And now for a blog post on my favorite topic: goal-setting!!

I may be a little obsessed with setting goals. In December, I read my journal and assess how I tracked against my annual goals and then determine what goals I want to set in order to continue growing and challenging myself for the upcoming year. I have a white-board in my apartment with all of my goals and a 2-month calendar view that is color coordinated against my goal buckets.

One of my goals for 2019 is to teach a workshop, and with the year coming to a close very soon, I’ve decided to offer a complimentary workshop in Midtown NYC on Sunday December 15th from 11am - 12:30pm to help you set your 2020 goals. You can sign up here if you are interested.

Goal Buckets

The purpose of goal-setting is to create a life that you’re excited about and that is authentically you.

There is a crazy societal belief that people can find one thing they are passionate about and it can drive all of their life decisions and infuse every moment with meaning and enjoyment. Unfortunately, no one thing can provide this to us. Therefore, when you are setting goals, you have to look at all life categories. I find Bill Burnett’s and Dave Evan’s framework from Designing Your Life to be most helpful in thinking about all aspects of your life. Their framework focuses on four life buckets: work, health, play and love.

How do you feel right now?

Before we jump into goal setting, take a look at the 4 goal buckets. What activities can you include under each bucket? How do you feel about your activities in each of the buckets?

Maybe you’re doing a great job at work, but at the expense of connecting with friends. Maybe your outside work life is thriving, but sitting in the office everyday makes you miserable. Maybe you are crushing it at work, with your friends and at the gym, but you feel burnt out and need to incorporate more play time into your day-to-day. It’s important to always check in with yourself and see if you are consistently neglecting a certain life bucket. If so, this neglected bucket could be the focus of your goals.

Now that we’ve checked in with ourselves on the current state of our world, let’s discuss a few guidelines on where you should focus your goals.

I’ve deemed “should” one of the worst words in the English language. I find that my “shoulds” are marked by expectations from others, rather than a reflection of my true desires.. Even if these “shoulds” are in conflict with what we truly want, we tend to hold onto them because they are familiar and provide a sense of comfort. We are also fearful that the outcome of change will taint us (e.g., leaving finance will make me unsuccessful; breaking up with my partner will mean that I am alone forever, trying out a new hobby will make me look stupid).

When I was at my old job, I was unhappy and not performing well. I kept telling myself - “the next project will be better, I’ll be on a better team, the content will me more interesting and I’ll have a better attitude about work and I’ll like my job.” Even though I was unhappy at my job, I almost turned down a job offer I received because I thought about losing the prestige of consulting, the positive relationships I had developed at the firm and how the next job could be worse. Luckily, my family and friends convinced me to take the job and I am so much happier now because I’m in an environment that more aligns with what I truly want.

In what areas do you feel the tension between what you “should” do and what you “want” to do? Are you willing to leave the “shoulds” behind in 2020?

As we learned in Blog Post #4, humans are terrible at predicting what we want and how we are going to feel in the future. Therefore, it is important to put ourselves in situations where we can test our “wants” and make sure we truly want them. The process of testing new ideas or hypotheses - prototyping - prevents us from devoting significant resources, time and emotional energy to a goal that we are not actually excited about, even though we thought we’d be.

For example, in between jobs, I prototyped career coaching – I thought career coaching was what I wanted to do with the rest of my career. After 2 months of career coaching, I realized I never want to do it again, let alone make it my job. Even though I expected to love career coaching because I enjoy working with people and helping them brand themselves to achieve their goals, the day-to-day work focused on updating people’s resume became very unchallenging and transactional, and hence, demotivating.

Before setting arduous goals, it’s important to engage the prototyping mindset. I see so many people commit to finding a job in a certain field, without ever really questioning if this is truly what they want. They spend hours applying online to jobs, networking with people in the industry and reading interview prep guides. When they finally get the job, they realize it’s not what they wanted. Conversely, if you engage a prototyping mindset, you can say - “I think I want to go into the tech industry.” You can set up informational interviews with 5 people in tech and see if their day-to-day sounds like something you would enjoy. If after 5 informational interviews, you’re still very excited about tech - then march forward. But if not, now you have more information on what you are and are not looking for in a role and can pivot your job search accordingly. You’ve saved yourself hours of prep in the wrong area in the meantime.

Overall, when you’re in the early stages of figuring out what you want, it’s important to prototype before setting an arduous goal.

What are you going to prototype in 2020?

In 11th grade, I decided I wanted to go to UPenn, based on visiting the school, talking to the admissions counsel, talking with friends and evaluating colleges against my personalized criteria. My parents told me that it was very unlikely that I was going to get in because half of the students in my town were Penn legacy and I didn’t have this status. Like all teenagers do, I ignored my parents advice and applied early to Penn. Luckily, the stars aligned and I got in! After doing much research, I took a big calculated bet, which has impacted by job opportunities, friends and perspectives going forward.

You can take a big calculated bet and it cannot work out as intended, but nonetheless, I always find that I learn so much about myself in the process. After spending significant time with a guy friend, I realized I had romantic feelings for him. I knew that our friendship would suffer if he did not reciprocate these feelings, but it was a bet I was willing to take after spending lots of time together. He did not reciprocate these feelings, and while this hurt in the short-term, I’ve learned so much about myself in terms of how I manage rejection and conflict and what I prioritize in relationships.

No matter what the outcome, I am a fan of big, calculated bets that are backed by prototyping. Change and progress starts with small steps, but eventually you have to make the jump to propel change forward.

What big calculated bets do you want to take in 2020? Is there any additional prototyping you need to do in order to make sure you’re ready to make a big calculated bet?

Okay, so now we’ve reviewed the guidelines for where you should focus your goals, let’s review how to actually set goals

When setting goals, people tend to focus on outcomes, rather than the process - this is not an effective approach. Outcomes are often influenced by factors outside of our control - promotions (hello office politics) or finding a significant other (you cannot control what other people do). Process-based goals (e.g., making 10 cold calls a day for new sales) will enable you to stay committed to your goals because effort will directly translate into positive progress.

It’s impossible to pursue all of your goals at the same time. I like to have 2-3 month sprints focused on 2-3 goals. For example, in January and February, my focus was (i) working out, (ii) prototyping a bachelorette planning start-up and (iii) dating because work was less intense. In March - May, work was much busier and my priorities were (i) work (ii) sleep and (iii) working out. By having this goal sprint approach, it allows you to work on cultivating the life you want, while taking into account environmental factors and time limitations.

In summary, setting goals helps direct us towards changes that support the creation of a more authentic life. I recommend taking some time over the next 2 months to reflect on what type of life YOU want and setting priorities for 2020 that help get you closer to it.