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Navigating the Complexities of Re-entering the Workforce After Long-Term Retirement

If you’ve been retired for a while and are thinking about rejoining the workforce, you might find it more challenging than you expect. I’ve been there, and I want to share my experiences to help others navigate this tricky path.

I retired early, and for a while, I was a full-time dad. I loved every minute of it, especially during the pandemic when my kids needed me the most. But now, my oldest is in first grade, and my youngest will be starting preschool full-time in the fall of 2024. So, it’s time for me to dust off my resume and start job hunting.

Don’t get me wrong, I don’t regret choosing family over career. But, I won’t lie, the thought of the millions I could have earned since 2012 does cross my mind. Plus, with college tuition looming in the future, a little extra income wouldn’t hurt.

I’ve been writing consistently for Financial Samurai since my retirement in 2012, so it’s not like I’ve been completely out of the loop. But, it’s been eight years since I did any part-time consulting, and that’s the closest I’ve come to traditional work.

Here are some of the challenges I’ve faced in my job hunt:

  1. Lack of Connections: When you’re out of the workforce for a while, your professional network tends to dwindle. It’s harder to get referrals, which are often the key to landing coveted jobs. My advice? Keep in touch with your industry peers even after retirement.

  2. Age Discrimination: I left work when I was 34, and now I’m 47. Ageism is real, and it’s something I’ve had to grapple with during my job search. My advice? If demographic surveys are optional, skip them.

  3. Fierce Competition: I’ve been considering working in the AI sector, but the competition is intense. My advice? Look for up-and-coming companies and sectors, or consider lower-tier companies that aren’t as popular.

  4. Salary Expectations: I used to earn a base salary of $250,000, and I’m not willing to settle for less. This limits the number of jobs I can apply for. My advice? Consider the trade-off between pay, job experience, and work-life balance.

  5. Job Hunting is a Numbers Game: The more jobs you apply for, the higher your chances of landing an interview and eventually an offer. My advice? Apply for as many jobs as possible and don’t be discouraged by rejections.

I live in San Francisco, a hub for AI companies. But, I’ve failed to build a network in this sector, and I didn’t recognize the potential of AI until recently. So, I need to start networking and learning more about the industry.

In the meantime, I’m investing in AI through venture capital funds. If I can’t land a job in AI, at least I’ll have some exposure to the sector.

If you’re considering early retirement, I recommend keeping your skills and connections fresh. Consult part-time, or alternate between periods of retirement and full-time work. After three years out of work, it becomes significantly harder to find a job at a similar level and pay to your previous role.

I’m still on my job hunt, and I have until fall 2024 to find the ideal AI job. If I don’t succeed, at least I can tell my kids that I tried. And who knows? Maybe the future holds something even better for me.

If you’ve been in a similar situation, I’d love to hear your experiences and advice. And if you work at an AI company and could give me an introduction, I’d be grateful.

Remember, whether you’re considering early retirement or looking to rejoin the workforce, it’s important to keep your options open and stay connected.

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