How to Plan for First Time Success

One of the main tenets of the #365firstschallenge is to maximize your life through first times and new experiences. In a year where quarantine and lockdowns have altered how we operate, there’s still plenty of opportunity to cross off some of the firsts on your list!

In order to start planning for success, it’s important to be clear on your goals. Oxford Languages defines a goal as “the object of a person’s ambition or effort; an aim or desired result.”

A long-standing goal of mine is to learn Spanish. What I wouldn’t give to engage in conversations with people I meet on my travels! I have tried and failed in my attempts to learn the language over the years. Why? Lack of planning. I didn’t take into consideration the time commitment and over-extended myself in the process.

With this in mind, let’s get crystal clear on your goals and how to work toward achieving them.


List out the first times and new experiences that you’d like to accomplish. For inspiration, check your #365firstschallenge app and/or your Vision Board for first times or new experiences that you’ve been meaning to cross off your list.


If you’re like me, you’re eager to try new things and set a lot of goals for yourself. Consider what’s feasible given resources and constraints, such as time, seasonality, location, etc. Which first times or new experiences on your list appeal to you the most? Place a star next to three of them.


Now that you have identified three firsts to focus on, what are the steps you need to take to accomplish each goal? Breaking each item down to its component parts allows you to get a better sense of how long it might take to reach the finish line.

Some firsts may take much longer than others to complete. In cases like these, try to slice and dice your goal into a smaller one, and choose a more manageable first for the short-term.

For example, I would like to start learning Spanish again, but fluency in the language will take a while. After some slicing and dicing, the initial first time that I’d like to accomplish is to have the ability to comfortably make small talk. Breaking this down further, my journey to small talk contains the following: researching ways to learn the language (apps, live instruction, etc.), choosing how I’ll learn (and hiring an instructor, if applicable), setting a cadence for learning (one lesson per week), personal practice (15 minutes daily), and conversational practice (2 conversations per week).


Knowing what it will take to achieve each of your goals, you need to give yourself a deadline. Reflect on the entire ecosystem of your life and the free time you have available. What makes the most sense? Jot that down.


Using the deadline as a starting point, work backward to list out the steps in an orderly fashion. I recommend tracking and/or visualizing to stay on schedule. Some possibilities for tracking include a planner, app, or spreadsheet. Set up each day or week (whichever fits your method of tracking best!) so that you edge closer and closer toward your goal.


In times like these, it’s sometimes hard to stay focused. The squirrel mentality is real. So many issues and events are competing for our attention that it’s hard to stay on task. There is where leaning into accountability can be a tremendous help.

Accountability can mean different things to different people. This could look like sharing your goals with friends, family, or even your social network. For me, I find that virtual co-working is really helpful in keeping me on task.


And when you cross an item off your list, CELEBRATE! Be proud of yourself for trying something new. We can sometimes be guilty of minimizing our achievements, when in reality we should applaud the time and energy we put into doing something that excites us!

Your Turn

What are some first times or new experiences that you’ve been meaning to cross off your list? Do any of your goals seem especially daunting? Have you started and stopped pursuing any goals in the past? Head over to the #365FirstsChallenge Facebook group for accountability and support in the pursuit of your next first time or new experience!

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