My failure resume: the many mistakes made on the path to success

FAILURE on Chalkboard

My Failure Resume

If you think that successful people are void of any failures in life, you are just plain wrong.

And what is success anyway? Is it the amount of money in your bank account? Or is it being a valued member of your community? Is it earning accolades, or simply being a good person?

Everyone has their own definition of success, and mine has changed quite a lot in the last few years.

Yet, even if you do consider me to be a success, (because I have a solid net worth, was a CEO of a $15M company, managed to FIRE accidentally, etc.) my success came with many failures along the way.

My failure resume: the many failures on the way to success

You can’t succeed at anything without failing along the way.

When I was in the process of leaving my CEO job nearly a year ago, I decided to create a Failure Resume from my time with the company (nearly 10 years).

The goal was to take all of the learnings from my failures, so that I could both move forward by leaving the mistakes in the past, and learn from my mistakes at the same time.

 A willingness to chronicle your failures helps to create the kind of resilience that allows you to get beyond them.

Harvard Business Review – Write a Failure Résumé to Learn What Makes You Succeed

Many of these failures were very personal, others were systematic. But all failures can be learned from.

And I hope that by reviewing my failures, I can help others move past their failures as well. In the words of Melanie Stefan in her viral post A CV of failures “it might inspire a colleague to shake off a rejection and start again.”

Here are my failures both personal and professional. At least the ones I can remember…

My professional failures:

No partnership agreement in place.

My career was going great. I started off my career by assisting a mid-size startup in spinning up a new division. The division was essentially myself, the CEO, and a 3rd party marketing firm.

I also had a side hustle, that I was passionate about and working nights/weekends on. The goal was to use this side hustle to get a full time job in an industry that I was passionate about.

Out of nowhere we got an offer to buy the business that included full-time jobs with another mid-sized startup. The offer wasn’t for much money, but it gave my business partners and I the opportunity to work in the industry we desired full-time.

The problem: one of my business partners did not want to sell the business. Working in the industry wasn’t his goal.

But we didn’t have any partnership agreement in place. We didn’t have any proper founder vesting in place. All we had was a handshake agreement. It was a disaster.

Ultimately we figured it out. This partner agreed to sell, and he opted out of taking the job.

The lesson learned was to always have a partnership agreement in place. And ensure that there is proper vesting schedule put in place, so that if a business partner is not contributing as much, there is a vehicle built in to assist with that partner’s departure.

My first business…went out of business.

Yep that is right. It just straight up failed.

After we sold our small business to work in the industry full-time, we were too unfocused. We didn’t foresee the need to scale revenue as aggressively as we thought.

My business partners and I flailed about with our heads in the sand ignoring the reality of the situation. Our parent company was failing, and we were going to be the first ones to go.

Instead of focusing on having a cohesive plan, we were too apprehensive.

The lesson learned: I should have taken charge of the business altogether. We had let our buyer come in and bring in a boss to manage us. He was completely ineffective.

I felt stuck between a rock and a hard place. I tried to lead by example, but in retrospect, I should have spoken up and taken charge of the team even without the official title.

Not prioritizing revenue and sales

I ::shocker:: have made this mistake twice with two different business’.

Thankfully only ONE of the business ultimately failed. The other became successful despite it.

I didn’t prioritize revenue. I didn’t focus our team around selling and building a customer base.

My general feeling was that if we built a great product, bootstrapped, and attracted enough users, then the sales will come. Wrong!

If you want to sell any business, or attract investors to your business, investors and buyers will not only want to see product-side growth, but they will actually want to see some revenue growth as well.

After selling my first business, we even had a sales team member. But we just let him do his own thing. In the end, we should have all been on the phone making sales calls and ensuring the stability of the business.

That business ultimately failed, due to lack of positive cash flow.

The lesson learned should have been to prioritize sales and revenue along with scaling the user base.

But I made this mistake twice.

I did it a second time in my latest business. We made half hearted efforts to bring in sales folks, but never actually fully committed.

In hindsight, we were very lucky. We were able to find the right buyer for our business at the right time. But had we had our own full blown sales team, we might have not even needed to sell the company. We likely could have scaled much faster. We would have been able to control more of our own destiny.

Don’t forsake your revenue for your product.

You must have more balance than my business’ did.

Using Voodoo hiring methods

This is another failure that I made multiple times.

Over the years, I have hired numerous employees. Many worked out, but many…did not.

Why did this happen? Why did I continue to hire folks who just didn’t seem to be the right fit?

It turned out that I was using Voodoo Hiring methods – that is hiring using anything from a gut feeling, to overselling your company, to not deeply ensuring the hire is a good cultural fit, to hiring someone because on paper they knew their stuff.

Not once did I actually check any references myself.

I always let HR handle it.

The bottom line was that I had no system for hiring people. And I love systems!

The results were bad cultural fits, cancerous employees, misjudgements of character, and resulted in chaos and ultimately needing to fire one too many folks.

The lesson learned: I picked up a copy of Who: The A Method for Hiring, by Geoff Smart and Randy Street. I put work into adopting their system and implementing it across our entire organization.

By the time, I left my job, every hiring manager had not only read the book, but been trained and utilized our version of The A Method for Hiring. The results were that we made stronger hires and it is something I will continue to use in my hiring process.

Being too complacent – Not pushing myself to be a better leader

We sold our business while it was still growing. As part of our earnout agreement, we continued to be incentivized to stay with the company and grow it.

Yet, I took my pedal off the gas.

I stopped pushing myself as much to learn. I rested on my laurels.

I felt confident that I knew what I was doing, yet instead of reading about leadership or how to scale a company from 15 to 100 to 1000 employees, I was reading Game of Thrones and other novels to take my mind off the stress.

Now, don’t get me wrong. There are a time and place for novels and I needed that peace in my mind at times.

But the lesson learned was that I should always be continuing to better myself. Once I realized that I wasn’t growing, it wasn’t that I was just stagnant – I was floundering.

I decided to pick up books like The Effective Executive: The Definitive Guide to Getting the Right Things Done by Peter F. Drucker and Good to Great Why Some Companies Make the Leap and Others Don’t, by Jim Collins.

I started to put myself on the path back towards growth. And the results were that I was able to turn myself into the leader that I wanted to be.

But no matter whether you are self-employed or running a 1,000 person organization. You should always be pushing yourself to learn. To earn your job, each and every year. Even if you are the CEO.

A splendid temper tantrum

I could go on for days about my professional failures. I had many of them. There was a time when I was so frustrated with a senior employee (and a great employee) over a very minor spat, that I told him he should consider resigning immediately.

I then threw a temper tantrum and stormed out of the office and didn’t come back for a few hours.

Ultimately, I came to my senses and apologized. But you can bet that went on My Failure Resume when I was leaving the company.


I’ll stop there with my professional failures, or this post might go on forever. I’d like to cover some personal ones as well.

My personal failures

Leaving too many relationships behind

Because I was so focused on myself and my own success for years, I wasn’t putting in the work to be the best sibling, son, and friend that I could be.

In fact, I wasn’t even putting in the work to be the best husband that I could be.

I was so self-absorbed and focused. I was obsessed with my career and my success.

There were times that I was able to course correct, but ultimately I spent my late 20s and early 30s with my head down working.

And though I always have carved out good work-life balance working 40 hours a week or less, I still was thinking, breathing and eating work far too much.

So the result is that I failed to build solid relationships with my siblings, my parents, and my friends. My relationship with my wife is good. She has been my rock, but I know that I could have done better during that time.

Ultimately, I just failed at being the best I could in these relationships. I thought I could coast – and you can’t coast with relationships.

You have to put in the work and the effort.

Selling our first property vs. renting it out

My wife will disagree with me, but I do regret selling our first property.

It was a patio home that now rents for $2,000 a month. Our mortgage at the time was $1,200 a month.

The home was 10 years old and starting to need some major repairs, such as roof, re-paint, etc – but it was still relatively low cost, because it was so new.

We sold the home quickly for a small gain, but after closing costs and realtor fees, we didn’t end up making any money.

Yet, if we had held onto the home, we could have created positive cash flow for us, and let the renters continue to build up our equity in the house.

That same property is now worth $150K more than we sold it for (5 years ago).

If I was to buy a rental property today, I would probably want to buy a comparable home, but the cash on cash returns and cap rate are much worse today for this same property due to the surge in cost.

So from a financial perspective, this was a failure to think ahead.

The lesson learned for me, is to run the financials on your own property before you go to sell it. Perhaps it doesn’t make sense to keep it, but you should investigate at a bare minimum before making any decisions.

Voodoo hiring our financial advisor & not spending more time learning about investments

Similar to my failed hiring methods as an entrepreneur, I failed to thoroughly vet out our financial advisor. I asked for a family recommendation, and had a couple of calls with the guy.

Then my wife and I had dinner with him, and the rest was history. High fees and all.

Not once did I even consider either talking to another financial advisor, OR managing my own investments. But as JL Collins puts it:

If you are a novice investor you have two choices:

You can learn to pick an advisor.

You can learn to pick your investments

JL Collins

I did neither and it came back to haunt me.

The lesson learned for me was: You should learn to manage your own investments, because too much can go wrong hiring an advisor.

I fired this advisor in December, and haven’t looked back.

Managing my own investments is easier than I ever could have expected. I invest in Low-Cost Index Funds, have created a personal financial plan, and use Personal Capital to review my budget and net worth (affiliate).

Taking ownership of my finances, helped me to realize that I could Accidentally Retire. All it took was a little effort.

Failure is part of life

As you can see. I have had plenty of failures on my path to FIRE.

It is a part of life. But by embracing your failures, looking them in the eye, and ensuring that you learn from your mistakes, you will do better next time.

You can’t NOT fail. Especially if you’re going for greatness.

J. Money – My Resume of Failures

We all fail. In my above failures, I even repeated the same failures multiple times, before learning from them.

Failure is life. And the bigger your goals, the greater your failures are likely to be along the way to success.

Now go out there and fail. You got this.

Other notable Failure Resumes:

Do you have a failure resume? Let me know and I’ll add it here:

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7 comments

  1. AR – really enjoyed this, and reminded me of some of the mistakes I’ve made over the years. I’ve got a mental note of some of the work instances where I wish I could have taken a mulligan. Most of my issues would have been resolved by better communication on my part, or being willing to ‘unofficially’ take over certain tasks where I could see they were failing but cared more about not offending someone than about fixing the problem. Recently posted about some of my mistakes in discovering FI, but I love the work focussed write up.

  2. AR, this post was so informative! It was great to see what goes on behind the scenes with management at companies. No one is perfect and you’ve certainly shown how failing quickly will also get you to success quickly! I really appreciate your transparency in this article.

    1. I can certainly give some more behind the scenes going forward…In my experience, all management cared greatly about the company, its performance, and people. But like anything in life you make mistakes, you don’t give a promotion that is deserved, you promote someone who doesn’t deserve it, etc.

      You do the best you can with the information and resources you have. And that is life in general I am finding. Everyone is just doing the best they can do, with the hand they are dealt and the information they have at that time.

  3. Thank you for sharing, AR. I feel that failures are a part of life and I think the biggest regrets we’ll have is on the failed relationships aspect. I wish there were no tradeoffs between choosing ambition over relationships.

    I definitely wish I had more close friends but that would mean a lot of investment and time into them and to be honest, financial independence is just on a higher priority now. Once I become financially independent, it’ll be difficult to make genuine, new friends so there’s that aspect as well.

    Life is hard!

    1. There are trade offs, but I think this was also on me. I know I could have done better. As I get older I am finding that the things I create a system for, I tend to do well with. If I don’t create a system, then I flail about. Friendships are no different. So as of late, I have tried to create a system to remember to text a different friend I want to hear from every now and again. I also try to have either a Zoom call or going forward lunch or happy hour with a friend once a week.

  4. I feel weird about this, because my career was always much more successful than I expected. There were no great failures, I was very good at chemical engineering and rose from summer intern to running a billion dollar operation and I can’t think of any big mistakes. I misjudged a few people and some of our technical designs weren’t awesome but we didn’t have any disasters either. I had some situations where I nearly made super bad decisions but our system of checks and balances always stopped me safely. Even in my personal life, I failed to qualify for the Boston marathon, but it wasn’t a lack of training, I was just too slow. I lost a lot of tennis matches, but again I’m not a gifted athlete, I’ve probably over achieved given my DNA. Maybe I just gloss over failures, but I don’t have hardly anything I’d change if I had a do over, personal or career related.

    1. I think that’s great that you didn’t have as many, if any!

      Clearly you could have had a big blunder, but there was a system in place to stop you. As an entrepreneur, I was more prone to making mistakes due to the nature of growing a business without prior experience. It’s always two steps forward one step back, even on good days.

      But if you are working in a stable career in a stable company, there is nothing wrong with that. You succeed with less drama and failures to boot.

      I think the important part is to not let failure bother you. You can move past it (or gloss over), you can learn from it (if there are learnings). Just don’t let it bog you down.

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