Joys and Regrets of My Twenties

Reflecting on my twenties from the vantage point of forty

Meg Jay's book, The Defining Decade, for and about twentysomethings is excellent. She has street cred as a psychotherapist who has worked with dozens of twentysomethings in the San Francisco bay area and on the East Coast. Her book is filled with real-life twentysomething case studies I've heard many times before as a pastor who works with young adults. My first exposure to Jay came her through her excellent TED talk and then a friend loaned me her book. The gist of it goes something like this: 

Stop putting off your most important decisions in your twenties. The life you envision will not happen overnight so start planning and working on it today. 

It probably takes at least ten years of distance to determine whether a major decision you made turned out well. So as a forty-year old, I decided to look back on my twenties and evaluate the life choices that gave me the greatest joys and those that gave me the greatest grief.

Biggest Joys

1) Being ministry-minded: When I became a follower of Jesus at thirteen, it never occurred to me that Christianity was intended to be a spectator sport. I didn't understand how Jesus could die for you and that not affect the way you live. Perhaps it's because I didn't grow up in a Christian family and when my parents became believers at the same time I did (forty-one years old!), their transformation was gradual yet dramatic. It left a deep impression on me that being a follower of Jesus meant obedience and laying down one's life. Otherwise why bother? 

My parents, brother, and I helped plant my previous church, CCIC-SV, twenty-four years ago. Almost immediately, my brother and I began leading the youth group. From that point on, I don't remember ever not being part of Christian leadership. Jay writes about taking work and career seriously.   It means doing interesting things in your twenties ("building identity capital" she calls it) that challenge you and help you write a better story. My nine-year tech career shaped my ministry story in ways that vocational ministry could not. And ministry is the best story. 

2) Learning from mentors: The greatest contributor to my ministry-mindedness was the role of disciple-makers. My first mentor played basketball with me while I was in high school. We went on a couple missions trips together and he was one of the best models of discipleship I could ask for. Finding mentors during college and the first couple post-grad years was easy because so many resources are focused on twenty-somethings. It became tougher after I got married and had kids (it's even harder in your thirties but that's for another post). But apart from being ministry-minded, no other set of decisions has had a bigger impact on my life. In fact, it is disciple-makers who shaped me to be ministry-minded, shaped my trajectory of life, and influenced my view of marriage. Even my corporate career benefited from mentoring. I didn't know such a thing existed until I was assigned one. My mentor's investment helped me become an almost competent project manager. My mentors gave me a grid with which to evaluate the most important things in life. They taught me what was the highest priority and modeled and encouraged me to live accordingly.

I find it puzzling Jay doesn't write more explicitly about this. She mentions the power of weak ties, which are valuable at every decade but I find it curious she doesn't talk about the importance of mentoring as she plays that role for her twentysomething clients. I would recommend every twentysomething have at least two older friends who are not in their twenties and at a point in life where you want to be at their age.

3) Marrying a ministry-minded person early: You might think this should be at the top of my twenties' joys. In terms of personal happiness, it certainly may be highest. But the first two joys set me up for the third. Being ministry-minded meant a rapid ascent into leadership at Cru (formerly Campus Crusade of Christ) in Berkeley. Leadership meant I received mentoring by older college students and Cru staff. These men had a profound impact on me. We talked about dating and marriage all the time. It was embedded in the culture of our campus fellowship. And as part of my ministry-mindset, I found myself living in the same dorm with other Cru women during my junior year. I led a men's Bible study and the Cru women led a women's Bible study. Two years later, one of the female leaders would become my wife.

One of Jay's points about one's twenties is seeking first what's most important. Who you marry carries far more weight in determining your lifelong personal fulfillment than your career. My mentors told me that before I entered my twenties, and I'm so glad I listened. And yet the majority of Jay's twentysomething clients want to postpone mating for career. And due to our culture's romanticism, they're simply not as thoughtful and intentional about mating as they are regarding work.

If you want to be married by thirty then don't wait until you're twenty-nine and expect it to happen in a year. My late-teens set up my twenties. I began thinking seriously about marriage right when I started college at eighteen. Even though I got married at twenty-three, I had already been contemplating marriage for five years. People have commented our courtship was serendipitous. Certainly. And yet I had a pretty good idea that marriage was an important calling, what qualities were non-negotiable in a spouse, that Judy had those qualities, and finally, that I should not balk at pursuing her. If you're in your twenties and you want to get married by thirty, stop the shenanigans and get serious. If you don't know how to do that, start with 1) and 2). 

4) Having kids early and seeing them as a ministry: Most people don't want to be parents in their twenties because kids limit personal freedom and are hard work. But if you view children through a ministry mindset, then, just like marriage, having kids is something that is worth giving up freedom for.

Caleb was born when I was twenty-six. The others came about every two years or so. It's tremendously enjoyable to be a dad. I love that I have the energy to appreciate my kids to the fullest extent. I love the stage they're at now and I love that I still can keep up with them (when I'm uninjured). I love to talk with them about life and the books they're reading. I have great memories of dinners laughing together, playing Just Dance, throwing them around in the swimming pool.

Having a ministry-mindset helped me avoid the temptation of idolizing my children. I see many parents make children the sun in their universe and they are orbiting planets. If that's the way to raise children, it's no wonder families delay having kids. Jesus is the sun, my wife and I are planets, and our kids begin as moons that grow to become sun-orbiting bodies.

Here's a couple more perspectives Jay offers on having children: First, a woman's fertility is bounded by time. It peaks during the twenties and then gradually declines until the mid-thirties, when the drop steepens. I love that Jay has the courage to address this unpopular, anti-feminist notion. You can certainly find exceptions among celebrities but it's not something to roll the dice with and not everyone has $50K to spend on multiple IVF treatments. Second, one of the greatest gifts you can give your parents is grandchildren. Some people don't want to give anything to their parents but as the child of immigrant parents who slaved to give me a better life, having kids has been a joy to both Judy and me AND our parents. Jay writes:

There is something profoundly sad about seeing an eighty-year old grandmother come to the hospital to meet a grandchild. It is crushing to realize there won't be many sunny days at the lake with Grandpa or holidays spent in Grandma's loving presence. It feels almost wrong to look at our children and wonder how long they will have their grandparents in their lives - or even how long they will have us.

Biggest Regrets

1) Investing my worth in my job: I worked too much. I thought my job was important. I thought the quality of my work, the number of emails I received, and the status of my position indicated how significant I was. I worked long hours not because I knew otherwise, at least intellectually.  I read Search for Significance and other books about the gospel and knew that my worth wasn't found in my work but I couldn't overcome that in my heart. I honestly don't know how I could have overcome this as I'm twenty years into working life and I still struggle with finding my worth in my job. It is part of the curse. The consequences of this mindset affected my marriage, my relationships, my ministry, and my contentment. I can recall moments when I missed out on vacations or was emotionally absent from Judy or the kids because I couldn't stop thinking about my job.

The one thing I might have done differently is establish better boundaries around my work. I don't know how to stop working and I wish I had done a better job turning myself off. I recognize now it's an integral part of my personality - I tend to work too hard rather than not hard enough. What's interesting is that I could have worked fewer hours and done just as well but I would stay at work because I felt guilty for not getting more done and ashamed at leaving the office earlier than other people. I would waste time surfing the web because I was anxious about certain tasks and would put them off for the end of the day. It was a bad cycle.

2) Taking friendships for granted: Friendships came easily during my early twenties. College was an oasis of friendships. I could afford to be picky about who I spent time with. And yet somehow close friendships eluded me. When I started to get close to someone, I would get bored and move onto someone else. I would bemoan the fact I didn't have close friendships like my brother but it was me that was the problem. It was Judy who repeatedly pointed out this pattern to me but I didn't start to change until my thirties.

When Judy and I first got married, we experienced a rapid drop-off in our friendship circles. We simply weren't as available to hang out, had few friends that were married, and were not interested in what our single friends were doing (my guy friends were playing a lot of video games). When we had kids, the drop-off was much more severe. At that point, it didn't feel like we had a choice, we had to turn down social invitations. In my thirties, I began to have much more gratitude for friendships. You don't know whatcha got 'til it's gone.

Lastly, as part of this friendship regret, I was reluctant to seek marital counsel when our marriage became strained. Judy and I waited until things were really bad between us before asking for help. It's not easy to recognize a marriage need help because the negative patterns don't appear instantly - they gradually introduce themselves over the years. And they're never a mystery - it feels like you could overcome them if you tried harder or had a different perspective but somehow you're never able to do it on your own.

3) Living conservatively for the kingdom: I wish Judy and I had taken ourselves less seriously and planned more spontaneous trips together. I wish I had taken bigger risks for the kingdom of God. I wish we could have done an extended ministry trip or vacation together. I wish I had spent more time with Judy our first year of marriage and really enjoyed her. We could have built a stronger foundation of memories and affection before we had children. It's not too late but it's harder to do now. I wish I had eaten out less and been more generous with our money. I wish I had taken more risks in living out the gospel to my IBM/Hitachi coworkers. I wish I had failed more so that failure wouldn't have been so humbling when it happened to me in my thirties. If I had learned to fail well, it would have helped me develop courage but instead, I often played it safe. 

4) Seeing my interests and work experience as meaningless: I spent nine years out of college as a business analyst and project manager at IBM and Hitachi. I distinctly recall working on step forms and process flows and feeling dismayed that this was what my life had come to - copying and pasting data fields and moving symbols around on a diagram. I hated doing that stuff. I thought work should be constantly exciting and creative. Looking back, those were my Karate Kid moments. It was like Miyagi-san teaching Daniel how to wax on and wax off. The discipline, skills, and perspective that helped me crank out work has helped me slog through tedious work today (and every job has tedium), helped me be detail-oriented, and honed my critical thinking skills.   

As a kid, I loved playing with LEGOs, reading, singing, dancing, and daydreaming. I never thought those interests would amount to anything. Now I see how those interests have shaped me as a communicator of God's Word. My love for books and learning is a boon to my preaching and teaching. My critical thinking skills have helped me understand people's hearts. And my kids' love for musicals stems from my love of music and dancing. Your interests and dreams matter - perhaps not in the way you think - but they matter for the kingdom and God wants to use them.

What are your joys and regrets from decisions you made a decade ago?