An Update on some Failures
- Justin Doolan
- Apr 12
- 4 min read

Failure
I am starting to get more familiar with this term. All the businesses I want to start, all new things I have wanted to try. School, work, relationships, physical health or mental health. I have failed in every category one time or another. Currently I am in a stage of life where whatever I do I can’t do anything right.
My anxiety has returned more often than it was. I feel tired all of the time, I just feel like I am in a little bit of a low period of life. What is even more frustrating is I don’t think much of my anxiety is warranted. I have a very low number of responsibilities. Everything is just weighing on me and gnawing at me. Why can’t I do better? It is always a little voice pushing me further. Some of it is healthy, wanting a better life for me and my family. Other points it goes completely off the rails and I can’t get back to where I was maybe even a week ago. There are just a lot of things weighing me down. Unhealthy pressure. The pressure to never take a step back, only go forward.
There is also the added pressure of taking a leap. No idea where it could put me, it could absolutely put me behind. Clawing to come back and would make my anxiety even worse.
Or.
I could finally stick the landing. Quit my job. Live life with the added pressure and freedom of a business owner. Maybe even make more money than ever before at my job without the need of waiting several years for accreditation. It is an idea that has come and gone but what if I acted on it. Made the jump.
I have failed my physical health. I am the weakest and heaviest I have ever been. I tried to do a pullup a few days ago and I barely could do two. They were definitely not amazing form pullups either. I completed a marathon in January, but I want to get my body back to the most active it has ever been. I want to compete in a pickleball tournament, but I failed HARD when it comes to playing that.
I want my travel agent business to succeed, which I was never really set on what that needed to do, all I want is $30,000 in sales so I can get discounted vacation rates. If I can make a little cash, and even give my family and friends money to use on their vacation to make it cheaper that sounds pretty nice too. I would like to think its almost a success. I haven’t really branched out too much but I never wanted some huge brand. I took it as it was. A side hustle. A grow and work as much as you want on it but I never thought the ceiling was overly high. Which is why I want to add another side hustle to it. One I can start tomorrow and try and get clients. Clients for a service and ones that I can also plan vacations for. Throwing diversity into my day. Not just finding the costs of pretzels.
Speaking of the job, I have felt more like a failure. I have all of these dreams and ambitions, but I couldn’t pass classes in a timely manner, so I am still in an entry level job. Which can be disheartening sometimes. I can’t even create the dream business without being credited which is still far away. I feel stuck. How I should be higher. I have been extremely negative over the last few weeks.
My school has actually been improving every semester. I have been able to get far ahead of schedule which has made me feel good. When I got a 48% on my first test, less so, but I was able to come back with a B on the second test. This area feels good, I have been able to really turn my failure in this category into something more fruitful. The pace at I am going has made it easier, but I will not graduate with my bachelor’s degree until I am almost 30. My pace has been very different from my peers which is again, disheartening. But I am also going to graduate completely debt free. I will just be on the ladder slower. Which has helped me enter full-time work world, get some experience there but I never really had a college experience. I could have been in and out in four years but I was immature, I changed majors every year. I was probably the worst student you could imagine. This now leads to my transcripts looking like a webpage with all the www. On the other hand, I am debt free. Putting money towards my retirement to enjoy those great years of compound interest.
Which shows a bright side of this somewhat difficult time. My future has been set up nicely. I will continue to put more and more towards retirement, but I feel good when it comes to my finances. Which is a miracle at $20 an hour. Everything will be okay. People have different pacing in this life and my pacing was different than the rest, but I will still make it there.
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