6 Lessons Learned Setting and Achieving Goals

Photo by S O C I A L . C U T on Unsplash

While in self isolation, many of us  are trying to take advantage of our time to set goals and build new habits. As humans, however, we struggle because let’s be real, change is freakin’ hard! It’s difficult to stay motivated and focused when there’s so much uncertainty. Some days it feels like all you can do is just sit there staring out the window wondering, what’s the point?

But it’s important to remember that this is only temporary. We can either waste the  time we have watching the whole Tiger King series over and over again (I’ve already watched it twice), or we can make the most out of our time and invest in ourselves. We can use this time to build new habits that get us closer to achieving our goals and work towards feeling a stronger sense of accomplishment and purpose in our lives amidst all the chaos.

A week ago a friend of mine, Jillian Alyse, sent me a direct message on Instagram and asked if I’d be interested in doing a live Q&A about setting and tracking goals. I was excited by the idea so I agreed.

During the Instagram Live Q&A, Jill asked me questions such as:

  • How do you get better at setting goals?
  • Why kind of questions do you ask yourself when setting goals?
  • How do you stay motivated and on track?
  • How do you motivate yourself when you really don’t feel like it?

The feedback was very positive. Both Jill and I had friends reach out to us afterwards to thank us and share how it helped motivate them with their goals. We also got a few follow-up questions.

I’m all about sharing and repetition, so figured it may be helpful to those  who couldn’t attend to get the same tips here. Here’s a summary: 

I’ve been a very goal-oriented person for as long as I can remember and continue to set goals both personally and professionally. This goal-oriented mindset has helped me advance in my career quickly and has given me more confidence and a feeling of purpose in my life. But while goal-setting came naturally to me, actually achieving my goals wasn’t as easy. I’ve set goals and forgotten about them only to be reminded at the end of the year that I did nothing to push them forward. They were either unrealistic or I simply wasn’t passionate about them and therefore gave up quickly. I beat myself up for abandoning the goals I set for myself. There are a lot of mistakes I’ve made, but each time I’ve learned how to get better – both at setting and achieving goals. I’m only human so of course there are things I still struggle with everyday, but overall I’ve gotten much better through experimentation and deliberate effort.

Lessons learned setting and reaching goals

Lesson 1: Ask yourself your WHY

In the past, I’ve set goals that were influenced by other people or that seemed like things I should do. For example, I once set a goal of wanting to deadlift almost twice my bodyweight. Why? Because I saw another girl post on Instagram how much she could deadlift and I thought to myself, “I want to be able to do that.” A few months later I felt I wasn’t making enough progress and just wanted to give up. I felt defeated and shitty. The problem wasn’t the fact that I didn’t achieve the goal or the goal itself. The problem was that I set that goal for the wrong reasons. I set a frivolous goal because I was comparing myself to someone else, not because of something I truly wanted to achieve. Setting arbitrary goals on a whim or influenced by someone else just ends up making you feel shitty about yourself when you don’t achieve them because you’re not actually committed enough to put in the work needed.

Now when I’m thinking about a new goal, I ask myself a series of questions before committing to it. This helps me clarify my goal and make sure it’s something I’m serious about and willing to put the work into. One of the questions I ask myself is why?

By thinking over the purpose, reason, or benefit of pursuing a goal, it helps me be honest with myself about whether or not it’s something I should commit to. If I don’t have a strong why, I erase it from my list and focus my energy on other goals that I’m actually passionate about and willing to put the effort into.

Lesson 2: Ask yourself what you’re willing to sacrifice

Another question I ask myself before committing to a goal is, what am I willing to sacrifice? I’ll try to conduct a cost benefit analysis; thinking through what’s involved in achieving it. For example, last year I set a goal to touch my toe to my head in a dancer pose and I gave myself a year to do it. Why? Because I wanted to work on my flexibility and knew this was a way to challenge myself to keep working on it. At the time I could barely balance on one foot for more than a few seconds and I was at least 2 feet away from being able to reach my toe to the back of my head.

I thought about what it would take to achieve this goal. I did some research on stretches to practice leading up to this pose. I could barely do any of those “beginner” poses. I knew trying to reach this goal would mean I’d not only have to practice stretching almost every day, it also meant I’d have to sacrifice some of my weight lifting time to do this in the morning. It also meant I’d have to struggle through painful stretches that would likely result in me falling over more often than not, months of failed attempts at poses that were difficult, and potentially some pulled muscles. I decided I was willing to make that sacrifice. A year later and I got about an inch away from touching my toe to my head. I didn’t officially reach my goal, but I was impressed with the progress I made and it’s become an ongoing practice.

January 2019 VS December 2019

All goals require sacrifice. It’s better to be honest and upfront with yourself about whether or not you’re willing to make the sacrifice before you start pursuing it.. But if you think through the pain and sacrifice involved in pursuing a goal, and you’re still willing to do it, then you know you have a high probability of reaching it because you’re willing to make the necessary trade-offs.

Commit to a goal or scratch a goal off your list, but do it deliberately.

Lesson 3: Share your goals with your support system

Trying to build new habits and reach new goals is challenging. It involves failing multiple times as you figure out what works and what doesn’t work. To increase your odds of success, share your goal with your support system once you’ve committed to it.

Having a strong support system is so important because at some point or another you’re going to feel like a failure, feel defeated, and be tempted to give up. It’s easy to get stuck in your head and listen to your self sabotaging thoughts. Having a friend or family member that you trust can help build you up and give you the encouragement you need to keep going.

Each year I set a goal for myself that I know will be extremely challenging and will take me the whole year to achieve. For 2020, I set a goal of writing a book. I gave myself the last month of 2019 to write an outline and at the start of 2020 I began writing my first draft. A few months in and I started to question myself. Do I even know enough to write a book? Even if I get it published, who’s going to read this book anyway? I’m a nobody.

Anytime I got stuck in one of these self sabotaging thoughts, I’d confide with my close friends. They’d give me the confidence boost and kick in the ass I needed. They’d remind me of the purpose and impact of the goal. 

Everybody feels like a failure at one point or another. Talking about this with others helps lighten the load and give you newfound motivation to keep going. Talk about your goals and your struggles with the people that you know you can trust for honest advice, that care about you and want to see you succeed. They’ll help you shake the self sabotaging thinking and get back on track when you need it. But it’s on you to talk about it and be open.

Lesson 4: Motivation fades, it’s all about building discipline

Motivation is fleeting, self discipline helps you build consistency. One of the things people often say to me is, “Kris, you’re so motivated at reaching your goals!” The truth is I’m not. I’m actually quite lazy and unmotivated most days. I’m just disciplined as fuck. A majority of the time when I wake up in the morning I’m motivated to go back to sleep. I don’t feel like working out, I’m tired, and I often run through a mental list of excuses. What gets me out of bed to go to the gym is self discipline.

If you’re serious about a goal, you have to get over the idea that in order to achieve it, you need an unlimited supply of motivation. Be honest with yourself and know that self discipline is what you need to work on building. You have to push yourself to do things even when you don’t feel like it. You have to push yourself to keep trying even when you fail. And you do that by repetition. You start small and keep building. If you fail or fall off track, you pick yourself up and keep going even if you don’t feel like it. Do this one step at a time across multiple areas of your life, and building self discipline will start becoming second nature. The result is becoming unstoppable at reaching your goals.

Now that you know you need to build self discipline, the million dollar question is how? A simple two ingredient formula is structure + routine = self discipline. You have to create this structure and routine for yourself. For example, deciding what time you want to go to bed and wake up at then holding yourself accountable to sticking to those times. Deciding what days you’ll work out, then making yourself do it whether you feel like it or not. You have to give yourself the same tough love a strict parent gives their child, but you have to do that for yourself. It’s not easy, but if you keep working at it you’ll build this muscle over time.

I’ve built self discipline over decades of pushing myself to do things that I didn’t feel like doing. This includes waking up at 5:30am when it’s still dark out and too early to be alive or going to bed at 10pm even though there was a show on that I really wanted to finish watching. The more things you push yourself to do, the more disciplined you become. Once you prove to yourself that you can do it, you build your confidence and know that you can continue pushing yourself time and time again. You may fail a bunch of times, but you have to get over that. Failure is part of the process. On days I’m feeling extremely unmotivated, I remind myself that I’ve experienced this before. There’s been many days where I felt just as lazy and tired, but made myself workout anyways. I felt better afterwards and always thank myself later.  

Once you let go of the idea that achieving your goals is a product of motivation and accept that it takes self discipline (which eventually turn into habits), you can begin your journey to being disciplined as fuck and start smashing your goals. Part of this is building systems and structure that makes things easier on yourself so you don’t have to rely on motivation. I often read books about building habits which I then use to  experiment with various techniques to make it easier to reach my goals. 

Lesson 5: Write down your goals down & decide when and where you’ll do them

I used to write down goals on a piece of paper or in my journal and then never look at them again. As you’d imagine, I never achieved those goals. However, once I started writing down my goals and reading them over everyday, I drastically increased my success track record. Another key is to write down when and where you’ll take the necessary steps to reach your goal. 

For example, one of my goals is to workout 5-6 days a week. If I just set that goal, but don’t decide on which days of the week and what time of the day I’ll workout, then I’m relying on whenever I feel motivated to do it. And guess what, it’s not going to happen. It’s extremely unlikely that I’ll have 5-6 spurts of motivation during the week equally spread out and at a time that I’m able to do a workout. The reality is that in the morning there may be one day out of the week that I’ll actually feel motivated to get up and workout. There’s a very low chance I’ll feel motivated to workout after a long day of work and there’s about a 50% chance I’ll feel motivated on the weekend to workout. So if I rely on “whenever I feel motivated” to workout, it’s very unlikely that will happen and I’m inevitably setting myself up for failure.

So what I do instead is I write out a plan for which days of the week and what time of day I’ll work out. After workI feel tired and lazy. I’m more of a morning person so even though I’m tired in the morning, it’s the least shitty option for me. I also know that Saturdays I like to have a few drinks, which means Sundays I’m often a tad hungover and unlikely to workout. So I write my plan to workout in the morning Monday-Saturday. I stick to a routine and wake up at the same time and start my workout at the same time. Sticking to a routine makes it easier because I don’t have to rely on motivation in that moment. I just rely on my self discipline to get my ass up and do it. It’s easier when the decision is made ahead of time.

Pro tip: if you’re laying on the couch or in bed thinking about the thing you should be doing but you’re really struggling to do it, countdown from 5. Don’t think, just count down and then jump out of bed or off the couch like a rocket ship and do it. I learned this tip from Mel Robbins.

Lesson 6: Get an Accountability Partner

The secret sauce of staying on track with your goals is having an Accountability Partner. Even if you’re a disciplined person, sometimes your inner saboteur can get the best of you. When you have someone else holding you accountable, it increases your odds of success.

My best friend, Emily Rudow, and I have been friends since grade 3 and are both quite goal-oriented. When we lived together after graduating college, we were gym buddies, talked about our goals, and helped support each other.

So when I read about the idea of having an Accountability Partner, she was the first person that came to mind. About two years ago I asked her if she wanted to be Accountability Partners and she was down for the idea. At first we agreed to do a monthly check-in. At the start of each month we’d email each other our goals and then at the end of the month we’d review each other’s list of goals and ask how we did.

It helped, but I knew that doing a check-in only once a month was not enough. We needed to kick it up a notch. So we started doing a check-in once a week. At first we agreed to do this but didn’t decide on who would check-in with whom or what day/time to do the check-in. That was a fail. Within a week or two I suggested that I would text her every Monday at 11am. That worked better than the monthly check-in, but some weeks I’d forget to text her.

When I set my goal for the year of writing a book, I knew it would be challenging and I’d need even more support. I asked Emily if she was willing to take our Accountability Partnership to the next level and do a daily check-in. She was onboard. I told her I’d text her everyday by 8am with whether or not I accomplished my goals for that day and if she didn’t hear from me by 8pm, I needed her to text me back. She agreed and we gave it a go.

At the start of each week, we’d email or text each other our list of goals for the week.

My list of goals usually looked like this:

  • Workout 5-6 days for 20-30 mins per day
  • Do yoga 5-6 days for 15-30 mins per day
  • Meditate 7 days 10-15 mins per day
  • Journal 7 days at least 1 page per day
  • Write 1 blog draft
  • Work on my book at least 1 day
  • Read at least one evening after work

I’d then write out my plan for when and what time

For example,

  • Monday: Gym 7am, Yoga 7:30am, Meditate 8am, Journal 8:15am
  • Tuesday: Gym 7am, Yoga 7:30am, Meditate 8am, Journal 8:15am, Read 7pm
  • Wednesday: Gym 7am, Yoga 7:30am, Meditate 8am, Journal 8:15am
  • Thursday: Gym 7am, Yoga 7:30am, Meditate 8am, Journal 8:15am, Write blog draft at 6pm
  • Friday: Gym 7am, Yoga 7:30am, Meditate 8am, Journal 8:15am
  • Saturday: Gym 9am, Yoga 9:30am, Meditate 10am, Journal 10:15am, Write book at 12pm
  • Sunday: Nothing day

By the way, I find having a “nothing day” helps to recharge so I’m not having to be super disciplined every day.

Each day by 8pm, I text Emily how I did on my goals for the day.

For example, most days the text looks like this:

✅Worked on book

Or it may look like this:


Since doing a daily check-in with Emily, I’ve gotten much more consistent. We also do a weekly check-in over the phone (or in person when not in quarantine) to talk about our progress on our goals, what we’re struggling with, and what we want to work out for the upcoming week.

After making a few mistakes, here are a few guidelines I recommend following when choosing an Accountability Partner and establishing your check-ins:

  • Choose someone who you know is very disciplined that you can rely on to hold you accountable
  • Choose someone who you know can commit to doing regular check-ins
  • Set clear expectations for how frequent and what time you’ll do your check-ins
  • Set clear expectations for who’s responsible for initiating the call or text
  • Set clear expectations for how you’ll do your check-ins and when you’ll send your goals by

Whether you’re trying to establish a new workout routine, learn a new skill, or achieve a big hairy audacious goal (BHAG), I hope these tips and tricks help you on your journey to success! If you have any feedback or questions, feel free to hit me up on Instagram! 

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