Everybody stumbles at some point. The question is:
What do you do next?
The best career mistakes are those you learn from and that put you on a better path
Agonizing about the academic degree you got? The decision to accept a job you had doubts about?
Your regrettable candor in that meeting? The avoidance of a small problem that then nearly
torpedoed your whole reputation?
You’re not alone. We all stumble at some point in our careers. Sometimes, we bounce back quickly.
Sometimes, it takes years. And sometimes, we never quite recover.
The best mistakes, though, are the ones we learn from, and that actually boost our career and put
us on a better path.
In that spirit, we asked Wall Street Journal readers to tell us about the biggest mistake they made
in their career—and what they learned from it.
Don’t forget the soft skills
For me, being in the finance and accounting field, the biggest mistake was overfocusing on gaining
certifications and credentials as a way to move up in my
I learned this the hard way once I became a middle manager and got stuck. I was torn between doing
the right thing for my employees, earning the respect of my peers and pleasing my superiors. I did
not know how to navigate office politics, HR issues and so many other things.
My superiors had fewer credentials than I had, but were so much better at everything else—such as
breaking down complex accounting terms for nonfinance people to help make better business
decisions. Their insights, acumen and soft skills made all the difference.
Now, I work on those skills with as much passion as I used to pursue letters after my name. My
advice is to be balanced: Focus on building subject expertise while learning how to negotiate to
better advocate for yourself, your team and your projects. Build a personal brand inside and
outside of your company through leadership and public speaking.
Yes, having credentials can open doors, but they don’t guarantee you making it up
• Wassia Kamon, John’s Creek, Ga.
It isn’t all about the money
An investment advisory firm offered me a job as a portfolio assistant with a definite path toward
becoming an investment counselor. When I told my current job that I would be leaving, they quickly
countered by offering to double my salary. I foolishly accepted the salary increase. That job never
provided an opportunity to advance.
I learned a big lesson: Never take the counteroffer.
• Kathleen Franks, New Rochelle, N.Y.
Call attention to yourself
My parents came from nothing, and everything they had they attributed to their very hard work. They
were quiet people, and would never have dreamed of calling attention to themselves. I applied the
same strategy to my career, always striving for excellence, but never touting my work in the belief
that my managers and supervisors would see my value and reward me accordingly.
When I was coming up through the ranks, “face time” was a thing. Who was the first one to work
every morning and last to leave? Who was spending time in the boss’s office, who was a loud voice
in meetings? This made no sense to me. Why be in the office if there wasn’t work to be done? Why
bother the boss with idle chatter? And, most of all, why would I ever speak up in a setting where I
didn’t have valuable input to contribute?
SHARE YOUR THOUGHTS
What were your biggest career mistakes? Join the conversation below.
It took a long time for me to realize that the people I considered blowhards or glad- handers were
moving ahead, getting promoted and following their mentors or sponsors from firm to firm, while I
was still head down, doing the work.
The light finally went on when I was approached about a new role by a former colleague, and
realized that I had to get out of my own way, break old habits and promote the heck out of myself
to make this happen. My new manager—himself a master of self-promotion—also boosted his team the
same way. I felt encouraged and therefore secure enough to be able to talk about the extent of my
contribution as part of that extremely smart and accomplished group of professionals, and that
fueled me to reach new levels of productivity. I now actively seek out competitive,
collaborative work environments like this and wouldn’t consider working anywhere
It’s a much better way to go through life, but I believe it requires both bravery to put yourself
forward and support from management. I think there’s a way to promote oneself and advocate on one’s
own behalf without acting like a complete egotist, but it’s a delicate balance. I spend a lot of
time building up younger team members, focusing equally on those who lack self-confidence and those
who have perhaps a bit too much of it. Nothing makes me happier than seeing one of them doing great
work, acting justifiably proud and receiving the acknowledgment she deserves.
• Mark Roth, Toronto
Have patience and empathy
My company was experiencing some operational problems that led to tighter cost controls and hurt
employee morale. I became impatient with management’s reaction. They were so focused on the
problems that they seemed to stop taking care of employees. I thought this would affect my career
trajectory and personal development, so I left, sooner than I should have, resulting in a couple of
additional moves between firms, and creating an unstable-looking résumé.
In hindsight, I should have been more patient with the company’s situation and ridden out the storm
with them, rather than reacting hastily. My advice would be: Don’t react to management decisions
too emotionally. Instead, try to put yourself in their shoes. What could I have done differently as
a leader? Could I have helped with ideas to implement better procedures or provided moral support
to those around me?
Additionally, don’t jump on the bandwagon of complaints. Don’t jump off the cliff because everyone
is doing it. Nobody is perfect and, often, we cause our own problems. Thus, constant
self-examination is of paramount importance. I believe this kind of thoughtful consideration would
have placed me in a far better position today, both as a professional and human being.
• Min Cho, Brea, Calif.
The danger of being comfortable
My decision to leave Navy recruiting duty and return to a corporate job was the biggest career
mistake I’ve ever made. I left the Navy to go back to an old job that I thought was comfortable for
me. But it turns out that I had outgrown the old position and it was no longer challenging.
Still, I stayed four more years back in that old role without any advancement opportunities. I
finally left for good, regretting the time I lost and the anguish I put myself through trying to
stay somewhere I wasn’t happy just because the company had regular hours, great benefits and was
Ultimately, I got back into recruiting with a transportation company. I finally had flexibility,
social interaction and challenging work.
• Saquonna Duncan, Sandy Springs, Ga.
It isn’t personal
In the mid-’90s, I was a minority partner in a very small technology company in a
specialized field. In 2003, we were purchased by a firm based in Europe.
My contract to stay on was for three years, with an optional fourth. Initially things went
smoothly, but during the fourth year, “Europe” became much more involved in running our business,
which I resented. Although there were talks about extending my contract for another year, those
talks broke down and rather than wait it out, I simply quit at the end of 2007, thinking I could
wait a few months and enjoy life before beginning a second career in a new field, as long planned.
Remember 2008? Recession, the stock market tanked, unemployment spiked. By the time I realized that
my retirement savings were over 90% equities it was too late.
My hopes of a second career didn’t pan out until 2010 due to economic conditions and my retirement
date got extended by several years.
Here’s what I learned: Just like “The Godfather” movie, it isn’t personal, it’s business. Anger and
bad emotion toward your boss is harmful—to you. If I had just shut up and stayed working into 2008
under the terms of my old contract, then they would have had to either send me a contract or let me
go. Involuntary termination would have drastically improved my family’s life in 2008-09. Instead, I
made it easy for
“Europe” by quitting.
• Frank Arciuolo, Stratford, Conn.
Fear is a bad excuse
My biggest mistake was being afraid to move away from home. I grew up near Philadelphia and went to
school nearby, getting a masters in computer science from Villanova in 1981. I applied to IBM and
got an offer at the Endicott, N.Y., facility.
Even though I held IBM in the highest esteem, I turned it down. Frankly, I was
scared to move away from Philly after 30 years and start over. I reapplied for jobs at IBM over the
next decade, but they never answered another one of my letters.
Then in 1993 I saw an opening for a development role at IBM’s Rochester, Minn., lab. I applied, got
an interview, and an offer. They gave me six weeks to decide, and I spent them changing my mind at
least 30 times a day. If I went to sleep deciding to accept the offer, I woke up deciding to reject
it, and vice versa.
Finally, I realized that if I ever wanted to break out of the career rut I was in, I would have to
take a chance. So I accepted, loaded the cats into the car and started the long drive to Minnesota.
By the time I got to Harrisburg I had again decided it was a mistake, but I convinced myself to
just drive to the next exit, and then I would turn around and go back. I kept doing that for the
next 200 miles until the spell finally broke near Pittsburgh.
Three days later I was in Rochester. It turned out to be my dream job, and ended after 22 months,
but I was never afraid to move for work again.
Taking this new job more than a thousand miles away from everything I ever knew and everyone I grew
up with was unbelievably stressful, but also revitalizing. My career took off from that point.
Having IBM on my résumé opened a lot of doors. I decided to move to North Carolina for more job
opportunities. If not for that move, I wouldn’t have boosted my salary again, and wouldn’t have met
my wife. Sometimes, just sometimes, fortune favors those who are willing to take the risks.
• Bradd Schiffman, Winston-Salem, N.C.
Ask for what you’re worth
In retrospect, I have to admit that I was not confident in negotiating my salary when I first
started my corporate journey. It was a mix of being grateful that I had a job during a recession,
being a woman in a male-dominated company, and inaccessibility to the right mentor.
Now, as the owner of a tech startup, the tables have turned. It is such an incredible experience to
see how women understand their worth and are now initiating those tough conversations with their
bosses with confidence.
Instead of just asking for a raise, I encourage all of my mentees to build a portfolio of every
successful project to have ready for those conversations to use as ammunition. Your boss will have
tangible, irresistible evidence of your value.
• Misha Shah, Tulsa, Okla.
Don’t be scared of asking for help
I love this question. My greatest career mistake was refusing to ask for help when I was burned out
in an industry that expected total dedication. Instead, I suddenly left a job I loved and had
worked hard to get. And when a bigger, better job in the same line of work came calling, I couldn’t
pursue it because I had no good explanation for why I walked away.
Frankly, it wasn’t a time when asking for help was even talked about. As a young woman in a
competitive newsroom, you didn’t raise your hand and say, “Hey, I’m covering a lot of trauma. I’m
struggling. I need a break.” No one ever said to me, “If you take a step aside, you will never get
another great assignment.” But that’s absolutely what I believed.
So I quit abruptly and had nothing I could say to a recruiter who sought me out for a great
journalism job. I couldn’t tell an editor at a national news outlet in 2001, ”Well, I needed a
break and I wanted to stop drinking so much to cope with work, and I didn’t know how to ask for
help.” We’ll never know how it might have landed, but needless to say I opted for a vague answer.
Then followed a period of career instability: freelance writing, magazine editing and a bookstore
coffee shop. Today you would call that period a mental health break!
But it felt more like I had run totally off course. However, the search that followed eventually
led me to a very unexpected and rewarding career as a content officer for high-tech firms. All
these years later, I’m gainfully and happily employed in a more stable industry filled with smart,
creative people, while a lot of my former peers have been scrambling to find new careers or second
What would I do differently? I guess I would tell my younger self: Set aside your pride. Raise your
hand and tell someone at the top what is going on, even if it’s difficult. There might be a path
forward in your current organization that you haven’t even envisioned yet. Whatever happens, don’t
leave on a bad day—plan your goodbyes for a good day.
• Ellen O’Brien, Boston
Pride or arrogance?
In my early career days, if I didn’t want to do a task, I made it known that it was “beneath my
skill level” or “didn’t dovetail into my goals,” believing that stance would show my bosses that I
was meant for bigger and better things.
Invariably, when I was still stuck doing those “menial” tasks, I let it make me miserable and I
ended up hating whatever job I was in. I would leave after one year, thinking I had to find
something better. I developed the reputation of a job-jumper. It took until my mid-30s to break
that pattern and rehabilitate my reputation, and meanwhile I lost out on a lot of great
opportunities to further my career.
Who knew being self-centered would lead to professional difficulties?
While I try not to regret this too much, I have since made up for lost time, and am currently
working in my dream job for an amazing company, with a great management team. Still, I wish I could
have accomplished my current level of success while my Mom was still alive to see it. She
single-handedly raised my brother and me after our father walked out on our family; she worked too
hard for her children not to reach greatness. I regret not understanding all this about myself and
my Mom sooner, so that she could see her hopes for me come true.
As a manager, I now consider who has the most to gain from a less-than-glamorous task before
passing it along, and I never ask someone to do something I am not willing to do myself, time
permitting. Being a team player is what got me promoted to leadership positions; staying a team
player is what keeps me there.
• Kimberly Manchester, East Providence, R.I.
Beware of dreams
My biggest mistake was having unrealistic expectations when I graduated from
college in 1990 during a recession. People tell college graduates to “chase their
dreams,” so I chose to hold out for my dream job instead of accepting a lower-level job where I
could move up. I finally recognized reality nine months after I graduated, but by then the economy
was deeper in recession, and it took several years before my career was where I wanted it to be.
• Joe Wolf, Minneapolis
I was recruited to be an executive at a firm in my industry. They hired me because I had solid P &
L experience that they were lacking. I was a bit concerned about the culture being open to changing
some things, but I was definitely seduced with the opportunity. (They also increased my salary by
50%.) It turns out the company was totally resistant to changing, even in small ways. I thought I was
prepared for it, but I wasn’t prepared for senior leadership to be the main source of resistance.
The adage “be careful what you wish for, because you may get it” was too true here—they said they
wanted change, but they couldn’t or wouldn’t accept even minor changes. After a few years, I had to
The main learnings were twofold for me: 1) check my true motivation for a new role (the
compensation and the allure of a big role was seductive over some red flags); and 2) be more
diligent about understanding the real culture of the organization (culture eats strategy every
• Mitchell Nash, Longmont, Colo.
Had I not gone to law school…
My partner and I started a small computer-services company in the 1980s that was bought out by one
of the industry leaders. After mulling what to do with my life at age 39, I decided to go after my
college dream of becoming a lawyer.
The week I was supposed to report to law school, I was at a local computer store. These were the
very early days of retail computer stores, and it wasn’t unusual for novice consumers to be
conversing with computer professionals like me who were also fellow shoppers.
As I walked past the software section, there was a couple confused by the many choices on the
shelf. I had extensive experience with the software, so I asked if I could offer some assistance.
They were already talking to a gentleman who also turned out to be a fellow shopper. Over the next
few minutes the other man and I
ascertained the couple’s needs and offered our recommendation. The couple left to buy their
selection, and the other man asked me some questions about me. It was a casual conversation, and we
compared notes on background, training, computer experience, education, etc.
I began to excuse myself when the gentleman asked, “What are you doing now?” I told him I was
reporting to law school next week. His next question caught me off guard: “What kind of money would
it take for you not to go to law school?” I made up what was at that time a ridiculous salary
demand of $90,000 a year. He paused for a second, and said, “I can do that.” He then reintroduced
himself: He was an
executive at a top tech firm, and as far as he was concerned, I’d just had a successful job
interview. Now we were talking compensation packages, and he was making a great offer with a
fantastic career path. I distinctly remember an increase to a six- figure salary after six months.
That would have been amazing for 1992.
I gave it a long thought as it was an extremely tempting offer—he even offered to reimburse me for
all my expenses such as my rent deposit, law-school fees and costs
paid to date, and moving expenses. But I reluctantly refused the very generous offer
and went on to school.
I don’t regret law school or where life took me after that, but I’ve always wondered
how different my life would have been if I had accepted his offer.
John Parziale, Ocala, Fla.
Demetria Gallegos is an editor for The Wall Street Journal in New York. Email her