4 Steps to Accomplishing Your Goals – Taylor Jacobson’s Story: “Appropriately Scary Goals”


This is part of the 4 Steps to Accomplishing Your Goals series, a walk-through of the process I use to accomplish many things throughout the year. I’m also highlighting stories from people who’ve accomplished big goals in their life or business.

Today, Taylor Jacobson shares why having a clear goal is crucial to motivation and prioritization. He’s currently working on Focusmate, the social network for productivity. Taylor’s a four-time founder, behavioral science expert, and Forbes Coaches Council member who’s consulted to well-known eight- and nine-figure startups. Using themes from behavioral science, Focusmate eliminates procrastination by giving users human presence and accountability at any time for any task through a video-based virtual coworking experience.

Check out past posts in the series to read more about clarifying your goal or creating a plan, and be sure to leave a comment about your experience.

The four steps each also have worksheets that help you walk through this process. If you want them, be sure to answer Yes!! on that section on the Insiders signup form (if you’re already signed up, you can update your profile by using the same email you used before).

Taylor Jacobson: “Appropriately Scary Goals”

Thanks for your time, Taylor. I’ve enjoyed my experience with Focusmate. Was there a moment when you decided that you really wanted to make this a reality?

The short answer is yes, but there was definitely an incubation period before that happened. I had the idea for Focusmate six or seven months before I committed to it. Right away I did a Skype session with a friend where we were just working, and it was effective enough that I think we did it five times that week. I knew it was something that could help other people. After that, I explored my curiosity around it. I did some testing, got feedback, and set up an initial test group of people.

Probably two months after that, I got to a point where I was spending so much time on it that I was a little worried that my day job was going to take a hit. I deliberately set it aside and forced myself to stop working on it for a little while to reflect on whether it was really the right time and the right project, because doing a startup just requires full, 100% commitment.

It was one of my clients who said to me that he thought I’d likely regret it forever if I didn’t do it. As soon as he said that, I knew he was right. It resonated with me. I pretty much made up my mind on the spot. At that point I was in.

You mentioned a little bit in broad terms that once you realized this was something you wanted to do, you took some action steps to make it happen. Can you go into a little bit more detail, and how those steps may have changed as you started getting into it?

Prior to this, I was doing leadership development and executive coaching. Part of the planning was knowing that I was going to stop doing business development, and that if I stopped doing a set of activities I was currently doing, it would pretty quickly impact my bottom line. I knew I had to clear the deck and make time for this.

I also talked to my fiancé, saying, “If I do this, then that’s how it affects our numbers together and what it means for us.” From the very start she thought it was a great idea. She was completely supportive, thought I could do it and be successful at it. That was definitely important to have our team be fully bought in and wary of the possible and likely compromises and sacrifices that would come.

More concretely on the business itself: there are so many things that you can do, and it’s easy to just start doing. Maybe this is obvious, but especially at that early, early stage, the only thing that really matters is selling something to somebody and making sure that there’s actually a business where you think there’s a business. The critical thing of early stage business planning is just getting a product out there in its most rudimentary form, getting a user, and then trying to sell the product to that user. That’s pretty much all I did. It was very unglamorous.

Is there anything that stands out to you that might be helpful to people who might be testing or starting a new project?

It’s hard because you always feel like what you’re putting out there in the world is just a pile of dirt. You’re like, “Hey, give me feedback on this pile of dirt.” For initial testing, I created a Facebook group where you could post in the group with the date and time, then people would respond in the comments and they would swap Skype IDs. It was very manual, but that was part one. I joined a bunch of Facebook groups where I didn’t know people, because I didn’t want to have my friends sugar coating it for me. I wanted to see if strangers were actually interested.

[… After validating the idea] I knew that there was very likely an opportunity and the only real next step was, “What do I need to do before I can charge people for this?” You have to be ruthless in trying to get to that point way before you feel ready. We talked about showing people your pile of dirt. Now you have to sell people your pile of dirt. I think we’ve done a really good job being extremely minimalist in terms of what we’ve built before charging people money.

It seems like you really focused on what was important and were able to prioritize that. Have you faced any challenges? You mentioned getting over that nervousness of showing people your work. Had you thought of this ahead of time? Did you made plans to try to avoid anticipated challenges?

I’d say no, I didn’t think about any specific challenges. Part of the reflection period before I committed to it was knowing that you have to go all in and know that it’s going to be hard, it’s going to take a while, and you still may not get to where you want to be. You won’t really know the outcome as you’re going through the process. Daniel Pink, the guy who wrote Drive, the book about motivation, says we’re motivated by autonomy, mastery and purpose. I think doing hard things and overcoming challenges is actually really fulfilling.

I’ve enjoyed all the challenges. A lot of the stuff I’ve had to do in this business I hadn’t done before starting, like trying to figure out how to build a functional prototype without knowing how to code. Also, really mundane things like legal stuff has been much more difficult than I anticipated. I go into it with the attitude that this is a normal part of the process, and I’m going to do my best, and that will definitely be good enough.

The thing that’s become clear for me, at least in this startup, is that nothing is that hard. It’s just been committing to being thorough, committing to doing my best, and committing to being decisive and not letting decisions drag out and dominate my life. We’ve got to keep moving forward.

That’s a good perspective and good advice, too. What else about yourself or achieving goals have you learned?

I feel much more effective in this current career iteration than I have in the past and I think it’s because of a few and underlying changes. Number one is definitely that I have to choose goals that are aligned with my values: aligned with the lifestyle I want to live and then aligned with just my values broadly. I have so many good business ideas. That’s been a source of distraction in my life. It’s really important to be rigorous about choosing projects that are aligned with who I want to be, what I care about, and the life that I want to live.

Kind of a corollary of that is aiming high enough, making sure I’m aiming high enough to be motivated. In the past, I’ve wavered between feeling like I should be doing something ambitious, from a sense of ego, or feeling like I’m not really capable of doing something ambitious. In this case, it was realizing that it’s a big goal, and that it would be really hard, but that it’s scary in the right way. It was appropriately scary for me and that’s been hugely motivating.

Some of the projects I’ve worked on in the past I could’ve executed much better than I did, but I didn’t because the place I was going to end up just wasn’t that exciting to me. It’s important to assume that big goals will take a while. Right from the get-go, have that mindset, because it’s a big goal, it will take a while, and that’s okay. That’s helped me be patient. All work is grunt work. No matter how sexy somebody’s job sounds, it’s all basically grunt work. Having really motivating, clear vision that’s long term also helps me put that day-to-day grunt work in context and feel like it’s all worth it and adding up to something really meaningful.

I’ve definitely been more rigorous with how I plan and prioritize this project. Some of that comes naturally from choosing something that’s appropriately motivating, because there’s no time to waste on the wrong stuff. Really being committed to making this work has helped me be rigorous in prioritizing. You don’t have to work that hard, you just have to prioritize, have to say no to things that don’t add up to the end goal.

Do you have any final advice for other people who are pursuing goals?

You don’t have to be perfect and productive all the time. I’ve spent a lot of time beating myself up for having a unproductive morning, day, week, or month, and feeling like I’ll never get anything meaningful done and that there’s something wrong with me. Now that’s really flipped for me, and I think we’re out-executing the vast majority of our peers in this position because we prioritize really well. I make sure I spend a few hours a day on stuff that really matters. If the rest of the day is a wash, that’s okay.

When I started working on this project, I had a very clear idea in my head of where it was going. I didn’t realize that until then, I’d never really had that clarity of vision before. Now that I do, I’ve found that for all the little stuff that I have to do on a day-to-day basis, I know exactly why I’m doing it. It doesn’t bother me the way it used to, and in the past I might have ignored some of the grunt work because I didn’t know where it was going to get me.

I don’t know that it’s necessary to intuitively have that vision. It’s possible that it’s the sort of thing that you can brainstorm and fill out that vision. For sure I won’t try to do a project again without just getting really viscerally, visually, tangibly clear on what it’s all building toward. That also helps with prioritization. Anything that’s not helping build toward that vision you have to say no to.

Prioritization seems to be the key thing here.

Yes. I’d say prioritization in the context of having the right goal, the right vision, because it’s a lot harder to stick to a plan without knowing where it’s going.

Thanks for your time, Taylor! Readers, be sure to check out Focusmate, and comment below – do you have a story of a time when having a clear goal helped you prioritize?


2 thoughts on “4 Steps to Accomplishing Your Goals – Taylor Jacobson’s Story: “Appropriately Scary Goals”

  1. Pingback: Press & Mentions • Focusmate Blog

  2. Pingback: 4 Steps to Accomplishing Your Goals – Shelly Najjar

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