My 5 Biggest Financial Regrets

We all do or don’t do things during our lifetime that we end up regretting. These regrets can be as simple as having one scoop of ice cream too many, wearing heels instead of flats, or having a messy house when surprise guests show up.

Other times regrets can be bigger and have a bigger impact on our lives. They can have an impact on our finances. Some of my biggest regrets are finance-related because they had a lasting impact on my finances. The good thing about having these regrets is I’ve learned from them and can share those learnings with you.

money missed out on by making big financial mistakes.
(This information is not meant to be financial advice and is just for educational purposes. This post may include affiliate links. Should you click an affiliate link and make a purchase I may receive a small commission at no extra cost to you.)

Financial regret 1: Staying at the same job for 5 years

I got my first full-time job about nine months after graduating college. I was so excited about that job. A few years in I wasn’t happy anymore. I didn’t feel like my career was being nurtured or that I was getting the kind of experience that would help me grow my career.

As a result, I seriously considered leaving to the point that I was interviewing at other companies and had accepted other offers, but something or someone would convince me to stay.

I soon came to regret staying because after being at that job for five years I was laid off. That company was known for having layoffs every 1 ½ - 2 years even to this day. So I wasn’t too surprised it had happened, but it was still a shock.

Since then I’ve come to realize that staying at that job and the layoff both had a huge negative impact on my earning potential. If I had left that job after a couple of years I could have
  • Increased my salary sooner and earned more over time. Some research has shown that staying at the same employer for more than 2-3 years can cost you up to 50% in lifetime earnings!
  • Not lost my job and been out of work for a few months which ate into my emergency savings and negatively impacted my retirement savings.
  • Gained greater work experiences that would have enriched my resume putting my career on a better growth track. 
If you've been in the same position at the same company for several years take some time to assess whether you are making the market rate for that position. From that assessment determine if it's time to leave or ask for a raise. If you do ask for a raise you'll want to do it right. Career coach Ken Coleman gives great advice for asking for a raise in this article

Financial regret 2: Taking a job for less pay

This happened after the layoff I mentioned in the previous regret. I had been unemployed for a few months and was getting worried I wouldn’t get another job. So I ended up taking one that paid $10,000 a year less than what I had been previously making.

Now sometimes taking a job for less pay isn't a bad thing if it's a stepping stone or pathway to get you to a better position. Going this route I'd only be willing to take less pay for no more than a year or two.

In my situation, this wasn't a way to grow my career or get a better role. I feel it put me behind in my lifetime earnings by putting me in a salary bracket lower than I should have been in. I’ve been playing catch up ever since which could result in me earning less over my entire lifetime.

Financial regret 3: Not increasing my retirement account contributions over time

When I first started working I made sure to contribute to my retirement accounts religiously. I increased those contributions regularly and whenever I got a raise. That is until I was laid off.

When I was laid off I stopped contributing to one of my retirement accounts and drastically reduced the contributions to another. When I started working again I didn’t resume those contributions for several months. The reason was that I felt I needed to replenish my emergency savings in case I was laid off again. Because of this I’ve gotten behind in my retirement savings and will be playing catchup for a while.

When I did resume my retirement contributions they were minimal. It was several months after I was employed again that I increased my retirement contributions to a point where they were substantial and closer to where they would have been if I hadn't stopped making contributions.

Unless your income drastically decreases or goes away keep contributing to your retirement accounts. It seems that the most common advice out there is to invest at least 10-15% of your income and to keep investing even when the market dips.

Financial mistakes to avoid | A Relaxed Gal 

Financial regret 4: Missing a few credit card payments

I’m a person who pays her credit card off every month so I don’t carry over a balance. This has been great for my credit history and put me in good standing with my credit card companies.

So it may come as a surprise that I’ve missed a credit card payment or two. These payments weren’t missed because I didn’t have the money. It was pure stupidity. I just forgot to make the payments.

While this only happened a handful of times, I regret the missed payments because I wasted money. I had to pay late payment fees on the balances and some crazy interest. Additionally, a few of the late payments were added to my credit history and impacted my credit score.

The best way to avoid this is to either set up automatic payments or get rid of your credit card and only use cash or a debit card.

Financial regret 5: Not working with a financial advisor sooner

Within the last year, I started working with a financial advisor. She helped me map out my short and long-term financial goals took a look at my overall financial picture and gave me recommendations on how to reach those goals. This has been helpful as I work to get my retirement savings back on track.

I wish I had worked with a financial advisor sooner. Those who work with a financial advisor are able to replace up to 80% of their income in retirement versus those who don't. That’s a big difference.

If you aren't working with a financial advisor you can find one by asking friends and family who they use. Or you can search The National Association of Personal Financial Advisors site

Do you have any financial regrets?


  1. Replies
    1. Sorry to hear that. Hopefully another opportunity will pop up.

  2. Regret 4 makes me mad when I do it. I hate paying more money because I forgot to schedule the payment of put it in the mail early enough. Great post!

    1. Thanks! I now have reminders texted or emailed to me from the credit card company about a payment being due. That then prompts me to set up a reminder on my calendar app. I haven't missed one since I started doing that.

  3. I feel like I'm in #2 and worry that I may not be able to move out of being in jobs of the wrong salary bracket. Any tips on how to get out?

    Danielle | <3

    1. I'm sorry to hear that Danielle. I ended up leaving that job after about 6 months. Once I worked there for a few weeks I realized that wasn't the place for me and needed to increase my income. So I started looking for a new job and found one quicker than I anticipated. While it didn't get me back to my previous income, it got me $5k closer.


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