a new goal: creating advantages for my boys

Earlier this week, my wife and I sat down to record an episode for a new “show” on AlignedLife about what we’re doing to support Roman, Leo, and Silas as they pursue their Authentic Lives. After the episode, I thought of another way to help the boys—whether it aligns with their Authentic Lives remains to be seen.

I was listening to the Rich Roll podcast with guests Bill Burnett and Dave Evans, who have a new book out, How To Live A Meaningful Life; they also wrote a book back in 2016 called Design Your Life. The conversation centered around the new book and many observations from the Design Your Life course they teach at Stanford. At one point, either Bill or Dave predicted that the most popular degree at Stanford would eventually be poetry or creative writing. He believed that, due to technological advancements, specifically AI, the jobs that most Stanford graduates pursue—Wall Street, tech, law, etc.—won’t have entry-level positions for fresh graduates. If jobs that were once the dream are no longer available, students would choose to pursue something they actually enjoy, such as more creative degrees. There was also a mention of UBI, and while I’m not certain I agree that it will become our reality, I don’t think that changes the possibility of the prediction being right.

The same day, or maybe the next, I read an article called “I Quit” that highlighted some well-known Creatives leaving the professions that brought them fame, success, and financial security to pursue something they were passionate about. The author used this leaving “success” for something more authentic to introduce his thesis that people are opting out of the American Dream because the promises of it are no longer being upheld by the Institution.

“The American Dream was never a simple promise of success. It was a contract. A loyalty agreement between the individual and the system, with terms that were never written down but were understood by everyone who grew up inside them. The terms went something like this: you stay legible, you stay consistent, you defer your gratification, you give the system your most productive years, and in return the system will give you security, status, and the quiet dignity of upward mobility. A house, a pension, the comfort of knowing that your children would have it better than you did, maybe even a gold watch at the end.

It was a room society built and told you to be grateful for. And for a long time, enough people were. The room held. The contract was honored, more or less, for long enough that it has become the architecture of an entire culture—the foundation of how we understood ambition, loyalty, identity, and worth. You were what you did. You were where you worked. You were even, how long you stayed.” - Hezekiah

If the jobs are no longer there and the American Dream contract is no longer being honored, why wouldn’t more people pursue the life they want? At least they’d be doing something they enjoy—and I believe if they are living their Authentic Life, they will be the beneficiary of whatever their version of the American Dream is.

The transition to this new way of living for the masses will take time and will have periods of discomfort. Current graduates are experiencing this discomfort as the employment picture for those entering the workforce is bleaker than it is for those already in it—I believe I heard that the unemployment for recent graduates is above 6%.

I couldn’t help but think about Roman, Leo, and Silas as I listened to the podcast episode and read the article.

I want the boys to pursue their passions. I want the boys to define their definitions of success. As Ang and I discussed, I want to support the boys as they pursue their Authentic Lives.

I also want to give them every advantage I can.

I know there is an argument to be made that our children need to find their way, create their own path, and that parents should provide emotional support and guidance, but to let our children fend for their Selves. I don’t disagree. But I also don’t think I have to let my boys struggle in order to live their Authentic Lives.

So what else can I do to support them as they pursue their Authentic Lives?

I can be intentional about having opportunities for them as they enter the workforce. I’m not talking about handing them a business to run right out of college. I’m talking about them graduating with their first job opportunity, at an entry-level position, ready for them, so they don’t have to take a job they hate or struggle financially right out of college.

Recently, both Roman and Leo have expressed interest in my work at Santiago. I never imagined that my life planning and financial advisory business would one day become a family business—who knows, it still may not. But I will tell you this, knowing that they have an interest in the business has me rethinking how I grow the business over the next 5-10 years. I’ve intentionally built a business that classifies as a “lifestyle business.” I didn’t build it to become the biggest firm or manage the most assets. I didn’t build it to maximize the business's value for an exit. I didn’t build it to have a large team.

I built it to provide a lifestyle, both financially and in quality of life, that allowed me to be very present with my family, support Ang’s entrepreneurial venture, pursue personal growth, take good care of my clients, and not have to worry about finances. I’ve dialed up and also throttled back growth over the years, depending on the stage of life my boys are in, and I’ve always envisioned having a smaller firm in the future to give me more time for my creative endeavors when the boys are all out on their own.

But now that there is a possibility Roman and Leo might want to join me in the future, I’m looking at building Santiago in a way that not only supports the boys and staff that might be necessary for a larger firm, but also a future-proof business model. The good news is that Santiago is already future-proof, and the way I planned to build for the future is too. So my focus really just needs to be on scaling more than I originally planned.

I’m not sure if the boys are really interested in the work I do, or if it’s just easy and convenient to say at this stage of life. For both sports, basketball and soccer, the ideal first job is the ideal first job, and then their fallback would be joining me. If they later determine that life planning and finances are not aligned with their Authentic Lives, I plan to continue building my creative collective PRST as another option for them. PRST will have opportunities in podcasting, film, clothing, events, and more—again, not opportunities to take anything over, but entry-level positions to grow from.

And if Roman, Leo, and Silas decide they don’t want or need the opportunities I'm building for them, that’s ok. Don’t get me wrong, I’d love to work alongside my entire family, but I’m not changing my vision for what I’m building to make sure that happens; I just want to know I can help them if they need it.

One of the benefits I’ve gained by taking an entrepreneurial path is that I can create whatever I want. And while it is a tremendous privilege to one day give my boys an advantage in life, it’s one I’ve worked hard to create.

In addition to everything Ang and I discussed on the podcast, another way I can support my boys as they pursue their Authentic Life is to do my best to give them an advantage they wouldn’t have without me.

And once the advantage is in their hands, the rest is up to them.

Keep pursuing,

JC