When you hit your 40s, there aren’t as many “firsts” in your life as there used to be. First kiss, speeding ticket, job, first time traveling abroad, first child…a lot of life’s firsts are in the rearview mirror.
There was one “first” that I was happy not to have experienced to this point in my life – losing my job – that is, until late last year. It was surprising, disappointing, and scary.
I always tell my kids we get better at what we practice. Well, I had no practice being unemployed, so it should come as no surprise that I wasn’t well equipped to manage the reality and emotions that came with a sudden job loss.
I wasn’t in a particularly desirable position when I lost my job (then again, is anyone ever?). I was recently divorced and my two kids live with me half the time. So when I was let go, one income to cover our household expenses turned into none.

I also knew that jobs for people with twenty years of work experience don’t grow on trees, so it could be a minute before I found something new. Add to the fact that being divorced with kids meant that relocating wasn’t an option I’d consider – the best job title I’ve ever held is “dad” – which meant my job pool was even smaller.
Below are 12 lessons I learned from losing my job. Some are related to investing, and some are related to life. I hope that they resonate with you wherever you are on your life journey and whatever struggle you might be enduring today.
1) Practice Makes Progress – It’s an axiom I use with clients and my kids. Whether you’re facing a job loss or retirement, disciplined investors have a LOT of practice at accumulating savings – years or decades. But most investors have no practice at taking distributions from their savings. I have savings for unexpected events such as a job loss. But I wasn’t prepared for how I would feel about spending that savings. As my final paycheck loomed, I felt increased anxiety about tapping my savings. What was the best solution? Do like Nike and “just do it.”
I bled a lot before I was cut by the idea of withdrawing money from my savings. Taking a distribution and realizing that the sky wasn’t falling was the best thing for me. Retirees can have similar feelings when the income tap from a job runs dry. In both cases, having an impartial financial planner to help you manage your emotions and finances can be supremely helpful.
2) The Meaning of Your Story – Life isn’t about what happens to us but the meaning we give it. When a parent dies, one child can be bitter that they died too young, while the other can be grateful for their time together. One experience → two completely different meanings.
Did being laid off happen to me or FOR me? Is my life falling apart or falling into place? Is it a setback or a set-up? Self-made billionaire Jamie Kern Lima wrote in her book “Worthy” (that I read while being jobless) that she believes rejection is God’s protection.
History is littered with stories of super-successful people succeeding after failure. “Failure is just life trying to move us in another direction,” as Oprah reminds us. During my job-free time, I reminded myself regularly that faith is believing in something that hasn’t happened yet.
3) Grief Can Lead to Gratitude – Do you know who enjoys a hamburger the most? The person who’s gone without one before. Who enjoys a paycheck the most? Those who have experienced what it’s like not to have one.
There’s a reason why people who have survived cancer often have a newfound perspective on life. Going through hard times like death, divorce, or job loss can frequently lead to an attitude of gratitude because we no longer take life (or all the small things that make it great) for granted.
Despite my job misfortune, I was blessed to be able to remain in my home with my two healthy, wonderful kids with food on the table and friends and family nearby for support.

4) Choose Your Hard – Have you ever complained about having to go to work on Monday? Yeah, me neither… Having a job can leave you feeling stressed, overwhelmed, and burnt out as you try to juggle the work/life balance. Having a job can be hard.
But not knowing when you’ll be employed again, when the endless networking will pay off, or how low your savings will go is hard, too. Sometimes, when we feel that life is hard, it’s valuable to step back and realize that the alternative is hard (and maybe harder), too. Speaking firsthand, marriage is hard, and divorce is hard, too. Having to go to work on Monday is a problem I look forward to having again.
5) The Kindness of Others – Most media has a negative slant because people tend to watch or read longer. If it bleeds, it leads, so they say.
Since I lost my job, I’ve met with dozens and dozens of people. I’ve been astounded by how many people have been willing to meet, connect me to people in their network, share their wisdom, and even insist on picking up the tab for coffee or lunch. Time after time, people went well out of their way to help me when I had nothing to offer them in return. Most media focuses on the negative, but most people are good – better than good.
6) Networking Isn’t a Dirty Word – I used to dislike the idea of networking because it felt like doing an activity to get something in return. It felt inauthentic or too quid pro quo-ish. Recently, a mentor said to think of your network as professional friends, and that meaning helped me reframe the idea of networking. Through this job search, strangers and professional acquaintances have become dear friends – a pleasant surprise from an undesirable situation.
7) Starting Something New – “If necessity is the mother of invention, discontent is the father of progress,” as David Rockefeller says. I’ve been writing weekly as part of my job for the past 8 years in my Chief Investment Officer role. Call it necessity or discontent, but I wouldn’t have started this blog had I not lost my job. Many successful companies have their origin in downturns or recessions. This blog has been a gift in so many ways but most importantly, allowing me to do what I love helping others achieve their financial goals. Sometimes, our best ideas or creations come from our hardest moments in life.
8) Expect To Reinvent Yourself – A mentor I met during this journey shared this sage wisdom: throughout your career, you will have to reinvent yourself. I’ve experienced this firsthand, spending the first portion of my career as a bond trader before transitioning to a Chief Investment Officer role. My next role will require a similar reinvention. Having proper expectations when navigating new waters of life can make a big mental difference. Change is the only certainty in life.
9) Make Sure You Have the Right Tools – Going through a job loss is hard and upends many parts of your life. The same goes for death, divorce, sickness, etc. The right tools to deal with these changes can make all the difference. Ironically, going through a divorce before losing my job taught me the tools I would need to navigate this difficult time:
- Give yourself grace and self-compassion – What you’re going through is really hard. I didn’t understand grace or self-compassion before my divorce.
- Lean on friends and family – Talk to people. Shame can’t survive being spoken, and if you don’t own your story, your story owns you.
- Exercise – Moving your body has tremendous benefits for your physical and mental state. As a bonus, I’ve found exercising reminds my brain that I can do hard things, an invaluable reminder when going through struggle in life.
- Rely on experts – A therapist or outplacement coach can be a terrific investment and made a massive difference for me, personally. Understanding grief and how it impacts you through books like “Life After Loss” also helps make the emotional valleys shorter and shallower.
- Expect challenging days – Didn’t make the cut for final interviews or annoyed about attending your 35th networking coffee? That’s normal. People don’t drown from falling in the water; they drown from staying there. Give yourself grace and feel those feelings and then get out of the water. You’re doing better than you think you are.
- Volunteer or help others – It’s hard to feel helpless when you’re being helpful.
10) Pain + Reflection = Progress – Everyone says they want to grow but the truth is growth isn’t fun in the moment. It looks more like struggling, failing, and trying again. When you’re having a hard time, recognize that growth is hard and doesn’t feel like growth in the moment. Like preparing a good home-cooked meal, you have to wait until the end to enjoy it.
11) Put your Budget on a Diet and Review Your Financial Plan – After I lost my job, I replaced my house cleaner and hired myself. I didn’t do as good of a job, but I was much more affordable. Reviewing unnecessary expenses like subscriptions is a good annual practice particularly after a job loss.
Also, don’t be like me. I had 6-12 months of savings for unexpected life events but it wasn’t all in liquid, safe investments such as cash, CDs, or bonds. Not smart, especially for a one-income household. I was lucky that the strong stock market last year allowed me to sell stocks without locking in losses at my time of need. Do as I say, not as I did.
12) Who’s Watching You? Recently, I asked my 7-year-old son if he thought adults have problems. He said no. After initially sheltering them from my unemployment, I realized that I needed to share this experience with my kids. By sharing my struggles, they could see that it was okay for them to struggle, too. I could talk to them about the tools in lesson #9 above that I was using to take care of myself. They could understand why I teach them to save some of every allowance (paycheck), which allowed us to stay in our home with food on the table.
By sharing with them, they could learn that it’s possible to come out of struggles better on the other side. After all, lessons are caught, not taught – monkey see, monkey do. When you’re going through a hard time, you never know who’s watching you, learning from you, and being inspired by you.
Every end is a new beginning. The older I get, the more convinced I am that God will use our greatest pains in life to serve others. I’m beyond grateful for all those people who helped me navigate this challenging season of life, it’s meant more than words can explain. A true gift is one that can’t be repaid.
As my unemployed time nears an end, I hope these lessons from losing my job will serve me and others well in the future. This post is the first step.
Please consider sharing this post with those who might need to hear these words. Reaching out to people when they’re struggling is one of the kindest things you can do, and they won’t forget it – and neither will you.
Castle Quote: “The loss of a job may be the wake up call needed to redeem the fire of your genius.” – Dan Miller

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