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Underdog – Professional opportunities

I was sometimes viewed as the underdog while growing up. It was almost always the case when I was younger, and those kids that picked on me always thought that way. Anyone who I thought felt that way about me, I took that feeling of being the underdog and dug deep, used it as motivation to succeed. I think that motivation helped me, at least professionally, as I grew up.

I am also a second generation immigrant. I think that 3 of my 4 great grandparents came to the US when they were in the age range of 10-20. Both of my dad’s parents were straight from Ireland, and back then the Irish were often frowned upon, put down, destitute, had to hope just to get only the “worse” jobs available and they were not provided opportunity. Back then the Irish and Italian immigrants (among others) were the underdogs, just like many immigrants from other countries are today. While I am the grandchild of immigrants and my parents grew up in an immigrant run household maybe I also inherited some of that underdog attitude from stories passed down to me as well as there were some conversations growing up around immigration. However those who come “right off the boat” are the true underdogs and my story can’t compare to what they went through.

Throughout my life, I have always cheered for the underdog and they have always had a soft spot in my heart as I always considered myself to be one….and even today I still do think I am the underdog. In some ways that attitude may be one of my biggest assets, but it may also be one of my biggest weaknesses.

The underdog mindset is great for me as it gives me the drive. It helped me to be very successful professionally and it helped me to be a top financially and retire, but the drive as well as attitude of being an underdog also makes it so hard for me to enjoy that professional and financial success as much as I should. As the attitude is hard to turn off. It is hard to stop striving to be better, to prove myself professionally, and to be one of the best at what I do. It is an internal battle I have of trying to control the drive vs. enjoy the results of it!

Taking the mindset of being the underdog, and using it as a driving force in my professional life I think has helped me greatly. However I have had mixed results when rooting for the underdog in other aspects of my life.

There have been some stock investments I made, especially earlier in my life, in which I invested in the mid-tier or smaller companies instead of leaders in an industry. Of course I did my research, thought they could make up ground with the leaders, and pull ahead. But generally those investment in the underdog companies did not work out for me.

I was burned a few times in the corporate world as well. There were some chances I took on people who maybe were considered the underdog. A couple people I promoted and they did not work out in their new roles, and there were some projects I would sometimes allocate to someone who may have been thought of as an underdog but they struggled.

But there have also been many successes in the corporate world as well. It was great to be able to promote a few people who may not have looked like stars on paper. I was able to give them roles that gave them more responsibility and money. They often did not have the best college degrees, were not kissing up to people, did not have the best “background” or maybe experience, and were often looked at my peers as the underdogs. But they were driven and hungry, and to see those “underdogs” succeed in their new roles was incredible.

I remember the two women who took on managerial roles. Both of them did not have the “top” college degrees, were on the quiet side and just came to work everyday and were great at the jobs. They were super talented and smart (probably smarter than me), but they never had the top tier degrees/experience and they never wanted the focus or attention to be put on them. But I saw that underdog approach in them and gave them an opportunity and they ran with it. There was also an older male who many thought was “washed up”, the immigrant from India who I promoted and the contractor from Pakistan who I gave a full time positions too. There were some other successes too. All of them were not perfect on paper, but they fit the bill of being underdogs and used that drive to succeed in their new roles.

While they succeeded in their roles and professional life based on their own ability, talent and drive, and they would have done great without me, just maybe I made it happen a little earlier for them by giving them the opportunity. As an underdog will more often than not be successful no matter what they do. So there were some disappointments (and I probably did not do a good enough job in preparing them so I take some responsibility for that), but the successes were something to see.

I have also talked about mentoring through Score. That has been some experience! Some people who go through SCORE are so entitled and think starting a business is simple or easy, and they are so unprepared. Even coming to the SCORE office with no preparation done. But sometimes I mentored the SCORE client who was unsure, not confident, “eccentric”, knew they had work to do, and were committed to it. They had the underdog attitude that they were entitled to nothing. But they had the desire, motivation, and drive to succeed. I love when I get to work with those SCORE clients.

I have always cheered for the underdog, and hoped for the success, I think because of my background. I have always cheered for the kid from a single parent, low income background or the student from a school in maybe an inner city in which the school was not provided the funding to help all the kids there. I wanted the underdog single mom raising kids and paying the bills on her own to be successful, or the immigrant that faces challenges in a new country. Or the student who was bullied in school, the person who took on major risk in starting a business, or the older worker going back to school for a new skill…they are often the underdogs too, and I want them to be great as well.

As we reported in an article here, women (regardless of their race) are not paid the same as men or provided the same opportunity as males. As the post indicated, it is a shame that women are not treated equally in the workplace. Coming from a single mom, for women not to be giving the same opportunity/income as men is a personal topic for me that I take to heart, as I will never forget how challenging it was for my mom to raise me and her kids. She struggled to pay the bills, feed us, and worked so hard. She was a true underdog

It is terrible that women are still often not given the same compensation and “rank”. They should not be paid less and they should be given every opportunity to hit those top corporate roles, political positions, and whatever else they desire. Being almost entirely raised by a single mom and closer to my sisters, this is a personal topic to me…equality for those women who are the underdogs.

When I hear about other people who come from rough backgrounds, low income families, or maybe abusive situations or difficult parents I want to try to help them hit their goals. When I hear about the kid with drive and determination, who came from a single parent household and who has the underdog attitude, I want them to succeed. When an immigrant, or child/grandchild of one has that drive, that is a great thing. Whether it is personal, financial, career, or whatever, I want the underdog to do well no matter where they came from and their story.

It is hard for me to get away from that, in trying to support someone or even an underdog company. While a part of my would like to stop rooting for the underdog, a part of me I think will always do it and fall into that trap. As I think, at the end of the day, I am a hopeful person and I want them to succeed.


Jon McNamara is the CEO of needhelppayingbills.com, a company that he started in 2008 and that specializes in helping low income families as well as those who are in a financial hardship. He also found NHPB LLC, a company committed to helping the less fortunate. Jon and his team also provide free financial advice to help people learn about as well as manage their money. Every piece of content on this website has been reviewed by him before publishing and many of the articles he has personally written. Jon is the leading author for needhelppayingbils.

3 thoughts on “Underdog – Professional opportunities

  • January 28, 2019 at 7:20 pm

    Dear Jon
    I’m a single mom of three beautiful hard working girls from South Carolina. We are really struggling. I lost my job and finding another full time professional job opportunity in these difficult times is hard. I even sold my car to keep us afloat.
    The girls are about to get expelled at school due to lack of funding and non payment. I can’t pay for them and they are very intelligent and hard working.
    I am currently studying for a professional job and at times I don’t get to class due to not having money for transport. At times we go to bed hungry due to lack of food. We are the ultimate underdogs and everyone gives up on us.
    I’m am asking the organization to help me find a job and help me pay for my girls . They deserve what I can’t get them. Actually any kind of help will be a great blessing.
    Thank you for taking your time reading my letter.
    Yours sincerely

  • March 25, 2019 at 4:17 am

    Everyone loves the underdog. I too often feel like one, and want to prove myself that I can get better jobs, pay the bills, care for kids on. It is so hard. I love this quote and have note on my bedstand. “If you’re an underdog, mentally disabled, physically disabled, if you don’t fit in, if you’re not as pretty as the others, you can still be a hero.”

  • May 16, 2019 at 12:54 pm

    Growing up with little money and education, I think I was underdog by default. then I started my first real job, and got my opportunity, and then I quickly got promoted had more opportunity and work to do than I could get done, plus more money. There’s a lot of truth to being an underdog. Always run like someone is out to take your job or opportunity. Complacency is a killer.


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