• A step-by-step approach to setting and accomplishing goals in the most important areas of your life
  • A proven system for staying on track
  • First-hand account from someone (me!) that spent two years being my own test dummy
This is the first post of a three part series. 

“I’ve tried setting goals, but I never see them through. I lose motivation easily.”

“There’s so many thing I want in life (better job, start a business, etc.). Where do I even start?”

“I want to eat healthier and exercise more (or insert any other habit), but those habits never stick.”

Any of those ring a bell? These were the excuses for why my New Year’s Resolutions in 2012, 2013 and 2014 didn’t work out.

Statistically, 80% of New Year’s resolutions fail by February [1]. I guess I’m not alone!

I didn’t start taking goals seriously until the end of 2014. I was 25 years old, had just left a year and a half long relationship, and failed my first attempt at being an entrepreneur. Oh, and I had about $30,000 worth of credit card debt.

After feeling sad/depressed/lonely/hopeless for about six months, I decided that 2015 would be my year.

I was very motivated to create massive change in my life. It was November of 2014, so setting a few radical New Year’s resolutions sounded like a good thing to do.

The only problem? I didn’t follow through with the previous three years of New Year’s resolutions.

I didn’t know how to set really set goals or, most importantly, how to stay on track and actually accomplish them.

Goals had always been set for me up to that point in my life. I had quotas and revenue targets in my previous jobs, which my employers set for me.

How This System Has Helped Me

I spent the next two months studying as many articles, books and podcasts I could find on how to properly set goals. I also interviewed guests on the GenY Success Show and picked their brain on successful systems they use to set and track their goals.

The rest of 2015 and 2016 was spent refining the system I’m going to share with you in this 3-part series of posts. My goal is that it doesn’t take you two years to find a system that works for you!

Here’s how this system has helped me:

  • Paid off $30,000 worth of credit card debt (took 2 years)
  • Started five business (two of which have failed)
  • Made a six-figure+ income as an entrepreneur and freelancer
  • Started my first podcast
  • Took four improv classes
  • Started doing stand up comedy
  • Built and continue to build relationships with mentors and other successful peers

These things are all very important to me, but they may not be important to you. My goal is to help you find out what’s most important to you.

This Post Is Not For You If…

Reading this article will not help you “manifest your destiny.”

Finding your “destiny” is woo woo bullshit I don’t believe in. If you’re not willing to work your ass off for the lifestyle you want, stop reading right now.

Ok now that I got that out of the way, let’s get to the good stuff!

Start With What’s Important

What do you value? Your values became the framework for setting meaningful goals, and act as a filter for new opportunities.

I’ve set too many goals that “sound cool.” Or that look cool to share on social media. Fuck that noise. I want you to focus on what’s important to YOU. Not your mommy or daddy, not your high school friends on Facebook, and certainly not the haters in your life.

Let’s get started by asking yourself a few questions.

1. Think back to a time when you felt extremely happy…the happiest you’ve ever been. What moment(s) in life comes to mind? What did you value most about those moments?

Jason Bay Basketball - GenY Success
High School, Senior Year 2007. With Coach Wood right after we secured a spot in the State Playoffs.

On my high school basketball team, we had an award called the “Bruin Award.” It was given to the student on the team who demonstrated best what it meant to be a great student, person and athlete. One of the happiest moments in my life was when my high school basketball coach told me he was going to rename the award to the “Jason Bay Award.”

What I valued most from this was that, besides my dad, my basketball coach was one of the few people who recognized who I was as a person BEFORE who I was as an athlete.

Reflecting on this moment has helped me realize that I value mentorship and relationships with people who care about integrity and being the best person you can possibly be.

Another moment that comes to mind was leaving my job to start my first business. I quit my job as a Marketing Director and went straight to sleeping on my business partner’s apartment floor for the next two months. The business ended up failing after six months, but I took the leap.

This experience taught me that I value freedom. The constraints of a 9-5 limit my earning potential, ability to take time off, and to do the work I love.

I also value personal growth and taking risks. I need to lean into what scares me. Be bold. Take risks.

2. Now think back to a time when you felt extremely unhappy. What moment(s) comes to mind? What did learn from those moments?

Right after college in late 2011, I moved down to Orange County, California to become the Marketing Director for the company I worked for throughout college, College Works Painting.

I always wanted to live in a big city. Who doesn’t dream of living in Southern California at some point in their life?!

I spent close to three years down there and the last half didn’t go so well. I had trouble making friends, and didn’t relate well with the people down there. Orange County has a very materialistic culture, which I don’t value. It’s neither good nor bad. Just wasn’t for me.

I racked up around $30k worth of credit card debt during this time buying stuff I didn’t even value. My friends didn’t really care about personal growth and development. I lived for happy hours and weekends. Finding a like-minded girlfriend was also though. I was really lonely.

What this experience taught me is that I don’t need to live in a big city to be happy. I don’t care about the brand of my clothes. Surrounding myself with people who care about personal growth is important to me.

Here’s a quick recap:

  • I value mentorship
  • I value personal growth and calculated risk taking
  • I value close personal relationships with people who value personal growth and integrity
  • I value freedom in my work

These four values are the framework I use to set my goals.

Take the time to figure these out before you move to this next section.

If you’re struggling, listen to this interview with Jess Lively. Jess and I discuss values-based goal setting. She suggests using this guide to determine if your values are meaningful or not:

  • Present moment. Can you embody this value right now in this moment?
  • Peaceful. Does living this value make you feel peaceful, regardless of the outcome?
  • Positive. Is the value stated in the positive?
  • Flexible. Can you live up to this value no matter the circumstance?
  • Fulfilling (Innately). Is this a value you expect of yourself? And not what others expect of you?
  • Enduring. Can you live this value for the rest of your life?

If you’re still struggling, post a comment below and I’ll do my best to help you out.

How To Set Goals

I’m not a “hippie dippie” person (The Secret is the WORST MOVIE AND BOOK EVER). However, a solid set of 3-5 values you stand by is extremely important. Your personal values act as your filter for new opportunities and deciding who you want to surround yourself with.

This next section breaks down the mechanics of setting solid goals.

Milestones Vs. Habits

Habits are the consistent actions that help us to achieve our goals. Milestones are the results we are hoping to achieve. Habits are typically measured by effort (did you or did you not work out today?) and milestones are measured by results (did you lose 15 pounds?).

It’s important to distinguish between these two.

For example, let’s say your goal is to lose 15 pounds in the next 90 days. Your milestone is exactly that: lose 15 pounds in 90 days. You can clearly measure the results.

The habits required in order to hit that milestone are more action-oriented: exercise three times per week, adopt a Paleo diet, limit sugar, weigh yourself each morning, etc.

James Clear believes that if you focus on the right habits (he calls them “systems”), the results will likely take care of themselves [2]. I agree.

In the example above, building consistent habits will help you hit your weight-loss goal AND keep the weight off.

When setting goals, identify the result you are intending to accomplish (the milestone) and identify the reoccurring actions (the habits) that will help you hit that milestone.

Your ability to incorporate consistent habits into your daily and weekly life will have a direct correlation in your ability to accomplish your goals.

Start With the M.A.P. System

I’ve read dozens of articles on SMART goals. I don’t hate the system, it’s just a little ambiguous. No one seems to agree on what the acronym stands for [3] [4] [5] [6] [7].

  • S – Specific
  • M – Measurable
  • A – Actionable or Achievable or Attainable
  • R – Realistic or Relevant or Responsible
  • T – Timely or Time-Oriented or Time-Bound

WTF?! How about this instead…

You’re at Point A right now, and you want to get to Point B. If you were in Portland, Oregon and you wanted to drive to Los Angeles, California, you probably wouldn’t just start driving south towards California and hope for the best.

I’m sure you’d use a map. Think of your goals as just that: a road map.

So let’s just use M.A.P. as the acronym. I know, I’m so creative.

  • Measurable. Can you clearly define measurable actions and results to know whether you succeeded or failed? Have you established a deadline to measure against? If you can answer “yes” to both of those questions, your goal is measurable.
  • Actionable. Is this something you could start taking action on RIGHT NOW? If you can’t identify the action you must take, then your goal is not actionable.
  • Personal. Is this goal personal to you? Do you CARE about this goal? If you set goals based on what you “think” other people or society wants you to do, then your goal is not personal.

Doesn’t need to be more complicated than that.

What does “realistic” or “achievable” even mean? When Steve Jobs set out to put a personal computer in the every day consumer’s hands, I doubt he was thinking about how “realistic” it would be. Everybody was telling him he was crazy, but that didn’t stop him.

Set Goals In These Three Categories

Now comes the fun part! If you’ve never set goals before, don’t stress. Just think about what you want in the next 90 days. If you’re fairly experienced with this, try 1-3 years.

I don’t focus on much more than a year at a time at this point in my life.

This is just a brainstorming exercise to find what’s most important to you. The next post will explain how to prioritize your goals. If you came up with a list of 30+ goals that wouldn’t be a bad thing! And if it was just a few things in each of these areas, that wouldn’t be bad either.

Focus on setting goals in these three areas:

#1: Personal. Focus on areas like your relationships, personal habits, possessions, or personal development. Here are a few examples:

  • Finding someone to be in a long-term, committed relationship with
  • Strengthening your current relationship by spending ______ more time together
  • Strengthening the relationship with your parents by visiting them ________ times per year
  • Improving your dental hygiene (flossing, using mouthwash, etc.)
  • Losing _________ weight
  • Getting in better shape
  • Eating healthier
  • Reading _______ books this year

#2: Career. Focus on what you do for a living. You could be running a business, working a job, or both. Here are a few examples:

  • Make _______ amount of income
  • Find a job I love
  • Start my first business
  • Grow my current business to _________ revenue
  • Write a book
  • Start a blog
  • Start a podcast

#3: Fun. The most neglected area of them all. Goals create our lifestyle, which is what we live with on a daily basis. Don’t forget to have fun along with the way. Here are a few examples:

  • Taking a stand up comedy class
  • Taking an improv class
  • Taking an acting class
  • Traveling, taking vacations
  • Anything else you have on your bucket list

Having Trouble?

If you’re struggling to find out what’s important to you, don’t worry. It’s normal!

It’s something many of us struggle with. Here are a few questions to help you:

  • What do I enjoy doing? You don’t need huge goals like Elon Musk. They can be as simple as, reading my favorite fiction books for 30 minutes / day. Or saying “I love you” to your partner every day. Anything you enjoy doing can be a goal.
  • What would I be doing right now if I had $10 million sitting in the bank? If you could make a living doing what you wanted, instead of what you had to do, what would you be doing?
  • What have you felt a tremendous amount of resistance towards trying? What have you been procrastinating? Writing a book? Starting a blog? Lean into whatever that thing is.
  • What’s on your bucket list? What have you always wanted to do?
  • How did the last 12 months go? Reflect on what made you the happiest, and also the most stressed. Set goals to do more of what makes you happy and less of what doesn’t.

Take Action

Come up with your list! Remember, the goal is to come up with as many goals as possible. It could be 30+, or it could be 5.

Try not to spend more than an hour or two on this exercise.

The next post will focus on how to prioritize this list to find out what’s most important to you.

Where are you struggling? I’d love to hear about it in the comments below.

Click here for part 2 of this 3-part series.



  1. http://www.businessinsider.com/new-years-resolutions-courses-2016-12
  2. http://jamesclear.com/goals-systems
  3. health.mo.gov/living/families/wic/wicupdates/doc/GoalSetting-SMART.doc
  4. http://hr.wayne.edu/leads/phase1/smart-objectives.php
  5. https://en.wikipedia.org/wiki/SMART_criteria
  6. http://topachievement.com/smart.html
  7. http://topachievement.com/smart.html
  8. https://www.mindtools.com/pages/article/smart-goals.htm