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What if you Could Take a Do-Over on your Career?

Last updated by on March 26, 2014

Do you ever wonder “what if” when it comes to your career choices and how fate has played out?

Looking back over my career, I would not say it has been an ideal fit to my personality and interests. But for comparative purposes, I think I’ve had it pretty darn good in my career and with this here little blog.

Still, I occasionally wonder, “what if I had chosen differently or fate had dealt me a slightly different hand?”

What if I hadn’t pursued the marketing degree, and instead chose one of the dozens of other degrees I considered in my confused college years?

What if I had decided not to get a degree at all?

career changeWhat if I hadn’t accepted my first job offer? Or 2nd or 3rd jobs after graduating? Or took different jobs? Or had never been offered at all?

I don’t obsess over it, but it does grab my imagination at times.

In a casual friend/co-worker setting, I think most would say they would do something similar to what they are doing right now, if put on the spot. Confirmation bias (who wants to admit they jacked things up?). However, if asked the same question on their deathbed?

I’m a bit of a realist when it comes to career change. I have seen people do it with success (including my wife, who left landscape architecture behind for a nursing career) and I’ve seen others with less successful results. Whether we want to acknowledge it or not, age, previous career, financial obligations and goals, family, and other circumstances definitely do play a factor.

But what if they didn’t? What if you could start over?

It’s fun to imagine the possibilities, with a little reason sprinkled in. So lets do just that. Here are the rules:

  • You are 18 again, having just graduated high school at the top of your class and can go anywhere.
  • You can go directly to work or get in to any school, apprenticeship, vocational training you would like. No scholarships – you have to pay 100% of the cost if you choose school or training.
  • You have no kids, no significant other, and you are in great health.
  • You have no debt.
  • You can’t rely on someone else (parents, spouse) for money for the foreseeable future.

You basically get a mulligan, clean slate do-over. Knowing what you now know about your value set, careers, money, status, the pursuit of happiness, and life in general – what career path would you choose, and more importantly, why? And is this scenario still in your future?

Maybe you’d do everything exactly the same, but come on… that’s no fun. No judgments here – so be honest.

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About the Author
I am G.E. Miller, & this is my story. My goal is financial independence ASAP. If you share that goal, join me & 10,000+ others by getting FREE email updates. You can also explore every post I have written, in order.

  • Tim says:

    I would consider doing what I do now (air traffic control) but would have gone to a very inexpensive 2 year technical school to get my certification and would have applied for and ideally been hired at a younger age. The only other thing I would consider would be getting into nursing. Quality career with good wages and benefits. The most important thing to me is feeling like the specialized skills I have are helping people in need of help. I think both of these careers allow a person to do that.

  • Vivian says:

    Do not regret the school I eventually did choose and would gladly have repeated my college experience. I would, however, have changed my entire senior year. Instead of desperately trying to get into the rat race of investment banking or management consulting, I would have listened to the little voice in the back of my mind that told me what I REALLY wanted to do. Would have taken a gap year after graduating to set those plans into motion, and then would have gone for it without hesitation.

    The reality is that I tried a lot of “prestigious” jobs and was unhappy in every single one. Earned some good money, but had no time to spend it and no time to see my loved ones. I’m finally making roads to getting where I really want to be, but 4 years later than if I had just listened to my gut feeling in college.

  • Jason773 says:

    Would have done the same honestly…Top 10 U.S. University, degree in engineering, great job out of college and current plans of getting an MBA. Also had approximately 85k in loans out of undergrad, and I’ll be done paying it after my 4th year out of college.

    I do agree that it’s fun to think about the what ifs, as I’m not in love with my job or the engineering field I’m in (but I’m good at it), but there is too much security and potential to not go this route.

  • Michelle says:

    I honestly think I would do the same exact thing haha. I don’t think I would be where I am unless everything that I did in the past happened as well 🙂

  • Deke says:

    Well if I had to do it all over again with the exact same situation as before, I probably would have accepted the full ride I got to a small state university instead of going to the major engineering school that i did. However, since scholarships are off the table, I probably would still end up going to my alma mater. The difference would be that I wouldn’t start in Biomedical Engineering and go straight into Industrial Engineering (what I ended up switching to sophomore year). My GPA would have held up better, and there were a lot more co-op opportunities in the field giving me a lot more experience on my resume. Despite graduating in a terrible job market, I think those factors would have given me some more options out of school. I probably would have put more effort into getting a consulting job since I would’ve better met the criteria.

    For the record, I did get a good job out of school with a large manufacturing company, but it’s obvious to me that i could be happier doing something else (as apparent by me sitting at my desk writing this comment).

    Oh, and I would invested in Apple.

  • Steve says:

    In real life, I became a military officer after college by attending Officer Candidate School. Though I chose not to extend my commitment past my initial minimum, I felt it was still very useful and opened up doors for me. This route didn’t pay for my college, however. I wouldn’t have wanted to go to the Naval Academy (just doesn’t seem like the normal fun college experience), so I think all I’d have changed was doing the same thing, but Navy ROTC at the same time, to pay for college. I’d probably be in the same place I am now.

    • Deke says:

      In retrospect, I wish that I had at least considered going the Navy/Air Force route (whether it be an academy or just ROTC). I still may have ultimately decided against it, but at the time, it was an option I almost completely ignored.

  • Rachael says:

    I would have worked while getting a two year degree at a local community college. Living at home would have made it easy to save money so I could afford to have a year off to explore the world and figure out who I was and what I actually wanted out of life. I sure as hell wasn’t ready to pick a major/career at 18 and I don’t think many people are! During this year I would have traveled and volunteered. Upon my return I would have gone back to work while applying to transfer my degree to a 4-yr school. My vision stops there. I am not sure If i would have continued on to graduate school like I did, but I would have looked closely at majors that had specific careers associated with them with long term growth/security. No, this plan wouldn’t be nearly as fun as the path I took, but it would have been worth it and likely saved me from the $150k student debt I have now.

  • Anthony says:

    One of my few regrets in college was not going abroad. I did all the paperwork but got cold feet just before I had to put down a deposit. I think a year in Europe would of opened a whole world of possibilities. Although I love my job as a physician, I still daydream about visiting other countries and learning about other cultures. Who knows what route I would of taken? Great article G.E. to stimulate some thought…..

  • Trent says:

    Great question!

    If I could go back, I would have taken a gap year after high school to travel and work abroad. I think very few people can know at the age of 18 what they want to do for a career, and there is no other way than to travel and try different jobs. Afterwards, I would’ve went to an in-state university (rather than the out-of-state that I actually went to) doing my best to stay debt free while finishing school.

    While that is the different path I would’ve taken, I can’t say for sure if my views would be different as they are today. I graduated and worked in corporate finance for 2 years, took a year sabbatical in South America, worked for 8 more months, and am now traveling again. I plan to go into the tourism industry in the near future, possibly creating an online travel agency. So if I could go back from what I’m like now, I would’ve picked a university with a tourism focused program.

    Awesome question! Keep up the great writing, GE!


  • Natalie H says:

    I was super stressed after the rush of an academically challenging HS. So I would have taken a gap year and then gone to a local community college for 2 years to study computer programming. I did two years of computer science in HS and loved it, but for some reason I chose Ecology as my major and I have regretted that decision. I loved studying ecology but it hasn’t made me employable beyond my HS degree. The best position I’ve been able to find in my field would require a move across country for $30k per year. I’m not uprooting my family for that.

    I’m currently a stay at home mom with aspirations to home school my child(ren) so I think my science and math background will help with that. But, if I started my “career” over I would have studied computer programming, because that would lead to a job with a decent wage in something I love doing.

  • Gabe says:

    I would have definitely studied a career related to the internet and web marketing back in 1999 when I started college. Little did I suspect then that now everything to do with the internet and apps would be were it’s at.

  • Dustin says:

    Currently an IT Project Manager at Fortune 150 company in the financial services industry.

    My do-over:

    1. Meet more with HS guidance counselor. Waiting to college to “figure it out” is the worse advice I ever received. Why wait until you’re paying thousands of dollars on school before determining your path? Thats terrible, terrible advice.

    2. Same university. Study more football film and less school work. I’ve used .05% of my schooling in any of the 4 jobs I’ve held with my company. I should have focused more on football, the item I’m passionate about. Plus, I’ve applied so much to life from my collegiate athletics. No substitute for collegiate athletics life lessons.

    3. Medical redshirt my SR year. I would have turned down the offer for my current company and played another semester of football (broken arm sidelined my SR year 2nd game of the season).

    4. Instead of Marketing and MIS degrees, I would have pursued a degree in Exercise Science or Athletic Training.

    5. Post college, would have moved outside the Midwest.

  • Evan says:

    Of course you dont get a do over so this is only useful as it equips you to give advice to other, younger, less experienced individuals you care about. I would have stayed in college longer, taken a bigger, wider variety of courses and enjoyed the absolute freedom you only have at the time and age in the long arc of life. I majored and had a career in computers so it was financially rewarding, provided constant learning and I was n the forefront of technology, which still pays dividends today. However, I would have considered going into “wall street” type of a career to have made a lot of money fast, retired even earlier and thus started giving back sooner. The skills would have been useful for my entire life n making money, managing retirement assets and helping others with their retirement needs. I have discovered that while money can’t by happiness, generosity can. Regardless of career choice, all that matters long term is love, helping others and kindness. And, only God can take you there. 20 Something is a great, useful and meaningful service. I enjoy reading it, regardless I am well over 20 something…

  • Vasudevan says:

    If I am starting all over, the first comes to my mind is to be different than what I am now (does not mean that I am in bad shape now). I would like to travel extensively, create new things in technology, help others more than what I do now.

    One of my dream is to become a secret agent like James Bond and be of help to my country.

    The other one is to join the navy/air force (funny thing is I don’t have the heads for heights / water).

  • Angelo says:

    My career is in I.T. I would say this has been a good career as it allowed me to spend a couple of years working in different cities like Singapore and London.

    If on a reset, knowing what I do now, I’d probably choose to become an orthodontist (dentist+braces). In my experience (myself and my daughter), ONCE ESTABLISHED, an orthodontist does minimal work. They hire dental hygienist to do most of the work, in my daughter’s clinic, we spend 30 minutes or so there with the hygienists, the main ortho just goes in- looks at my daughter’s teeth and say, “All done, see you next week.” (literally in under a minute). Oh and the clinic is only open 3 days a week. You get big bucks with none of the stress of a surgeon where you can kill a patient.

    By the way, your criteria is conflicting, if a person graduates top of the class and can go anywhere, that person will have universities offering scholarship.

  • Amanda M. says:

    I’m a chemical engineer, and have enjoyed the jobs and experiences that I’ve had with this degree. If I did it differently, I would have figured out what an engineer was before my sophomore year. I declared the week before I started as a freshman, but didn’t know what I would be doing in the career, or the opportunities that were out there for females in the field.

    My large high school in the mid-west was not prepared to deal with an engineering mind. I was told that I should be an accountant more than once, because of my calculus ability, a chemist because I loved chemistry, and a teacher because teaching my peers was how I learned best (never mind that kids in general scare/annoy me). There were so many scholarships available my senior year that required you to say what you were becoming, and I had no idea. If I had known, I think I would have gotten at least $5,000 more in scholarships (as it was, I received a presidential scholarship and paid for myself 100% after that).

    I considered going into nuclear engineering, which still intrigues me. I think I would have tried to visit a school with a reactor, if I had known that people actually visit the schools that they are applying to (I was the first in my family to go to college).

    If that didn’t pan out, I think my school (small, accredited program) and my path are pretty much what I would do. I may have taken a few more months to travel, but I took over a year to co-op/intern and the experience that I gained from those breaks from school were just as good as a gap year in my opinion.

  • I recently wrote a similar blog about the most common life regrets people have so I have thought a lot about this. I am also going back to school currently to try and get into a physician’s assistant program. So I can say if I had a do over I would go the pre-med route and go to medical school with the goal of becoming a radiation oncologist before I was 30. They make great money, are in a great field, and have normal hours. I still may end up going that route in the future but for now I am choosing the less lengthy PA path, so I don’t miss my young kids childhoods because I am in med school/residency for the next 8 or 9 years.

  • victor says:

    This is a valuable question that deserves visiting. Recently at a meetup in SF with my college best friend we realized that knowing the results of your decisions in the present is very valuable.

    Imagine being paired up with a mentor who has similar career dreams but ALSO financial goals and then getting those results in the present? every year we here those stories where they poll older retired folks and they ask them their regrets. What do we hear? wish i saved more money, worked less, spent more time with family, took better care of their health.

    I think if kids are trained early on to reach out and plan/learn in this way that we would have less issues with debt,career dissatisfaction, and dead ends.

    just an idea, no app yet. i love this blog it’s helped me sock away $45k in 2.5 years just by reading and acting on it.


  • Samantha says:

    I am currently an environmental engineer. I went to a small, liberal arts school in central PA for my undergraduate degrees in Biochemistry/Molecular Biology and Biology. Degrees were general, and you were required to take a wide variety of courses. An engineering degree did not exist, and I had to go to graduate school to receive my engineering degree. A graduate degree is not necessary for my career, but an engineering degree is.

    Were I able to go back in time, I would go to a larger university with an engineering program or an accelerated Pharmacy program. I actually selected the Biochemistry major with plans to go to Pharmacy school after I graduated, but I was too burnt out to do it. I waited two years and then went back to school for engineering. To this day, I regret my college choice career-wise (I met my husband and made a lot of fantastic friends while there).

  • Rob says:

    I wouldn’t change a thing.

  • Ron Ablang says:

    If I could do it all over again while still single, I think I would enroll myself into a community college to pursue my 2-year degree to become a registered nurse. I should be making at least $69 an hour by now, even more than my engineering bosses make.

  • Logan says:

    Definitely would have gone the medical route. Probably would have been a registered nurse, worked a few years in the ICU and then headed to CRNA school. It is a diamond in the rough $150K+ a year salary for a two year master’s program. Great benefits and security to the position.


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