8 Career Mistakes I Regret Making

As a seasoned corporate recruiter with over 20 years of experience, I’ve seen my fair share of career missteps. Looking back on my own professional journey, I see several decisions and habits I wish I could change.

In this blog post, I’ll share the 8 key mistakes I made early in my career that I now deeply regret—and the lessons I’ve learned that I hope can help guide you to greater success.

1. Winging It Without a Career Strategy

When I first joined the workforce, I had no real plan or strategy for my career. I essentially just “winged it,” without any clear vision of what a successful career should look like. Even before entering the job market, I chose my college major based on the path of least resistance – the one that required the fewest credits to transfer in.

This put me on a fine career trajectory, but not one I was truly passionate about.

Once I started working, I had no idea what steps I should take to advance and achieve my goals. I was just going through the motions without any sense of direction. It’s no surprise that I ended up feeling stuck and falling behind my peers, who were progressing through the ranks much faster.

With the benefit of hindsight, I realize how critical it is to have a clear career strategy from the very beginning. That’s why I’ve since developed a comprehensive course called The Ultimate Career Blueprint. It maps out the key steps you need to take to build a successful, fulfilling career – something I wish I had access to when I was starting out.

2. Spraying and Praying with My Resume

Another mistake I made early on was “spraying and praying” with my resume. Instead of being selective and strategic about the roles I applied for, I would send my resume to any job posting that seemed remotely interesting or promising. My main criteria were: does it pay reasonably well, and does the job title sound decent?

The danger with this approach is that it can lead you to end up in positions that aren’t truly aligned with your long-term career goals and potential. Plus, by blasting your personal information to a wide array of potential employers, you’re exposing yourself to data brokers and the risk of identity theft.

3. Playing It Too Safe

Early in my career, I was extremely risk-averse. I didn’t take many chances or step outside of my comfort zone. I was content just to let the work come to me in my relatively stable, comfortable roles. I even fantasized about switching to something completely different, but I let self-limiting thoughts convince me that I was too far along or too invested in my current path to make a change.

Looking back, I realize that playing it safe in your career is a recipe for mediocrity. If you want to achieve anything truly significant, you have to be willing to take calculated risks and push yourself beyond your boundaries. As I discuss in my video Why a Steady Job is Bad for Your Career, staying in one role for too long can stunt your growth and progress.

4. Tolerating a Toxic Boss

One of my biggest regrets is staying at a job for far too long, during which time I had an extremely unhealthy relationship with my boss. It was a love-hate dynamic – I liked him on some levels, but his behavior was truly toxic and detrimental to my career and mental health.

Despite constantly feeling upset and frustrated, I never stood up for myself or made the difficult decision to leave. I let this person walk all over me, affecting my income and professional development. It took me years to recover from the damage this experience caused.

If you find yourself in a similar situation with a boss who clearly is not looking out for your best interests, my advice is simple: get out. Don’t be afraid to make the hard choice, even if it means leaving a role you’ve invested a lot of time and energy into. Your long-term well-being and career growth are far more important.

5. Waiting Around for a Promotion That Never Came

Another mistake I made was staying in a job where I was constantly being promised a promotion, only to have that carrot dangled just out of reach. The toxic culture of the department I worked in revolved around this endless cycle of setting impossible hoops for employees to jump through, with the promise of advancement that never materialized.

I kept waiting and waiting, thinking that if I just worked hard enough and jumped through all the right hoops, my big break would finally come. But it was all a manipulative game, and my efforts would never be rewarded.

With the clarity of hindsight, I realized I should have stopped wasting my time and energy on this futile pursuit. Instead, I sought a healthier, more supportive environment where my talents and contributions would be recognized and rewarded. Don’t fall into the trap of staying in a role just because you’ve “invested” so much time – your future self will thank you for making the tough choice to move on.

6. Believing My Job Was Irreplaceable

Throughout my early career, I had this persistent mindset that my job was somehow irreplaceable. I would tell myself things like, “I’m being paid a lot to do what I do,” and “I could never find another job that pays as well.” My managers would reinforce this toxic narrative, making me feel like I should be grateful for what I had and not rock the boat.

This led me to stay in roles that were clearly underpaying me compared to my peers simply because I was too afraid to test the job market. I was convinced I couldn’t find another opportunity matching my current compensation and benefits.

But the reality is that there are always other options out there. No single job is truly irreplaceable. Once I finally mustered the courage to explore the market, I realized plenty of companies were willing to pay me what I was worth – and more.

Don’t let fear and self-doubt keep you from pursuing better opportunities that align with your true value and potential.

7. Failing to Negotiate Salary Offers

One of my biggest financial regrets early in my career is that I consistently failed to negotiate my salary offers. Whenever a company presented me with an initial offer, I would accept it without attempting negotiation. My mindset was, “I’m just happy to have the job,” even if the compensation was less than ideal.

As a result, I left thousands of dollars on the table throughout my career. When I later learned what my peers were making, I realized I was being significantly underpaid for the same or similar roles. This compounded over time, as my bonuses, raises, and retirement contributions were all based on that artificially low starting salary.

If I could go back and give my younger self some advice, it would be always to negotiate job offers. Even a small increase in your starting salary can have a massive impact over the long run. That’s why I created the Ultimate Job Seeker Bootcamp, which teaches proven strategies for maximizing your compensation during the offer stage.

8. Feeling Guilty About Taking Time Off

The final major mistake I made early in my career was feeling immense guilt and shame about taking time off, whether it was sick days or vacation time. I worked with many baby boomer colleagues who were total workaholics, and the culture in my department was one of setting the example of perfect attendance.

Whenever I needed to leave work early for a doctor’s appointment or take a sick day, my bosses would look at me disapprovingly and comment. I internalized the message that I was “stealing” from the company and not being a dedicated enough employee. As a result, I rolled over most of my paid time off, never truly taking the breaks I needed to recharge and avoid burnout.

In hindsight, this was a wholly irrational and unhealthy mindset. You aren’t awarded for perfect attendance, especially in a professional, salaried role. Taking time off when needed is essential for your mental and physical well-being—and, ultimately, your long-term career success. I wish I could go back and give my younger self a firm reminder: Take the time off you need, and don’t feel guilty about it.

Lessons Learned and Resources to Help

I deeply regret the mistakes I’ve outlined above, as they held me back from achieving my full potential early in my career. But the good news is, it’s never too late to course-correct and start making more strategic, intentional choices.

If you’re struggling with any of the issues I’ve discussed – whether it’s lack of career direction, ineffective job search tactics, unhealthy work environments, or difficulty negotiating compensation – I encourage you to check out the various resources I’ve created to help:

• The Ultimate Career Blueprint – My comprehensive course that maps out the key steps to build a successful, fulfilling career.
• The Ultimate Job Seeker Bootcamp – In-depth training on navigating the entire job search process, from application to offer negotiation.
• Resume Rocketfuel – Learn how to craft a professional, high-impact resume that gets you noticed.
• Unlocking LinkedIn – Discover how to leverage the power of LinkedIn to skip the recruiter and get directly in front of hiring managers.

My goal is to help you avoid the same pitfalls I experienced and instead empower you to take charge of your career and achieve the success you deserve. With the right mindset, strategy, and tools, you can overcome the obstacles I faced and create the fulfilling, rewarding professional life you envision.

So don’t make the same mistakes I did – learn from them and use that knowledge to propel yourself forward. Your future self will thank you.