Over the last several years, I have focused on creating structured processes for teams and companies to develop strategy, establish goals, and execute on those goals. I have lead strategy offsites, driven OKR setting and scoring, and developed frameworks to guide resource allocation to top priorities. A few years ago, I decided to apply my learnings to my own life and set up an annual ritual I call Personal Offsite.
What it is:
A personal offsite is a ~24 hour journey I take every year somewhere away from home to reflect on the year that just passed and to set goals for the upcoming year. I also take the time to evaluate if my longer term goals are still relevant and on track.
Why I do it:
I started doing this when I was moving from one job, in which I spent six years, to another. I had the idea of driving somewhere from my home in San Francisco until I ran out of gas and then finding some place to spend the night to reflect on my life. The whole experience was meant to be a time for me to reflect on what I ultimately want to accomplish on many dimensions of my life, including professional, personal, family, etc. I organized and was part of many strategy setting offsites in my professional life, so I thought why wouldn’t I do the same for myself.
As I sat in a coffee shop in San Luis Abispo, deep in reflection, I realized that I should have probably done an offsite like this before I made the decision to change jobs, not after. It may have not changed my decision but it would certainly have helped provide better context for me to think through the decision. That insight led me to turn this personal offsite into a regular annual ritual. Having done it now three times more, I really find value in taking this time to reflect deeply away from the day-to-day to-do lists and the familiar environment of my home and city. I now use it to evaluate the wins and misses of the year that passed and set goals for the upcoming year – in a way, this is my new year resolution setting time but it’s a bit more involved than setting a weight loss target.
What does it practically look like – the mechanics:
The prep:
I really take very little time to prep. The main elements of preparation for me are
a) arranging with my wife the date when it will be convenient for me to disappear and leave her with our two kids,
b) picking and downloading a book for the journey there, and
c) picking a destination (usually a place where I’ve never been before or never stayed overnight that’s at least an hour away from my home),
d) booking a hotel for the night.
The journey there:
The journey is an important part of the experience. I like to use it as a) a separation from my routine, and b) to get excited for what I am about to do with some new book. I typically download a book on Audible and listen to it on the way to my destination (previous books included: Awaken the Giant Within by Tony Robbins, Your Best Year Ever by Michael Hyatt). I usually finish the book either on the road or subsequently in the hotel.
The two pronged experience:
- Leisure: My Personal Offsites started after I was married and had kids. For those not yet at that stage in life, being married with kids tends to mean that I don’t have much “me” time. So I use the Offsite as a way for me to treat myself. I typically leave my home before dinner so once I get to my destination and check into my hotel, I find a nice restaurant (typically sushi) and go sit at a bar, have a nice feast and finish listening to the book from the journey, if I haven’t already. It is important to note that this experience of eating by yourself may feel awkward at first. The whole experience is a bit of an introvert heaven, but I truly don’t think only introverts can benefit from this. If you are a good, smart, interesting person, you can enjoy your own company for a few hours – it won’t kill you. Introverts and extroverts alike probably don’t do this kind of introspection enough. Back to my dinner…, once I am done with my feast, I head back to the hotel and after doing a bit of planning for next day, I turn in relatively early and set my timer (not alarm) to 8.5 hours. For me, this is an important luxury that is roughly 50% greater than my average day. In the morning, I like to take the time to pamper myself. As an example, on my 2018 Offsite in Santa Cruz, I started with a trip to the treadmill, then some sauna, then jacuzzi, then the pool, back to the sauna, and then shower. I then treat myself with my favorite breakfast, which is lox bagel sandwich and coffee. Then it’s time to do some planning.
- Planning/reflection: Once I find a good coffee shop (e.g. Verve in Santa Cruz), I spend the afternoon on my iPad in a google doc, reviewing my goals from last year, jotting down wins and misses, and setting goals for the year ahead. It’s important for me to have long term goals (Someday & Five Year goals) that I set up some time ago and that I revisit annually, but I spend the bulk of my time seeing what I need to do next year around the various aspects of my life to have a successful year and to make sure they are aligned to my longer term plans. There are books written on goal setting, so I won’t go into depth here, but I like to have SMART goals (Specific, Measurable, Achievable, Relevant, Time-bound) around areas that are important to me: Personal (physical health, hobbies, intellectual), Family (wife, kids, parents/siblings), Financial, Professional, Community (charity). It’s very important to not just write down the specific goals, but to also articulate reasons why those goals are important and to develop an action plan. Also, an interesting technique I recently developed around goals is to hide affirmations in a password for something I use daily (e.g. your computer). For example, imagine how powerful it could be to have to type in “I_will_have_a_million_bucks” every day. Try it! Affirmations can be powerful in helping achieve our goals. I like to leave the offsite having set some recurring calendar invites on my calendar (e.g. finish my monthly book). When I am ending my offsite, I tend to pick out one of the goals that is most important to me. Usually it’s about getting to sleep earlier, since that’s a big missing piece in my life; succeeding here helps me achieve many of my other goals (yes, sleep is that important). When I get home from the offsite, I share the goals with my wife and ask her to commit with me to those things where I need her help to succeed. This step is very important if you have dependencies in your goals.
Conclusion:
I put this simple ritual down on paper because every time I mentioned my personal offsite to someone, people got excited and later told me they went ahead and did one of their own. The reality is that we are running around from one task to another, from one screen to the next, and we don’t take time to think and evaluate our lives. Before you know it, your career, family life, etc. evolved on their own and you may not like the current destination. This is a small but meaningful tool to put you in the driver’s seat of your life. Sounds corny, but it’s amazing how much more in control I feel every time I spend these 24 hours on my Personal Offsite.
A Guide to Personal Finance for My Kids or Yours 