Why Your Goal Setting Process Is Broken And What To Do About It

Pia Silva, Contributor/Jan 3, 2018

Yes, this article is about goal setting. But rest assured I’m not repeating the same garbage you’ve already seen a million times this week.

Most people start goal setting by thinking about all the things they want to accomplish this year. Then, if you’re a seasoned goal setter, you probably write them down, and work backwards to create mini goals to make them actionable.

Many people fail to achieve their goals because they identify an outcome without also identifying the underlying motivation of that outcome. Without knowing your intentions, you make it too easy to sleep in instead of going to the gym, or let blogging fall by the wayside when more important things seem to come up (they always will).

Setting yourself up for a successful year means getting clear on what you’re really going for and why —before you make a list of what you want to achieve. If you’re committed to really achieving something big this year, give your goals the focus and time they need to thrive by laying a better, deeper groundwork first.

Dream Outside Your Normal Space

For the past four years, Steve and I have gone on a retreat to do our visioning for the new year. Some years, we are able to get away and do it in places like Tortola or Maui, while other years it’s a trip to our local coffee shop. Either way, we make a point to get out of our normal spaces to dream, plan, and strategize. For at least one full day. (Just putting the day aside is always goal #1!)

When we did this in Hawaii we had no electricity; just moleskines and books. Since we were without distraction, we were naturally focused and inspired to dream big, and we came up with all kinds of new ideas for our businesses and our lives that hadn’t been on our radar previously. Years later, many of the big goals we set on that trip are in place today, though they look at lot different.

That’s the year we reread Rich Dad, Poor Dad and decided we needed an income-producing asset. Since we couldn’t afford real estate, as he suggests, we brainstormed other opportunities that would utilize our most valuable asset: our experience. Though it took a full year and a half to actually start producing income from it, we were able to build an online course.

Creating an online course (the passive income so many desire) is a long and arduous road I’ve talked about before I’m pretty sure we would have quit before our course produced results given how much time and money it took to make it work. But I had laid the groundwork to create something that went beyond “passive income.” I wanted to be able to free up a specific amount of time so I could write a book and use it to build a community of like-minded entrepreneurs. That goal dwarfed the money spent. Instead of thousands of dollars down the drain it was a clear investment into a future payout, one I was not willing to give up on.

The process we used to envision and create the goal of an online course has produced (and continues to produce) serious results for us. It became the standard for all our future planning and visioning sessions. Hopefully it can influence yours as well.

Our Unique 3-Step Process

First, the biggest difference in our process is that it focuses on identifying how you want to feel in your life. The goals and achievements are just things. How it changes your experience of your life is what we’re all really going after, and if you can start with that, you’ll be infinitely better set up for success.

So here’s our three-step process that has never failed to produce big results. It requires commitment, so your first task is to set aside a full day to just focus on this with no distractions. If that sounds like too much or you don’t think you need a full day, you are already communicating to yourself that these goals are not as important as you say they are.

STEP ONE: Toast Your Accomplishments

Goals are about the future, so why would we bother talking about the past? Because before we look forward, we want to prime our mind with our success. That’s why we actually start by taking a look back at how much we’ve accomplished. Doing this makes me so enthusiastic and excited because I’m always pleasantly surprised at how much I actually did in 12 months! And when you start your goal setting through that lense, you realize it’s not that crazy to say, “I want to be all the way over there in 12 months.” It makes dreams seem more accessible. It makes me believe in what’s possible.

That’s why Steve and I spend the entire first half of our strategy day talking about our accomplishments from this past year. It takes us half a day (usually 9am – 12pm) to really identify all the things we have done and to recognize where we were a year ago.

When you think about it, a year is a long time and you can do a lot. When you sit down and write about all of your accomplishments, all the things you’ve learned, all the things you’ve failed at, and how you moved forward, it’s an incredibly energizing way to start planning for the next year.

Get as specific as possible. We count as accomplishments our general wellbeing, vacations, books we’ve read, fights we’ve had that we resolved, and things we tried and failed at and learned from. If you’re not failing, you’re not trying that hard, and trying new things is something we’re always striving for.

So before you do anything about the future, I want you to sit down and take a lot of time to write out all the things you accomplished this year. Write them out in terms of your career, personal well being, and your family. Write them out in tangible things and intangible things. Both. (I felt calmer this year, or I didn’t feel calmer this year but I took steps to feel calmer can be accomplishments.)

Then, toast yourself and go to lunch.

STEP TWO: Big Picture Strategy

If you’ve done goal setting and planning before you’ve probably written down “the big goal” at some point. Now is the time revisit that big picture goal. Things change, and they should! And before you continue down a path that you’ve been on for years, it’s worth rethinking if that’s even what you really want anymore, or if it’s just a default at this point.

Are you still excited about where you’re heading? Is it still big enough for you, or have your britches gotten considerably bigger over the past year?

Many call this your BHAG (big hairy audacious goal). Audacious means to take “bold risks.” This goal should stretch you.

We revisit ours each year because it often does change. Years ago we were on a path to build a huge agency. When we realized we wanted the agency because we wanted freedom and flexibility, we realized we would prefer a completely different BHAG and that we could achieve freedom and flexibility much faster a different way, rather than building a huge business with a high gross revenue and an internal team in order to make enough money to have freedom. We were on that path going full force until we were forced to question it (failure and debt will do that to you) but now we purposely rethink the BHAG on at least a yearly basis.

Once we’ve revisited our big picture goal, we move into our one-year goal. We ask ourselves, “Where do we want to be this time next year? How does this push us towards our BHAG?”

We define it by intangibles like, “How do we want to feel? What does it feel like to achieve those things?”

We spend a lot of time describing what it will feel like to accomplish these things because, ultimately, accomplishing the goals is less about having the things, than it is about how those things are going to make you feel. This part is magical because even if you didn’t quite hit your goals last year, if you feel the way you wanted to feel, you still ultimately got what you wanted and that’s something to be happy about.

For example, you might set a goal of hitting $20,000/month because you want to feel financially secure, but if you hit $15,000/month and are on a path for growth you feel confident about, you will likely still feel financially secure. So didn’t you then actually hit your goal?

Likewise, you may hit $20,000/month and still not feel financially secure, in which case you’ll learn that it was never about the money. That is a good sign that you should investigate those feelings instead of always trying to make more. In that scenario, more money will probably never make you feel financially secure, and that’s good to know before you spend your whole life always chasing money to achieve security, and never achieve it.


This is where most people start their goal setting; stating their goal for the year and then listing how to get there. It’s still critical, but without steps one and two it will be infinitely harder to follow through.

The last thing we do is work backwards to break that one-year goal into six month, three month, and one month goals to identify actions we need to take. We then turn our answer into SMART goals: specific, measurable, achievable, relevant, and time-bound.

We get really granular about the steps we need to take each week to meet these monthly milestones. Steve and I share a spreadsheet where we write weekly goals based on the monthly goals. These are specific and they have due dates for the following week. Every week, we go into the spreadsheet, record if we accomplished the task (or not), and set our next week’s goal.

We’ve all heard that you’re more likely to achieve a goal if you write it down. One study showed that 76% of those who write their goals down, rate their level of commitment, share it with a friend and check in weekly actually achieved those goals or were in the process of achieving them, compared to only 42% of people who just thought about their goals. If you want to make it happen, it’s valuable to write it down on the shared list and commit to revisiting it frequently.

And while we’re scheduling things, take a minute to schedule quarterly check-ins now to make sure they happen (what gets scheduled, get done), even if it’s just a couple hours at a coffee shop every few months. By planning to check-in with yourself throughout the year, you’ll make sure you’re still on track. If you’re not, you can make adjustments instead of waiting until next January.

Go Beyond Your Business

This strategy can be applied to other areas of your life as well. We have friends with kids who use a similar strategy for family goals. It’s easy, when you’re married with kids, to assume the other person is on board or is still the person they were five years ago. These retreats help ensure their shared values and family goals are the same.

Whether you’re plans are personal or business, make sure you’re not just trying to get more stuff, but that you identify what you want to feel when you get the stuff. If you don’t get a hold of what you’re trying to accomplish, and ultimately how you’re going to feel and live your life, you’ll end up with a bunch of things and none of it will matter. You’ll just want more of it.

There are many paths to accomplishing your ultimate goal, and you may be able to get there sooner than you think if you take a different path. Be open to that mindset. It’s amazing how far you can go with a clear vision and accountability. Cheers to your most productive—and personally enriching—year yet!