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Regrets Can Become Opportunities

RegretsI have many regrets. Some are a bigger deal than others. I’m sure everyone can look back over their life and see things a little differently now than they did at the time. That’s the beauty of hindsight. But if you knew how things would turn out before even attempting them, wouldn’t life be pretty boring?

Living is about making mistakes. The expression, “fail fast and fail often” is overused, but it’s catchy. My children’s chess teacher used to say that in order to become a Grand Master, you had to lose 10,000 games. I don’t know how accurate that is, but again, the important point is that making mistakes is how we grow. It’s how we learn. If you are afraid to make mistakes, you won’t get very far.

How many times did Thomas Edison fail at making the lightbulb before actually finding success?

The important part about making mistakes is using what you learn to make progress. If you aren’t making mistakes, you haven’t set the bar high enough.


A Few of My Many Regrets

Failing to get my CPA when I was in school

I graduated with an electrical engineering degree. As an undergraduate, I didn’t take any business classes. And when I went back to earn my MBA, I concentrated in finance. I took a few accounting classes, but not enough to allow me to sit for the CPA exam. At the time, I had no interest in being a CPA. But now that I am 20 years older, I recently wrote about how having a CPA credential would be beneficial both in finding higher level jobs (a CFO position) as well as in generating freelance work.

Leaving my first job too soon

My first job after graduate school was working for a Big Four public accounting firm as a financial consultant. I didn’t realize it at the time, but that job was a highly sought-after opportunity that fell into my lap. During graduate school, I was organizing mock interviews for the students. One of the interviewers was from the firm. When the student didn’t show up, rather than have an open slot, I jumped in and did the interview myself. It went so well, that I was invited back to formally interview for a position. And the rest is history.

Maybe because I landed the job so easily, or maybe because of immaturity, I never really appreciated it. I didn’t care for the structure of having a senior consultant with less experience overseeing my work. I listened to the disgruntled employees always complaining. And  the last straw was when I received a 4 out 5 on my annual review and asked why I didn’t get a perfect score, I was told no one gets a 5 on their first review. I didn’t care for that response and when an outside opportunity came up paying more money, I took it.

In hindsight, that was a short-sighted decision. One of the benefits of working in the Big Four is the network of both former employees as well as clients. But I only worked there for less than 2 years. As such, I really never benefited from either of those. I didn’t stay long enough to make an informed decision.

Leaving a company to take less money

After leaving the Big Four, I went to work for a private equity-backed healthcare company and stayed there for nearly a decade. I ran mergers and acquisitions, financial planning and analysis, and corporate finance. I moved up the corporate ladder. But towards the end of my time there, I got impatient. I wanted to try something different.

I started looking for new opportunities and found a role in my home town. It was in a new industry and paid less, but it was a change and that’s what I was looking for.

But the grass isn’t always greener on the other side. When I started working in a new industry, I realized how much I knew in healthcare and how little I knew in the new industry. I had taken so much for granted and now I barely spoke the same language. The only common element was finance, but it was an industry dominated by hard assets rather than people. The environment quickly reminded me of the Big Four. People had been working there longer than I had been alive and their only motivation was to get laid off and get a severance. I again reported to someone my own age and I was miserable.

Leaving a paying job to start a new company

After only a short period of time with that company, I again started looking for something new. Unfortunately, I had left a good employment market and moved to a small market with very few quality employment opportunities.

Rather than move the family again, I decided to start a new company. And even though I started the business in a new industry, at least it was in a healthcare-related field. But this was the beginning of the great recession. Times were difficult especially when you were trying to get companies to try something new. The business was slow going.

And before it became self-sustaining, I received an offer to return to the corporate world. It came with a regular salary and benefits. I had an entire business unit reporting to me. It was an industry I knew. And even though it required me to travel almost weekly, I couldn’t resist the security it offered.


Don’t Compound Your Regrets by Dwelling on Them

Why do I share these regrets? One reason is so that maybe you can learn from my mistakes and not make the same ones.

Another reason to share is that despite all these regrets, I have been able to put together a pretty good career, make a significant amount of money, and save enough to be well positioned for an early retirement.

The key to success isn’t being perfect. We will all make mistakes. The key to success is learning from your mistakes and not allowing them to derail you.

So how do you keep moving forward in spite of making mistake-after-mistake?

Here are a few of the strategies I use to keep going after a set-back:

  1. Focus on your accomplishments instead of your mistakes. Have you read the book StrengthsFinder? It’s a quick and easy read about emphasizing your strengths rather than looking to improve your weaknesses.
  2. Always reflect on what you learned and how you have grown from any experience. Whether you learn what you don’t like or you learn a new skill, try to come out of every experience stronger than when you started.
  3. Realize that things take time. One of my biggest regrets is being impatient. You need to go into new situations knowing that there will be setbacks. You need to be prepared by having options, multiple income streams, and a support network.
  4. Stay positive, but don’t let your emotions take control of your behavior. I remember when I started my company, if people responded favorably to what I was saying, I felt elated and invincible. I just knew I was on the right path. But when people reacted unfavorably – even in just the smallest way – I felt defeated. I would sometimes even restart and completely change gears.


It would be easy to dwell on my regrets, looking back and thinking about why I did what I did and wish I had acted differently. But that thinking isn’t valuable. It doesn’t matter what you could have done in the past. It really doesn’t matter what you did do in the past. What matters is what you are doing right now. I look back and realize that each misstep I made got me one step closer to what I really wanted to be doing – running my own business. And now that I’m doing that, I’m going to make the best of it.


Readers, tell me about your regrets. How have you overcome your past mistakes? Did you learn anything valuable from them?


Permanent link to this article: http://financialslacker.com/regrets-can-become-opportunities/


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  1. Get FIRE'd asap

    Hi FS, and nice insight to what makes you tick. I think that, after gaining plenty of years experience, and look back at what might have been, it can highlight certain patterns as well. What I see in your career is that you get bored easily and look for change which, if you don;t get in the current role, you seek elsewhere. Would I be right or way off track?

    The reason I see this pattern is that I see the same in my career as well. I have chucked in great jobs with great companies because I’m bored with what I’m doing and get frustrated when I can’t change it. Like you, I know that if I’d stayed at some of these companies, I’d be well ahead today but I don;t look back with regret because I’ve also gone on to do some other fantastic jobs that I wouldn’t have done if I’d remained.

    I still have plenty of regrets regarding other things I wish I’d done differently, and missed opportunities from other parts of my life, but my employment history isn’t one of them.

    So don’t be so hard on yourself. You have probably ended up with way more experience and skill sets that those who stayed behind and toed the company line. Lifers I call them.

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    1. Financial Slacker


      That might be a fair assessment of my career choices, but I also look back on each company and the state they were in when I enjoyed working there and when I did not. In all cases, it wasn’t until the company started struggling and failing to move forward that I started getting frustrated. In fairness, a couple were already in that state when I arrived, I just didn’t realize it until I started working there. But when growth stalls, it often requires making hard choices just to survive – asset sales, layoffs, other major expense cuts. That tends to create a stifling environment.

      We used to say that growth solves all problems. That’s not entirely true as growth brings on new problems, but the idea is that without growth, it becomes difficult to manage a company. Without new clients, it is hard to pay bonuses or even raises. Without growth, you aren’t creating new positions and promoting people. Without growth, you can’t afford to develop new technology. And all of these things are what makes working for a company rewarding.

      When the companies I was working for stopped growing is when I started looking for new opportunities.

      Thanks for commenting and sharing more about your own career decisions.

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  2. Mrs Groovy

    Great share. We can always learn from our mistakes, but as you pointed out, it’s the dwelling on them that can get us into trouble. I know too many people who define themselves by what they view as the bad choices they’ve made. And they never seem to stop talking about their past mistakes as if these things happened yesterday.

    Had you stayed longer at the Big a Four I doubt you would have lasted a decade as you did in your next job. And if you had, the rigidity that prevailed at the Big Four might have snuffed out any creativity or energy you needed to ultimately become your own boss.

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    1. Financial Slacker

      Thanks for the comment, Mrs. Groovy.

      I agree completely. It was only really for this article that I tried to look back with a critical eye on the career decisions I made. In general, I tend to believe that we make choices for a reason.

      When I look back on my career, I see a transition from an external consultant advising companies, to an internal consultant doing M&A, to an internal corporate finance advisor, to a business unit leader, and finally to owning my own business. At each step, I got a little more involved in running the business rather than just being an advisor to the business.

      This progression and what I learned along the way is what is important.

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  3. The Green Swan

    I agree with Martin, life is full of experiences. While your career may have been a winding path it was filled with unique experiences that many would trade for. Good for you for taking some of those risks, working hard, and getting rewarded with many unique jobs / roles.

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    1. Get FIRE'd asap

      Thanks Green Swan 🙂

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    2. Financial Slacker

      Thanks, Green Swan. Each role had it’s own unique situation. And even in the ones that didn’t work out very long, I learned something about myself. Just keep moving forward is really what you need to do.

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  4. Dividendsdownunder

    Hey FS, that’s a lot of life experience lessons in one post, I appreciate you writing about it.

    It’s amazing how much a qualification helps (and sometimes how little). I’ve recently joined up to do a qualification so hopefully that will really help in my life for our lives.

    No-one is perfect, the world doesn’t go without hitches, that’s life I guess 🙂


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    1. Financial Slacker

      Thanks, Tristan.

      When I talk to people with their CPAs who work in finance, they almost always tell me that having a CPA doesn’t matter. But they wish they had their CFA. I usually feel the opposite. I have my CFA, but many people don’t even know what it means. Whereas, everyone I come across knows what a CPA is and what it allows you to do. But with that said, I’m not sure I would have been very happy working in accounting all these years. I much prefer the route that I took.

      It’s hard to predict what will happen down the road. If I was living in New York, my CFA would carry much more weight.

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  5. Stefan - The Millennial Budget

    So glad I got to read this post as you know that I am going into Big 4. I am glad that I have started my CPA, hope I finish it before I begin working. I heard that they are brutal with performance reviews so I hope to learn from your experience and be patient as it will work out in the long run. Thanks for sharing the experience as I can directly relate to this.

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    1. Financial Slacker

      I’m pleased to provide my insight, Stefan.

      The Big 4 is really a great place to begin your career. For some, it’s a starting point, and for others, it’s their entire career. Either way, you will find yourself immersed and learning from clients, team members, and from the internal workings of the firm.

      After all these years, I am still in regular contact with my first Big 4 Manager. And even though I didn’t stay too long, I can still call up any one of the people from my starting class for any reason.

      Enjoy the experience. No matter what happens, I think you will look back on it fondly.

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  6. Amanda

    Thanks for sharing! It’s great to read about the lessons you learned along the way. I agree, you have to have patience and focus on the positives.

    I have too many “fails” to list, but I have a deep appreciation for all of them. I had a “failed” business – so many important lessons learned from this one. My daughter recently asked me if I felt like I wasted two years on that business. I told her no I didn’t feel like the business was a waste of my time at all – I met a ton of awesome people, was able to share my knowledge to help others, and learned a great deal about business and life along the way, but it was just time to move on.

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    1. Financial Slacker

      Thanks, Amanda.

      That’s exactly how I feel about my last business. It’s hard to explain to people who haven’t been through it. Sure, I would have loved for it to have taken off like a rocket. But instead, it lead me to another corporate role leading a business unit. That role gave me the opportunity to work at a smaller company (still $30 million in revenue, but small compared to public companies and Big 4). It also gave me the chance to manage large groups of people. Those are experiences I can carry forward into my current and future ventures.

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  7. FinanceSuperhero

    This is a tough topic to write about (and think about, for that matter). My biggest regret is leaving my first job too soon, as well. However, it has helped me redefine what I really want to do for the rest of my life, so in that sense, my error may yet work out in my favor.

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    1. Financial Slacker

      Thanks for the comment, Finance Super Hero.

      Leaving your first job too soon seems to be a common occurrence, especially among the Type A’s. I also saw it in the people I managed. Many are so eager to move forward, and feel like they know what we’re doing, that they don’t take the time to listen to others that have been around for a while. That would be my advice for people just entering the workforce, don’t discount the people with experience. They may actually know something valuable after all.

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  8. zeejaythorne

    It is so important to learn from your mistakes and to also realize that you made them at all. My biggest mistake was not starting to temp sooner. I was unemployed or underemployed for 1.5 years at the end of grad school. I could have started temping and earning appropriate money during that time. This would have helped to keep me in my neighborhood, and would have given me more reason to get out of a bad relationship. However, I don’t know if getting so low was pivotal in starting my own business.

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    1. Financial Slacker

      I agree, ZJ.

      I still find myself looking back over the past year and wishing I had done something differently. When you look forward, the future seems limitless. But when you look back, you realize how fast time flies. Don’t wait. Get going on whatever it is right now.

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  9. Finance Solver

    Thank you for sharing. I like the attitude in which that you reflect back on your regrets to figure out what you would do differently next time around and focusing on the good that came out of your choices that you’ve made.

    My biggest regret is doing too much without reviewing my goals. In college, I double majored, triple minored, and had multiple jobs throughout, and while it was good in that it kept me busy, it wasn’t good that it wasn’t focused. Had I had time to review my goals and where I wanted to go, I would have realized that sooner but I realized that lesson towards the end of my college career. Will certainly be doing things differently once I start working.

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    1. Financial Slacker

      Thanks for stopping by, Finance Solver.

      Double majored, tripled minored, and had multiple jobs. Wow! I thought I was busy getting an electrical engineering degree with a biomedical specialization. I can’t imagine how difficult that was for you.

      I think you should feel great about having accomplished something that very few could have achieved. My guess is you have learned to be very disciplined and driven to succeed with that course of study. Those skills will take you far in the working world.


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