I’ve been living my life in seven year chunks since I was 24 and began my career in earnest. I work hard for six years and attempt to rest in the seventh year (to varying degrees of success), recalibrate and refocus. It is a practice that dates back thousands of years but isn’t followed much anymore. I find there is often wisdom in old traditions though.

Back at the end of 2018 I wrote a vision for the next seven years of my life (actually 7.5 years since I decided to shift the start from mid-year to align with the calendar year). I had realized that most of the people I studied had their greatest impact later in life, and that to achieve similar things, I should spend some time focusing on preparations with the long term in mind. Even if I did not know what that long term involved.

Now, at the end of this period, I want to think back and reflect on it.

I wrote in that post that I wanted to spend time during this period developing my character, becoming an expert at topics I was passionate about, demonstrating my ability to execute on a tactical level, building up my financial savings, forming key relationships and set up circumstances that would allow me to flourish later in life.

Overall this period has been a success. If when writing that blog post I could glimpse the future that I sit in today, I think I would be quite satisfied. A lot of this comes down to three or four decisions which turned out close to ideal, but some of it comes down to 2,750 days of waking up and trying to do things just a bit better than the day before. It adds up.

When I named this period, I called out a few specific things that I might try to achieve. Looking at those will be a good structure to guide my reflections.

Forming relationships with mentors that will help guide me

This might be one of my weaker areas. I haven’t formed what I would consider any formal mentorships and most of my relationships of the learning type are in my professional sphere. It would perhaps behoove me to have some mentors in the sphere I intend to spend most of the remaining years of my life in – if I knew what that was.

I do have a number of managers that I consider mentors. Folks I stay in touch with and try to learn from. It is always invaluable when someone has a higher horizon and can see over the hill you are facing that looks insurmountable to you, but that they see as only a speed bump.

Identifying comrades in arms for missions I believe are important

I have had middling success here. I have been able to form a lot of peer relationships in various spheres with people I really enjoy and who I share certain overlap in beliefs with.

As is perhaps expected, the circles are usually not overlapping. I know a lot of great software engineers and PMs who I could start a tech company with, but I might struggle to find any that would go all in on a cause with me if there wasn’t a financial upside. I know a lot of people who I can get to volunteer to clean a homeless shelter or coach individuals incarcerated in prison, though not all of them have the ability to devote more than a couple of hours a month to that.

What I think stands out the most is that in the areas I have spent time, I have found comrades. Perhaps as I gel on the areas I want to spend more of my time, I’ll be able to repeat the process of establishing relationships in that domain.

Investing in key skills that I can leverage later

I have picked up a few skills over this period

• I entered with some ability to excel in areas I was familiar and I leave having gained the ability to quickly learn new areas and how to thrive in them.
• I entered it having run a marathon and knowing I could work hard for three hours and I leave it having done some endurance feats that showed me I can sustain that for days
• I entered knowing a bit about how to keep to a budget and I leave having spent a lot of time learning about investing in different classes of assets and using options as hedges
• I entered being able to give a presentation to a small group and I leave being comfortable (perhaps even captivating) in front of audiences of up to a thousand people or a smaller group of very senior folks like the C-Suite of a public company
• I entered with the ability to say yes to some good things and I leave with the ability to say no to some very good things, to defend the space for the few items that are even more important

Identifying topics I want to specialize in & becoming an expert

I somewhat accidentally became an expert at consumption based monetization, enterprise software, cloud infrastructure and operating as a manager in a big technology company. Those skills are quite specific, though in a way that self-selects for being adjacent to success. I could not have guessed when I wrote that blog post that I would know anything about these topics – I didn’t even really know they existed.

I have spent a lot of time in two areas over the past few years though that really interest me and that I can see being a big part of my life going forward. The first is using fitness activities as a way to build community – something I’ve learned by joining and helping start some free neighborhood workouts. The second is using business skills as a way to help people imagine their best self – something I’ve learned in my time volunteering in a nearby prison.

Demonstrating the ability to execute exceptionally on projects of increasing scope

I entered these years able to be a leader on a project that included a few individuals and I leave it having developed the skill of organizing and motivating on the scale of hundreds of people. I entered able to work on the scale of millions of dollars and leave comfortable with the scale of billions.

Building up financial basis that allows me more opportunity later

One thing I’ve talked about for a long time wanting to save enough money while working in a fast-paced tech environment that I did not necessarily have to do that forever. The option value of being able to decide to do something else. I’ve spent a decent bit of time in my life volunteering with causes I think are important and I like the idea of being able to do more of that, rather than always having to focus my attention on OKRs, new product launches and winning the next big deal.

I focused on that during this chapter and kept disciplined about saving. Now I have a bit of freedom thanks to that.

Setting up circumstances so I am close to an ideal place for later action

This one largely depends on what that later action is. If it involves the cloud or enterprise technology space, I think I’m in about an ideal place as possible. If it were getting elected to the house of representatives, I think I’d have more trouble – perhaps I could navigate that transition though.

Building credibility with the types of people I will need support from later, even those I don’t personally know

If I would have asked for a few million dollars to attempt to start a business of some sort a decade ago, I think I would have struggled to come up with it. I don’t think I’ll have trouble with that anymore. Some of it is that I directly know a lot more people who have some money to invest at a high risk threshold and who also believe me being a part of the investment lowers the risk. Some of it is that the people that I know are connected to an even bigger group. At this point I bet I’m only two or three hops from an email intro with anyone in tech. Finally, some of it is that my resume now says Product Manager from Google and Databricks – that goes a decently long way at opening up doors.

Access to capital isn’t everything, though it certainly a lot since capital often comes with buy in and assistance. Some of the value of a big network of trust is the doors it opens, acceptance of an introductory meeting, admittance into partner programs, early access to integrations, strategic partnerships, etc. Those things don’t go very far if there isn’t some value to back it up, but that is where I lean on the categories I talked about above like skills and comrades in arms.

Conclusion

Looking back, this period has accomplished what I originally hoped it would. It put me in a place where my future is fairly wide open with possibility. It took a lot of hard work and a bit of luck, but overall I am pretty satisfied with how things turned out and excited to embark on the next sabbath cycle.