Four Ways to Be Strategic About Losing

Updated: Apr 21

You don't have to be a follower of the Royal family to have been forced to watch it undergo signs of unravel in the media. I certainly wasn't.


What is intriguing about the whole drama though, is that normal everyday families go through the very same thing all around the world, including America.



Samir Hussein | Getty Images

In watching some of the highlights of Meghan and Harry's interview with Oprah that recently aired on March 7, 2021, I got to thinking about how often in life, we are forced to lose in order to win, or to be set free.


In Meghan and Harry's case, they needed to lose their original lifestyles. For her it was career and Constitutional freedom. For him it was family, tradition, and financial security.


For some of us, it is giving up a job that holds us back in some way or giving up a marriage that turns out to be damaging. Maybe we have had to give up a relationship with a parent or mentor that we were always close to. Sometimes it is being forced to pivot a dream.


The truth is that the way we are taught to lose or to adapt as we are growing children has a huge impact upon how we are able to process loss as adults. Even as children we develop our own personalities and some of us are more compassionate or competitive or relaxed than others.


People who grow up feeling pressure to win, either due to their parents enforcing those beliefs or by watching parents struggle and the children believe it is their job to fix it, sometimes cannot handle misfortune.





Much like Meghan and Harry described, it is natural for most of us to want to shield others from the truth of falling apart.


Sometimes we do it because we don't want to answer questions or explain ourselves. Sometimes we aren't sure who we can trust with the information. Maybe we feel ashamed or embarrassed because of our own background. Maybe we are too concerned with trying to fix it before emotionally confronting it.


Madam Uplift is always circling back to the idea of failure and why it should be destigmatized. Everyone is going to experience it. Everyone will experience disappointment or embarrassment. There are healthy ways that we can keep on keeping on and reversing those patterns.


Losing is almost a requirement in becoming a winner. Michael Jordan was a loser long before he was a 6 time champion. Floyd Mayweather Jr. who never lost a professional fight as a boxer did rack up a few losses as an amateur.


So how you develop an undefeatable attitude even when you've actually experienced a few defeats? It isn't simple but it is critical:


Here. We. Go!



Always remember the world is set upon balance.


Nothing will ever be all good or all bad. Although at times you will feel victimized, or may in fact be victimized, remember that life is never fair or fully kind to everyone else either.


Think of the millions of other people who couldn't pay their rent, got sick, lost loved ones, aren't where they want to be, or are somehow in the same fight you are.


The good news is that over time, if you stick around, at some point that circumstance, pain, or feeling of solitude will be lifted. I guarantee that you can think of at least five things that felt un-survivable that you have survived.


You cannot fully grasp good without understanding bad. Some people do great with money but are horrible at relationships. Some people are mentally or creatively gifted but do not physically perform well with their bodies. Some people are great at producing things but struggle with marketing them.


There is an upside to struggling when we decide to see past it for what else it could become. In the beginning of crisis, the last thing any of us think about is what is the upside of this issue. We need our time to grieve and process negative feelings.


However, once we have taken that time, we need to be able to seek clarity and remember that we have to deal with both the positive and negative sides of events.




Always anticipate change is coming.


I admit it: there are some situations that drag on for so long that it seems like it will never end. This is especially problematic when it comes to those who are enduring some gorm of isolation or abuse from another, long term financial misfortune, or a long term or chronic illness.


In the Meghan and Harry interview, for them it had taken four years of feeling that the media had attacked them with no support from their family before they could bear no more. Meghan shared that she saw it repeatedly happening for the rest of her life if action were not taken. It is possible that things would have gotten better but at the time there was no evidence.


Sometimes the evidence takes a long time to appear whether it confirms the good or confirms the bad. One thing I do know for sure is that few things in this life that come against us are permanent. Even the things that are permanent can often be used as a tool to sharpen or improve something else.


Having the exact same problem or exact same comfort is almost always going to change. We may have problems with money but in different ways each time. We may love our jobs but the title, responsibility, or company may change. How well we are able to get along with our children or partners will fluctuate.


It doesn't mean that all is lost every time. There would be no point to go on living if we attained everything all at once and then things stopped happening. People get tired of hearing that they can find ways to make their misfortunes useful, but it has become somewhat necessary.


Most relief organizations or projects are born from good people who decide that bad things happening won't be the end of the story. If we can continue to believe the story is not over, until it is undeniable that it is, whatever we are in has a chance of change.


Protect Your Mental Health Above All Else


In this world there will always be someone who wants something from us and within their designated time frame. If it isn't work related or family related it could be school related or finance related. Sometimes the demand may even come from ourselves.


However, there will be times that we are not available to give of ourselves without a pause or time to reset or to think things through. There will be times to delay a response or we need to push ourselves to speak up about something that isn't okay.




There will be times that it is important to say no as well as times that it is important to say yes. Not only do we need to give ourselves permission for that but we need to extend that grace to others as well.


People who feel emotionally or spiritually depleted or trapped begin to get ideas about hurting themselves or hurting others. Those thoughts and feelings don't even need to be rational, and often aren't.


It is too easy to feel like a loser when life isn't going in the direction we believed it would go. In Meghan and Harry's interview, Meghan confessed that she was bothered by being silenced in her new working role as a Duchess when she had previously been all about women's rights.


Even more shocking were the detailed revelations about moments of psychological breakdown when in front of the public and alone, to the point of suicide contemplation.


There are people who snap and hurt their children,or their parents or coworkers, or strangers in a crowd. Mainly due to not taking the time or not yet being able to get a handle on the pressures that we face as people each day.


How can we move forward as both leaders and as people obligated to others in causing and taking on less pressure? Is it the way that we think everything is critical or that everything HAS to be done? Is it appreciation for ourselves and who we have?




Consider ways to understand when mental struggle is happening and when sometimes pressing pause, damn the consequences, has to happen.


Get Involved In Your Own Life


In order for anyone to assist someone in winning there must already be some form of action taking place. The saying you can't help those who don't want to be helped remains true because it's almost never proven wrong.


Depression and anger have the greatest chances of setting in when we believe we have no power over outcomes or there is nothing good to look forward to. These feelings can grow deeper with long periods of isolation and lack of support from others.


When we find ourselves feeling trapped or useless, we will not always feel like being active but we have to try, even while feeling it. There have been many times I have felt overwhelmed as a parent so I would look up activities for me and my little one for my next free day to get us outdoors.


Sometimes simple things like movie night at a friend's house or hosting dinner or sitting at the park can help inspire thoughts of a happy future. I did things like this while in-between jobs in New York City to battle moments of depression.




Perhaps getting excited about helping others can provide renewed purpose. When my FT job had to shut down due to Covid from March 2020 until late May 2020, Madam Uplift was born, and so was the drive to look for volunteer opportunities and take certification courses online.


When you are feeling behind or that you are stacking losses, it is the best time to think about the areas where you can win or create a shift. For Meghan and Harry, it meant fully creating distance from what they felt was a toxic environment. Perhaps you feel this way about your marriage, where you live, or your school.


If you do not feel like you are living the life you want to live, start making efforts to reach out to others who are and ask how you can help. Or perhaps you can create your own environment and bring others along so that you need no one else's permission to be who you want to be.


In order to win we must be strategic when we are losing. We are to take those moments to pause and then ask ourselves what we can do. The pressures of life will not fully stop as long as we are living, but while we are living, those pressures can be balanced with triumphs.


No one escapes without suffering some losses so the key is to not settle in them and take them too personally.


Which suggestion for coping with loss is your favorite and who is your personal inspiration of a "loser" turned winner?

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