The Quarterly Review (Career Planning for Entrepreneurs)

Quarterly Review

h/t to Taylor Pearson for this format. I’ve previously written about my morning routine. Using resources from Taylor’s new book, The End of Jobs, I’ve expanded this into a 4 part series:

It’s not very helpful to “plan”—break things down into action steps— on a longer time frame, but keeping the destination in mind when I review and plan lets me manage my motivation and goals more effectively. I can see how everything I do on a day-to-day basis is taking me towards where I want to go or if they aren’t taking me there, stop doing them!

Review and Update Your “Perfect Day”

If you could do anything without chance of failure, what would you do?

Pitch digital marketing services to large companies, in person. I would resell more-reliable / higher-impact services than those provided by my current business partner.

What would a perfect day look like?

Waking up, going for a long walk or swim, meditating. Listening to a podcast or audiotape. Writing for 2-3 hours. Answering email, delegating tasks for the day. Getting lunch with friends or family. Reading for 2-3 hours. Going to the gym. Answering email. Getting dinner with friends or family or meeting up with an SO. Doing something fun and adventurous, preferably outside in nature.

What would make you most excited to wake up and do tomorrow?

An eagerness to express my ideas in writing and/or a compelling experience with people I love.

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Define the Key Role (If you name the role well, that’s almost half the work; try to get as detailed and specific as possible)

I am an entrepreneur and fitness athlete.

What would I do in the next twelve weeks if I had no momentum and couldn’t fail? (i.e. If you could start from scratch, what would you do? momentum matters, but only if it’s moving you in the right direction. To quote Peter Drucker, “There is nothing so useless as doing efficiently that which should not be done at all.”)

Move to the US, attend every conference possible, network like a madman. Start pitching the service to the right people.

Take stock—Where am I? (This is where you can start to incorporate momentum as well as figuring out where you need to course correct and what just needs to get flat out dropped.)

Where am I physically? In a city, about to attend a big networking event.

Where am I business-wise? Connected, somewhat. I have 3 mastermind groups and a private productivity group that, essentially, ensure that I don’t work as an island. However, to truly build my network I need to allow for serendipity. That means moving to a place where I’m regularly in contact with entrepreneurs, either by choice or by chance.

This summer was a summer of fun, but also a chance to meet many great entrepreneurs.

Moving to Saigon in 4 weeks will reignite the spark of networking-in-Asia. This year, I will stay in Asia longer than just 2-3 months. I plan to stay in Saigon for 2-3, then come back to Thailand for a month or two, then head back to Saigon for another 2-3 months.  I want to leave Asia in the Spring knowing being very secure financially and having the business on a clear growth trajectory.

What went well? What were three things I did right and should do more of?

Restarting productivity habit tracking. Getting back into the daily practice of tracking my habits in a Google sheet has been crucial to staying on track, keeping order amid the chaos, and seeing where I’m fucking up. Continuing this practice, making room for intuitive choices, and maintaining attendance and goals with my mastermind groups.

Connecting with other entrepreneurs and talking business. Listening to their issues in business.

What went badly? What were the biggest mistakes I made? Why didn’t I achieve what I set out to achieve?

One thing that must be improved is telling my story in business. Often times I find myself being unrealistically humble, and “listening” to other entrepreneurs out of misplaced deference. In reality, they (and I) would get much more value out of conversations about business when the conversation is a two-way street: both of us share problems, goals, what’s working and what isn’t’.

One of the biggest mistakes I made was partying too hard at one point in the summer. I did it despite the fact that it was going against my values. I ended up getting sick for more than a week after, lost a HUGE amount of momentum in business and in my social life, and also lost a fair amount of money. Looking back, I told myself not to do it, but did it anyway. The thing to remember is this: in the moment, it will seem like people will respect you less for making decisions based on your values (ie, sticking to your guns), but in reality the reverse is true. They will respect you more in the long run, not necessarily because they approve of your decision, but because, by reneging on your values, your self-esteem goes down and you’re less fun to be around. That is a very important lesson I learned this summer, and paid dearly for.

What are the three least valuable things I’m doing? What am I doing to avoid the Resistance?

This is a difficult question to answer. Many of my behaviors look valuable in a certain context. And the 4 big contexts I use to filter decisions are: health, wealth, happiness, and higher purpose. Everything I do moves me forward in ONE of those areas.

So, it’s easier to break down holes in my systems by looking at each area individually.

Health: the least valuable thing I’m doing is sacrificing sleep. Training 5-7 days a week requires, at the very least, 7.5 hours of sleep each night. 8.5 is ideal. So, any night that I get less than 7.5, my body aches, regresses even, and I’m not able to function well in business nor socially. One huge drawback of sleep deprivation – even a little bit – is that it massively blocks out the opportunity for serendipity, which, as I mentioned, is something I’m trying to optimize more for in the next 90 days. When I’m tired, my mind’s default mode is to block out stimuli, this causes me to miss a lot of opportunities that would have otherwise naturally presented themselves. Further, this constant “blocking-out” reinforces negative behavior patterns and ego defense mechanisms.

The Goal: Where do I want to be 12 weeks from now? If I am reading this 12 from today, what has to have happened for me to feel happy with my progress? (Here you’re trying to figure out what the right level of ambition for a goal is. Because ninety days seems to be the sweet spot in terms of estimating ambition and capacity, this is usually something that feels challenging, yet achievable. Once you figure out what that is, define criteria around it that will hold you accountable.)

Where do I really want to be in twelve weeks, but I’m too embarrassed to say it out loud?

Well well, maybe too embarrassed to say it out loud, but not to write it. Let’s look at two scenarios:

Scenario 1: Everything in my life is awesome: business, travel, money, success, fitness and physique. Except, my relationships are not where I want them to be.

Scenario 2: My relationships are all where I want them to be, but everything else in my life is severely lacking.

I would, without question, choose Scenario 2. This hypothetical tells me that building and managing powerful relationships – both personally and professionally – is extremely important to my happiness and well-being.

Although, I’m not sure this is an area of life that can just be fixed with a system, such as “call friends and family every day”. While that may work temporarily, I’ve tried it and it feels more like a band-aid solution. In relationships, identity-level change is what I’m after. Being a reliable, value-giving, fun, and generous man with everyone I meet is the ultimate goal.

Clearly Define a Goal and KPIs Maximum of 3 KPIs for each role, though one is best. These must be either a clearly defined, falsifiable result (e.g. Published a book, have 1k email subscribers)

Role: entrepreneur

KPI: 10 clients on monthly retainer

KPI: 10 email subscribers.

KPI: Hit $1000/month revenue from main authority site

Role: fitness athlete

KPI: maintain cut for 3 months, body fat <9%

KPI: Increase weight on all main lifts by 5% (OHP, Bench, Squat, Deadlift)

Role: ultimate man

KPI: the truth is, subjective well-being change should be obvious to me and to everyone around me. Ask friends and family, have I changed? How have I changed?

KPI: the quantity – but more importantly, the quality – of my relationships

KPI: the quality of the people I surround myself with. Do I have mentors and coaches?

The Why – Why do I want to be there? What’s the importance? (The goal isn’t important—it’s what it lets you do. The “why” is also what gets you to emotionally commit, so it has to be big, vibrant, and clear. I try to be completely honest with myself. If it’s a vanity-based thing that gets me excited, I’ll say that. Going through the “why” section will typically force me to go up and edit the goal if they don’t feel properly aligned.

Entrepreneur: Taking on clients gives me the opportunity to become better at what I do: better at business, productivity, and managing myself. A better networker, listener, and leader.

Both clients and a monthly revenue from my site give me the opportunity to have the freedom in my life to pursue bigger goals and chase my dreams: new cultures and languages, new heights and depths with fitness, better networking, more girls.

Having an email list allows me to share what I’ve learned with other people. It’s a way to find and connect with people who think like I do, and to learn from them.

Fitness: I’ve covered my reasons for going to the gym. It’s part of who I am. Even when I feel like shit, when I’m low on $$$, when I’m sick, when it’s HORRIBLY inconvenient, when there’s massive opportunities I’m missing out on, when the fucking sky is falling, I will still go to the gym and get my reps in. A little psycho? Yep. The main reasons: more health and energy, living longer, being a role model for friends and family, being someone who follows through, being someone who focuses on long-term results, better relationships, better sex.

Ultimate man:

This is simple: I want to feel like a loving person to the core. This means, having my behavior motivated from a place of love, not fear. Sounds woo-woo and esoteric, but it’s not. These decisions are always around us, happening in every moment. How do we act? I want to be someone who naturally behaves in a way that inspires others.

The How – How do I get there? Specifically: (This is where you’re bridging the gap and starting to get into what the details that really need to get taken care of are.)

What dangers do you have now that need to be eliminated?

Danger: drugs and alcohol. Plain and simple. Have always been a vice, and therefore will always be a temptation.

Danger: days off.

Danger: too much adherence to habit. It’s important to be flexible in the approach.

Danger: self-deceit. Easy to fool myself that I’m making progress towards goals if I’m working alone. I must submit my work, my ideas, and the results to the scrutiny of others. I must have skin in the game. Hiding = stagnation.

What opportunities need to be captured?

All of them. Opportunities are scarce. There is a heuristic for making decisions that goes like this: The answer is either hell yes or fuck no.

By definition, opportunities are always a HELL YES. What, specifically, are the opportunities that I’m looking for? Experiences that expand my general optionality; meeting more entrepreneurs, working with different kinds of businesses, working in different media.

What strengths need to be maximized?

My ability to communicate, personally and professionally. Personally, this means expressing strong boundaries and clearly stating what I want in a relationship.

Professionally, this means becoming a better writer, better speaker, and knowing specifically what the obstacles are in my business and how I’m working to overcome them.

What does the day-to-day life of someone that has already achieved this goal look like?

Reading, a lot. A person who’s achieved these goals is constantly reading and discussing ideas with others.

A person who’s achieved these goals is very clear about what they’re doing moment to moment. Days are parted in ways that allow for flow in each activity.

Playful. Someone who’s achieved these goals takes life seriously, but not himself. In everything he does, there is a sense of underlying joy and play. This applies to both work and relationships.

90 Day (Quarterly) Big Initiatives

Once I’ve gone through and done the review and started to break it down into a hot, I break it out into a document (usually a note in Evernote) that I can reference throughout the quarter for monthly and weekly planning to carry the “review” content into action steps.

The Role: Entrepreneur and Fitness Athlete

Why (copied from question 5 of the review):

Being a better entrepreneur opens my life in a number of ways:

Taking on clients gives me the opportunity to become better at what I do: better at business, productivity, and managing myself. A better networker, listener, and leader.

Both clients and a monthly revenue from my site give me the opportunity to have the freedom in my life to pursue bigger goals and chase my dreams: new cultures and languages, new heights and depths with fitness, better networking, more girls.

Having an email list allows me to share what I’ve learned with other people. It’s a way to find and connect with people who think like I do, and to learn from them.

How: (copied from question 6 and converted into phrases that start action verbs):

To create more optionality in my business, I must default to networking and connecting with other people who stimulate ideas. These people are equally driven and ambitious. They are entrepreneurs and creators. To accomplish this, I will regularly say HELL YES to opportunity, attend events, and live in proximity to other entrepreneurs and driven people.

Result/KPIs: (copied from question 4 and something I look at daily):

KPI: 10 clients on monthly retainer

KPI: 10 email subscribers.

KPI: Hit $1000/month revenue from main authority site

KPI: maintain cut for 3 months, body fat <9%

KPI: Increase weight on all main lifts by 5% (OHP, Bench, Squat, Deadlift)

KPI: the truth is, subjective well-being change should be obvious to me and to everyone around me. Ask friends and family, have I changed? How have I changed?

·KPI: the quantity – but more importantly, the quality – of my relationships

KPI: find a model/mentor for the areas of live where I have none (relationships and higher purpose)