimately led to the demise of my relationship and life in Grenada.

It Continued With Insurance

When we got into the accident, we only had third party liability insurance on the scooter. That meant we had no coverage for this accident, for which we were not at fault. Our recourse to get money (for medical bills, loss of the scooter, loss of income, and other damages) was through the other driver’s third party liability insurance. We knew this would be an uphill battle, and it was. Is. (Was).

Almost Two Years Later…

We haven’t seen a penny. (Or rather, I haven’t. I can’t speak for my ex, but I believe he’s still fighting for compensation as well). The insurance company has done everything possible to delay and negate our claims – as insurance companies do when facing a significant claim. They’ve played every game in the book to refuse certain expenses, fight others, and blatantly ignore the rest.

I no longer live in Grenada, and have been at the mercy of a lawyer (of questionable quality) to advocate on my behalf – more strikes against me.

The Settlement Insult

The insurance company did make a settlement offer: of less than $2,000, which doesn’t even cover the cost of the totalled scooter, much less my medical expenses, lost income (for which I submitted proof), and the myriad of intangible costs of this life-changing accident. With my luck if I had accepted that claim, the lawyer would have taken most of it as his fee.

Instead, I countered with a reiteration of expenses and receipts and yet more proof of why everything is legitimate. They said “no thanks”. With no counter offer, nothing. Just, no thanks.

Lawyer Problems

The next problem arose when my lovely lawyer informed me that although he was able to negotiate a potential settlement, he was unable to take this matter to court (which was the next step), as he has a potential conflict of interest since he personally uses the insurance company in question.

When I finally located a different lawyer through an international network and lawyer-friend in Canada, I was informed that I would be required to fork out thousands of dollars in a retainer fee to use them, and that there was no guarantee that I would recover the money I paid them even if I won the court case.

Cutting my Losses

Anybody with a law degree reading this next bit is going to cringe: I’ve decided it’s time to cut my losses. I’m going to do exactly what the insurance company wants me to do, which is to walk away.

Although the retainer required by the new lawyer was the impetus for this decision, it runs deeper than that. Since the accident, I’ve invested a huge amount of time, money, and energy in everything from physical and emotional recovery, to the ridiculously ugly claims/settlement process itself. All this energy has been incredibly negative, and has not helped me move forward with my life.

Going to court is no guarantee that I’ll recoup any of this money, and my time and energy spent is gone forever. In fact in order to go to court, I’ll likely have to return to Grenada at great (further) expense – financial and otherwise, and through what will surely be more games played and delayed court dates, even more expense and time than anticipated – for which there is no guarantee of compensation for any of it.

I Lose, They Win, and I Win

I wrestled with this decision long and hard. On the principal of the matter, it ires me to no end that I’m letting them win by not fighting this claim further. I’m losing, and they’re winning.

But in letting go of this battle, I also win. I win my life back.

I’ve been in a sort of stasis for too long, waiting for compensation (dare I say even hoping for a life-changing settlement), which I’ve realized is not going to happen. Whatever settlement I could have received wouldn’t make or break me financially, but the process of getting there could do so emotionally and physically.

You know what? Keep the money. I’m getting on with my life.

Have you Ever Lost to Win?

I’m not looking for legal advice, so please – I don’t need to be told what a horrible decision I’m making from a legal standpoint. I’m aware.

Instead, I’ve chosen to bear this personal story for the world to see, to demonstrate that sometimes, we don’t have to win a battle, even if we know we’re in the right. Sometimes, winning is taking the high road, cutting our losses, walking away, and moving on.

Since making this decision, I feel better. My demeanour is lighter, and I smile more. I’ve turned the final page and closed the book on my relationship, and now I’m free to create a new life for myself. And you know what? It feels good.

Have you ever lost something, to win in life?

This is one of a few serious challenges I’ve had in my 12+ year full-time travel career. Natural disasters, diseases, more breakups than I’d care to admit to…’s all here.

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40 thoughts on “Cutting Your Losses: Why I’m Losing in Order to Win”

  1. Cutting your losses is sometimes necessary & often the hardest thing to do. Being able to seeing what this was really costing you is a gift.
    Time is the most valuable thing you have but most don’t realize that until it’s a bit late in the game.

    Enjoy the day!

    • It seems this topic has not been commented on for quite a long time, but as I just read your article, I will give you my much less tramatic story (to say the least)

      I have been debating whether or not to fight with a company who owes me money, slightly under $1000, for my fitness services with their elderly clients. (It is a rehabilitation hospital).

      They had always been slow paying me, but suddenly the checks just stopped. I asked them what was happening (but I kept serving their clientele), and I was given a corporate number. The corporate number would have no actual person answering the phone, but she left a detailed message for the answering service “If you are a vendor, please deal directly with your local company, because they do their own invoicing and payments”

      This is a big company! I cut their service off, but quite nicely, saying that I would resume service when accounts were up to date.

      They won’t respond at all. After years of service, it seems they deliberately were taking my services, knowing they would be stiffing me.

      So recently I began to notice, that I was angry and negative, and this is the beginning of the year. And I wondered…am I doing the right thing? Because it means I would have to keep calling them, and begin to record details, take names, go to small claims court, etc. And I want to grow my business this year. Is this the right path to growth?

      I just want you to know that your blog post nailed it. I’m going to walk away. If they pay me, great, of course. But in my heart, I’m going to walk away, knowing I gave some elderly people some great times, and helped them move and smile a little.

      And I will take my lessons, and not overextend credit, nor my trusting soul. And I will meet better clients, and I will bring in 10x what this unethical company owed me, and have joy in my heart.

      • Hi Monica,
        I’m so sorry that a great working relationship for years ended on such a sad note. It’s not fair.
        The mis-management of accounts in large companies baffles me – and it happens all the time.
        More than once (last year alone), I wrote articles for major publications and companies, who uncharacteristically delayed my payments, by up to four months. Four months! I had to follow up many times (and in one case I continued to write more articles as per the contract even though I worried I may never get paid).
        I’m pleased to report that eventually I did get paid (each said they had a shakeup in accounts payable and my information had been lost).
        But I’ve had it go the other way too, where an article I wrote that got published (in a major magazine!) was never compensated.
        I hope that you do continue to follow up and that you eventually get paid. In the meantime I think it’s reasonable that you have suspended your services until your account with them is up to date.

  2. Hi Nora. I have been through a similar situation, although mine was an employment issue instead of an accident. It was a messy situation… one that even employment lawyers wouldnt touch wihout encountering serious heafty fees. I knew I had been an unfortunate victim caught in the crossfire of a shareholder struggle but I knew they were (seriously) in the wrong so I fought. Without a lawyer. Collecting any knowledge I could from govt. websites. In the end… I got as far as mediation. I got an offer. It was almost half what my bottom line was walking into the meeting and possobly not even half of what I would have gotten if I won in court. But in the end I took the offer and walked… made to feel dissapointed with my choice. But the issue had already consumed 6 months of my life and I was tired of fighting and the negativity that it brought. To go on fighting would have meant many more months of self representation… my name getting dragged through the courts and black marks against me for future employment. I decided it wasnt worth it. I cried (due to dissapointment and relief that it was over) and then got on with my life, a spring in my step as I could leave it behind. You made the right choice. Holding out for a slightly potential life changing reparation payment is not worth not being able to go on with your life in the mean time.

    • Hi Jadlebug,
      I’m sorry you had such a terrible struggle. It’s such a tough call in these matters – knowing when to walk away, and what to accept. In the end though, it looks like you, also, made the right decision. Cheers to that!

  3. I agree with you…you let go of that negative energy+future delays and cost and moved forward. I CANNOT believe how insurance companies can do this..maybe a search for an ethical company in Canada and International would be good.. Is there any? A story on that… Sending you tons of positive energy !

    • Thanks, Lynn!
      It’s the job of an insurance company to limit their liabilities and NOT pay out, but they can be very sneaky and underhanded in their approach. I’m reminded of the movie Memento (great movie, by the way), but one in which the main character who used to work in insurance had to make some very sleazy decisions.
      I’ve had to make claims on other types of insurance, and I know what a mess it can be. This however, was a whole new ball of wax for me, and an experience I don’t care to repeat.

  4. Ekk, I love travelling but I’m well aware if something goes wrong, fighting a legal battle when you live abroad will be very difficult, especially if the country has a questionable legal system. Nora I recall reading one of your articles on insurance in which you said you had ex pat insurance instead of travel insurance, if you had travel insurance would the travel insurance usually compensate you for situations like this?

    • Hi Leo,
      That’s a tough call. Many of the expenses I incurred – or rather lost due to the accident, such as income and quality of life – weren’t direct medical expenses, which neither travel nor expat insurance policies would normally cover (and my deductible was high enough that I would have gotten very little if any compensation from them for the medical stuff). They would have referred me down the route I went, since it was an auto liability situation.

  5. Hey Nora, thanks for articulating this. I love the perspective you share on getting your life back. I can only imagine the internal struggle of all this. Many great wishes on stepping forward from this impactful event on your life.

    • Thanks, Tiffany! It feels good to move forward, even if it is slightly broker than before the accident! Ha ha.

  6. I’m a lawyer in the US, this is typical for insurers here as well. Sometimes reclaiming your life is the best win you can get. Best of luck and know that to them it wasn’t personal, they are required to fight to the end for every penny as part of their job, and for the adjusters I work with, most hate having to do so. Happy travels!

    • Hi Lapine,
      Thank you for weighing in – especially as a lawyer! (I have a lawyer friend in Canada whose blood is boiling that I’ve not pursued this claim since I’ve essentially played into their hands). I don’t take it personally per se, but I’m still disgusted by the injustice of it all.

  7. Hi Nora, I think it’s always the best decision to consider your mental health first! After a couple of experiences with insurance companies (once for a phone, once for a car, both no problems), I found that the car premiums went up so high, it would have been cheaper not to claim. Since then, I rarely take out insurance (occasionally to some countries when travelling) and I save the insurance money instead.

    • Hi Sarah,
      Yes, I try to make insurance claims as infrequently as possible (hence why I didn’t bother my expat insurance company about the accident), since as you observed, not only can it be a headache, but premiums can go up.
      I’ve also recently dropped my property insurance policy to save my pennies and the possible aggravation of having to make a claim.

  8. Hi Nora,

    Funnily enough I used to work for an insurance company (nothing to do with insurance I hasten to add)and I ended up suing my boss and his boss (both nasty pieces of work) and with the help of a lawyer I got 70% of what was coming to me . For the last remaining 30%, the knifes were out and I thought, ‘I’m unfit for human consumption’ and I walked . The icing on the cake came a few months later when they were both found out and got rid off.

    And I also got a call would I like to come back and clean up the mess . I can’t remember my answer but it can’t have have been polite 🙂

    • Hey Dick,
      It’s too bad that you had such a nasty experience from within an insurance company. I don’t generally hold the people working for insurance companies responsible for insurance-yuckiness, but as you’ve demonstrated, I guess being in that industry for too long can get under your skin in unsavoury ways.
      Glad you got some icing on the cake though! 😉

  9. Wow, Nora. Thanks so much for sharing. I’m so sorry you had to go through all that. And I agree – sometimes cutting losses is the best thing. I’ve had to do it a few times (in far smaller increments of money): when I left a horrible housing situation early and lost half a month’s rent in the process, when I chose not to fight an unfair (inaccurate) driving ticket, when I bought an incredibly expensive last-minute plane ticket because of some immigration troubles.

    It’s upsetting when you lose so much over something that wasn’t your fault at all. But your energy and mental well being are worth taking some losses sometimes.

    I hope things take a turn for the better this year.

    • Hi Gigi,
      Thanks! Yes, last year (2013) I had a few other financial “incidents” that were completely unfair – your recount of buying a last minute plane ticket reminded my of my own last-minute international routings to get back to Canada to get a new passport when mine was stolen in a country with no Canadian embassy. That was a $10,000 fiasco all in all:

      But rest assured, 2014 has turned out to be much better, especially now that I’ve closed the final chapter on this ugly accident from 2013.

  10. I think you’ve made the right decision Nora, even though it is totally unfair! I have had just the very minor issue of claiming for my lost baggage this year and even that has been an absolute pain, with the airline playing off against the insurance company and each of them requiring different kinds of info and … well, it goes on and on, and is over just a couple of thousand dollars and basic non-essential belongings. I can only begin to imagine your version which would be about a lot more money, a lot more emotional distress and involvement, etc etc – I think walking away and forgetting about it all is an excellent choice. It’s not fair at all but it will leave you happier, and really, that’s the most important thing. It sucks though and I’m sorry for your bad experience! xxx

  11. Hi Nora…
    Despite the sad situation I’m really glad that you it turned it into a positive lesson.
    Giving up of our rights and especially our money is not easy at all, but sometimes it is worthy! I had a similar situation, when I was living in Brazil (12 years ago), My mom was battling in court against a big Construction Company and the process sucked all her energy. Year after year they found ways to postpone the dates, the payments. They even lost the papers… Summing up, my mum passed way two years ago and till now we never got the money we should receive.
    I just gave up of it… The money would be great for me, especially to keep our travel dream, but I promised to my mom and to myself that I will not spend my energy and my happiness on it.
    Wish you all the best!!! Safe travels!

    • Hi Natalie,
      Wow – what a terrible situation you yourself have had to deal with as well. But indeed – I’m glad you came to the same conclusion as myself – it’s not worth the energy and stress, which you could apply to finding other ways to keep your travel dream alive, and honour your Mum as well.
      Happy travels!

  12. I think you did the right thing Nora…there is a time for a fight, but then you have to re-evaluate for what is best for you. Take care of yourself first and foremost!

  13. Dear Nora,

    I just read about your awful scooter accident. I am sure glad that you have moved on with your life. I wish you all the very best to and thank you VERY MUCH for your great website and great suggestions and tips. Please keep safe and healthy.

    • Hi Jacqueline,
      Thank you so much for your kind words and support! Life happens while we’re busy making plans, and if I take the right attitude and approach, I can even be grateful for the accident. Que sera sera!

  14. Hi Nora,

    I’m so sorry to hear of your ordeal. But I was relieved to read that you came to the conviction of letting it go. I would not think it as a “loss” although it may feel like it for a short duration. But hindsight is always 20/20 and you now realize that it was not worth letting it steal away your joy. I too have had many losses in my life journey and it sure took time to get over it, heal from it and learn from each situation. “The longer I focus on my depression, the longer my depression lasts.” We must not put off till tomorrow, decisions that can be made today. I’m sure now that you have that “monkey” off your back, you feel a lot lighter.
    I’ve often wondered if it’s worth having travel insurance, as the onus is on us to prove the losses we incurred. Insurance companies will do whatever it takes to gives us the run-around and rarely have I heard of an insurance company being pleasant to deal with.
    One thing I strive to do regularly is to “count my blessings” whenever life gets me down or issues start weighing on me. It helps me regain the proper perspective and realize I have so much to be thankful for, despite whatever circumstance or dilemma I am facing. I’m glad you’re in one piece and I hope you have recovered from your ordeal, physically, emotionally and spiritually. All the best as you get back on the road of life.

    • Thank you for the kind words, RK! Indeed, to have the monkey off my back is a great blessing.
      With regards to travel insurance, I’m still a devout carrier thereof. These battles I had here weren’t with my own insurance company, but rather with trying to claim money on the other driver’s 3rd party liability insurance. That’s inherently a more difficult thing to accomplish.
      I’ve had to make a few medical claims with travel insurance over the years, and while you’re right in that insurance companies are rarely easy or pleasant to deal with, just one serious illness or accident in the wrong place where the cost of medical care is high (or even worse, if you need to be evacuated to a place with proper care) – can bankrupt you. So I structure my travel insurance to have a high deductible (to keep my premiums low), and it’s in reserve in case of a major medical incident.

  15. I didn’t read through all the comments, so forgive me if this is a repeated question but wondered if there was anything you could do upfront (before the accident) to protect yourself? Meaning, for all of us who travel, is there a way to protect onself from this when if an accident occurs – besides getting travel insurance which I do? of course you do the best you can and cannot anticipate what others do, and always drive defensively, watching out. But?

    • Hi Mischa,
      With regards to this instance – and many instances in life – there wasn’t much I could have done to protect myself up front. There’s only so much you can do in life to avoid the unexpected. In the end, you could swathe yourself in cotton balls and never leave the house….but then again a truck might drive through your window and into your living room!
      So I just live life as I wish, taking calculated risks (like driving in traffic and assuming others on the road will obey the rules), and I just have to accept the circumstances that are dealt to me (such as this accident) as a blessing in some way.

  16. Nora:

    Money is usually replaceable but you can never regain lost time or replace the unhappy days. Glad to hear that you have weathered that storm and you are now in a happier place.

    I am just surprised that you did not name the insurance company who put you through the wringer – by calling them out by name you could perhaps cause them enough loss of business to “compensate” for the money that they should have paid to you. I have been insured for many years by AMICA and they have never questioned the very few claims I have had – they even went as far to call me after riding out a hurricane to determine whether I suffered any losses and when I told them that my only loss was a freezer full of food that I was not really worried about, they turned right around and offered me a very generous amount (several $100’s) considering I had not even made a claim for that loss.

    As such I never fail to recommend them. On the other hand if they had treated me badly I would be equally vocal about their short comings to warn others to steer clear

    • Hi Simon,
      Great suggestion, but with 3 problems:
      1) The insurance company in question wasn’t mine – it was the other driver’s insurance company, through whom I was trying to receive compensation on their 3rd party liability. My personal insurance was only 3rd party liability, and although they were kind and helpful, without having comprehensive insurance, they weren’t having to advocate on my behalf.
      2) It’s an insurance company in Grenada…which in terms of my broadcasting my story to the world, will be fairly irrelevant. Many Grenadians aren’t even online.
      3) I don’t remember the name of the insurance company – which I’ve (purposely) blocked out of my memory!

  17. I’m so sorry Nora. You certainly deserve so much better.

    The law is quite unfair unless you have money. That is stating the obvious.

    I gave up all my income (and then some) to divorce my first wife and lost custody of my first two kids (whom I love very much, but a relationship with them was impossible due to her psychotic controlling behavior developed over time), to finalize a divorce.

    I was free at last! More than three years and a lot of fantastic times later, I remarried a wonderful woman and could not have a better relationship (unless we were living in Italy, as I want to, and we will).

    In addition, the ex soon begged me to see the kids more and more as she could not handle the absolute control…

    Gave up much, but it turned out so much better.

    I am sure, given your incredible energy and direction, that such will be the case for you–it already appears to be!

    Best wishes, as always,


    • Thank you so much for your support and friendship, Greg!
      I think often in our lives, in order to truly move on we have to cut our losses in one way or another. But in the end – as it seems for both of us – it has served us well! 🙂

  18. I understand the need to move on and reclaim some emotional stability. I had a recent experience with an airline. My family and I were about to take a 3 week trip to Europe (which we had spent 2 years saving for) when just four days before we were to leave my husband had a near heart attack (37 year old and healthy, so very unexpected) and then 2 days after that my dad suddenly passed away at age 66, also very uunexpected. When I called the airline to explain they gave me the run around for about a month until finally settling on that they couldn’t do anything for us and therefore we lost all the money spent on airfare. I wanted to keep fighting but it was taking such an emotional toll on myself during a time I was both caring for my husband and greiving my father. I had to let it go. It still makes me angry when I think about it and every once in awhile someone will tell me I should keep trying to fight it but I need to put it behind me. I assume your experience with the theft falls along this line too. On the bright side, now a year later we are finally taking that trip again and we added a week (because we deserve it damnit!) So soon we leave for a month in Germany. Life gives us some tough lesson sometimes but they have to be experienced to be learned.

    • Hi Sunny,
      I’m sorry you had such a tough time; I cringe to think that insurance companies capitalize on our suffering by knowing that when we need the money the most (and have the least energy and ability to fight for it), they don’t make it easy for us. That’s why I’ve dropped a few other insurance policies (like property insurance) that I know is difficult to claim for, and I’m saving myself the time and aggravation (and money on premiums) now.

  19. This is a great topic. I agree, moving on, letting go, is the best course of action. I have done it many times, for small and large situations. The big ones:
    -divorce settlement, made him an offer lower than half, and he took it, and never saw him again (2 years). Invested that money and it doubled many times over over the years
    -downsized after 20 years of successful career, tried to negotiate a better lump sum and better pension deal, but gave in quickly to move on (2 weeks). The lost pension I was concerned about is now trivial compared with my annual income
    -caught in a CRA situation not intended to apply to me but officials were stubborn, I ended up paying a big sum instead of getting a much bigger refund (2 years). I was broke at the time, and used credit to pay up, but it made little difference in the long run.
    All good decisions because amounts that seemed huge at the time, are now not relevant because I now have far bigger income and much higher net worth because I focussed on investments.
    Now I might fighter harder and longer because it doesn’t matter, but then it mattered so the stress and time was far too great a price.
    There is a famous book called How to Find Freedom in an Unfree World by Harry Browne (full text online) that taught me this lesson many years ago — in short, pay the price and move on to better things.

    • Hi Dunny,
      Wise words! And yes, in matters large and small, we seem to constantly have the choice as to whether to fight or to move on, and it’s different every time. At least it keeps things interesting! 🙂

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