Life Coaching

Like many people in their mid-thirties, I’m starting to wake up and realize I don’t know everything. I may have said this sort of phrase in my twenties, but not until recently have I begun to mean it. Perhaps you can relate.

And it’s not like we didn’t have people telling us this along the way. Parents, sports coaches, teachers, music instructors, etc. that have poured into us are the most amazing people we know. (Seriously, as I think about it, I have many people to thank!)

During the most intense seasons of life, I have personally had the privilege of having regular calls with “Life Coaches” — i.e. people who help provide a framework for thinking about life (not just work). They hold me accountable as I strive toward self-defined goals, and they climb into the trenches with me to contemplate the “why” and “how” behind time management and prioritizing ToDos.

Interestingly, the best life coaches rarely give advice; instead, they help discover the intersection of passions, skills, and what their clients care about most.

Over the past six years or so I’ve had the privilege of “paying it forward” by coaching young startup founders and CEOs. I often talk about what I call The Eight Buckets — i.e. being deliberate about your worldview, relationships, health, finances, work, volunteering, vacations, and hobbies (in that order!).

#1. Worldview

German philosophers call it a weltanschauung — i.e. welt (‘world’) and anschauung (‘view’ or ‘outlook’), and I appreciate how wikipedia succinctly defines it:

the framework of ideas and beliefs forming a global description through which an individual, group or culture watches and interprets the world and interacts with it.

Of particular importance is personal awareness of the lenses and cultural influences through which you see the world. The environment you grew up in —i.e. your family, friends, teachers, authors/speakers you listened to, games you played, rules and laws you abided by (or didn’t), movies you watched, etc… — had a profound effect in shaping who you are and how you perceive reality.

In general, at this level, there are two things I usually camp on:

The first is to identity what dogma you believe — i.e. the non-scientific stuff that has been passed down to you (and is currently being fed to you) via the influencers in your life. Whether it is right-leaning or left-leaning politics, religion, philosophy, sociology, etc… all of us believe dogma to some degree or another. It’s unavoidable. The best we can do is be aware of it and try to believe the healthiest things possible.

The second thing I camp on, which is related, is to ensure that no matter what worldview you pick, be sure to pick one that that leads you toward empathy, compassion, and generosity. You may be rolling your eyes at this point, but with depression and mental illness as a serious and growing issue amongst startup founders — i.e. the people I work most closely with — I’ve found that it’s important to bring up these issues early and often.

Being mindful of your levels of empathy, compassion, and generosity toward others is one of the most time-tested recipes of happiness there is. No one nails it, but the more we talk about it and hold each other accountable, the better.

#2. Relationships

Who you choose to spend your time with, especially your closest family members and friends, should be your first priority after cultivating a healthy worldview.

Are you spending enough time with your significant other, kids, siblings, and close friends? Are you calling your mom and dad enough? Just talking about this with founders usually brings to mind a zillion ToDos; the importance of this bucket is hard to overstate.

When the sh*t hits the fan, and life inevitably happens, these are the people who will be caring for you. Likewise, hopefully these are the people you will drop everything for when it happens to them.

#3. Health

Both mental and physical. Seriously, when was the last time you went to the doctor and got data about how you’re doing? When was the last time you saw a mental health professional?

If you are the kind of person that has read this far in the article, then I can almost guarantee you need therapy (not even joking). A life coach isn’t your therapist; a life coach helps you realize that you should see one.

Likewise, do you understand how sleep, cardiovascular exercise, weight lifting, carbs/fats/protein/vitamins/minerals/fiber/hydration, etc… affect you? If not, you have some serious homework and self-experimenting to do.

#4. Finances

On the list of life stresses, this one is right up there with relationships and health. Therefore, it also needs to be prioritized over work.

As of Q4 2015, the average american household has $15,762 in credit card debt, and $48,172 in student loan debt.

If you are an average american, I’d strongly advise that you seek out financial coaching. What you’ll learn about are the latest best practices for consolidating and paying off debt, setting realistic budgets, building a strategy for saving/investing, and balancing cash flow with the cost of your desired lifestyle.

Not surprisingly, many founders are attempting to grow businesses without first taking care of their own household. The best founders I’ve seen, regardless of their personal situation, are diligent about learning everything they can and putting into practice healthy financial habits. You can’t just expect to hire “a finance person” to take care of all your startup problems.

#5. Work

Most people spend very little time being diligent about buckets 1–4 above, and instead plow most of their time into their work. This, in turn, usually causes health and relational problems.

Likewise, while you’d think making more money will solve financial issues, increases in income are usually coupled with increasing personal burn rates, and thus “the rat race” ensues. It’s hard to get out of it unless you quickly make an extraordinarily large amount of money (i.e. rarely happens) or if you adjust down your cost of living (also rarely happens, but this is obviously more in your control).

According to Deloitte’s Shift Index Survey, well over 80% of people in the USA are dissatisfied with their work. Ouch. The obvious advice here is to find work that intersects with your passion and talent, but that is easier said than done. It’s safe to say that most adults I know are thinking about leaving their jobs, and a good fraction of those people would love to jump into startup life but haven’t (yet) pulled the trigger.

In general, it’s best to NOT leave your day job, and instead focus on doing amazing work and making your boss as much money as possible. For most people, this will lead to more happiness than quitting and finding another job, or trying to launch a business that will most likely not support you financially. For everyone else, you are the type of person that will quit the job and start the business anyway, so it’s best to get as far as you can with your new business before you make the leap.

#6. Volunteering

Before we talk about vacations and hobbies, let’s talk about being deliberate with your time to help other people.

Take a look around. What non-profits are doing work in your community that you care about? Have you reached out and asked how you can help? More than just receiving funds, all non-profits appreciate smart volunteers that actually show up and are willing to be in it for the long-haul.

Don’t make the mistake in thinking that if you give financially to causes you believe in that you are doing your part. They need your time and mental energy as well.

Since it’s easy to forget about volunteering and spend most of your non-work time pursuing hobbies, it’s best to first figure out where you are going to plug in and help, then schedule this time deliberately in your calendar so you are mentally prepared to serve (i.e. so it doesn’t sneak up on you and you end up skipping it).

#7. Vacations

It works best to schedule —well in advance — one main vacation every quarter (even if it’s short). As life moves along and a significant other and kids enter the picture, it gets increasingly important to establish yearly rhythms (e.g. at least one week alone with your significant other, a couple family-only vacations, and one with a larger group of friends).

Vacations are also a great time to cultivate your worldview and relationships buckets, and set a plan for your health, finances, work, and volunteering. Taking into account all of this, I then usually try to plan vacations around hobbies (e.g. kiteboarding, skiing, and fly fishing), since on a practical level I don’t get to do those very much and find that if I don’t book a trip around them they won’t happen.

#8. Hobbies

Yes, these come last in terms of priority. Hobbies should fit into the margins of your daily, weekly, monthly, quarterly, and yearly rhythms and be used in parallel with as many of the other seven buckets as possible (e.g. hiking with a friend).

Counterintuitively, if you prioritize hobbies this way then you’ll be a happier person, since all of the more important things in life are in order.

Now, that being said, hobbies are a hugely important part of life and deserve a bucket along side the others. Humans don’t function well unless we can do fun things on occasion, especially with our friends.

The Pursuit of Happiness

In closing, I recently watched a documentary from 2011 called Happy and have been thinking about it every day since. In collaboration with scientists, the filmmakers surveyed people around the world in various financial, social, and environmental conditions and found what made people happy across the board — not at all correlated to money — were the following seven things:

  1. A close community of family and friends
  2. Helping people
  3. Getting into the state of “flow” often
  4. Doing meaningful work
  5. Having variable experiences (notably outdoor ones)
  6. Getting to play
  7. Appreciating what you have

I’ve recently started framing my morning journal time with these seven points superimposed onto the eight buckets. This framework leads to an infinite number of things to write about, and helps reveal the most important ToDos to accomplish for the day and week. The key is to put these ToDos on your calendar at specific times when you’ll commit to actually getting them done.

If you are interested in life coaching, ask your friends for a recommendation (you’ll be surprised how many people have secretly been hiring life coaches for years!). Feel free to ping me as well (will@protaventures.com); I’m taking on a couple more clients and have good friends who I can recommend for the job as well.

If you are already a life coach, let me know if you’d be interested in teaming up with us at Prota Ventures (i.e. the venture building and early stage investment firm I manage). My partners and I are considering spinning up a life coaching business and a set of products related to helping people self- and peer-to-peer coach.

Regardless, I hope that the above strategy can be helpful to you in some way as you think about how to plan your life and prioritize ToDos. If you’ve found this article useful, or if you have any comments/suggestions, I’d love to hear about it.

Author’s note: my main writing projects at the moment are books about idea-to-funding startup operations and web/mobile development for aspiring technical founders. Feel free to subscribe to my newsletter and I’ll let you know when I get new content up; and/or click “Follow” below to stay updated by the good folks at Medium. Thanks!