Why Am I Not Achieving My Goals?

Lessons From Talking With Investors

This is is part of my live-learning series! I will be updating this post as I continue through my journey. I apologize for any grammatical errors or incoherent thoughts. This is a practice to help me share things that are valuable without falling apart from the pressure of perfection. 

Why am I not achieving my goals?

In this post, I explore goals that I have achieved or am on track to achieve as well as goals that I am failing to achieve.

I am doing this to provide clarity to myself and hopefully others asking the same question.

Defining My Goals

Here is a sample of some of the goals I am always iterating on and improving. 


Work less on unimportant tasks.

Spend more time where I’m not anxious.

Make $150,000 in personal income.

Find an executive assistant I can trust with my life.

Be more decisive.

To connect more deeply with a community.

To make new real friends.

2023 to 2033

This is in my thirties.

Make a million dollars after-tax in a year. 

Have a child.

Have a second house/accommodation in another city that I love. 

Sell a company.

Create and release a music album.

Run a marathon.

Public Goal Setting

I believe a lot in public goal setting.

It sets intentions. It increases accountability. It helps people understand what goals you are trying to achieve and how they can help. It helps you appropriately prioritize and deprioritize. 

I am currently building a public goal-setting Google sheet here.

Some would find this too vulnerable, scary, embarrassing or revealing. I think a life that you don’t achieve your goals is much more.  

Not Enough Focus

I am doing too many things at once.

Overly Ambitious Goals?

This is a difficult one to work through and why I’ve added a question mark.

For example, one of my goals was to be a millionaire by the time I was 30.

I’ve seen many people and even friends accomplish this goal. 

Growing up, people would say this is overly ambitious and maybe I have a small sample set skewing my perception of achieving this, but I do believe this isn’t impossible and is a good goal to have. Plus, a million dollars is a lot different than when I was growing up. You would need it to buy a small shack in Toronto. 

Lessons From Talking With Investors

Not SMART Goals

The SMART goal framework is used to help guide goal setting. SMART is an acronym that stands for Specific, Measurable, Achievable, Realistic, and Timely.

If you want to learn more about SMART goals this is a good resource.

Even above, most of those goals are not adhering to this framework and in a way that creates risk for achieving them. 

Not Dedicated Enough

It is okay to have ambitious goals but if you do you need to be focused on bringing them to fruition. Although most people would consider me a hard worker, I am not dedicated enough to the specific goals I am laying out. 

This leads me to:

Prioritizing Poorly

Don’t work hard work smart. That’s something that I know is important yet I continue to fail to do.

One of the recent quotes I’ve mentioned that has resonated with me is that it doesn’t matter how hard you paddle it matters what boat you are on. 

It doesn’t matter how hard I try to row (whether personally in life my kayak or professionally the boat at Speak Ai) if I am pointed in the wrong direction, don’t have the support I need, am paddling wrong or whatever other metaphor I could stick in here, I will not achieve my goals. 

Unsure Of Who I Am

This is a feeling I have felt disappear and reappear in my life.

Some days I feel aligned in what I am doing and on the right path and other days I wonder how did I get here? 

I wanted to be a hip-hop artist. I wanted to make music. Here I am at almost 30 years old trying to build a software company. 

Now that I have gone down this path it’s so hard to turn back. I continually try to realign myself and feel happy with the choices that I’ve made that have led me here but I often struggle to do so. 

When you have this existential angst, it often gets in the way of your goals. Or, you turn off a part of your brain that is having that angst and then go through the motions in the life you have built for yourself. 

Content like this is helping me address this. It’s me telling me to cut out the bullshit and address how you are feeling before you let more time go by.

Limited Role Models

This is also important. I find that I am unsure of who I am even trying to pattern myself off of. There are a few people that do stick out to me that I admire and that I think live a life both personally and professionally.  This may seem all over the place but here they are:

J Cole (Hip-Hop Artist)
Clem Delangue (CEO of Hugging Face)
Monika (My partner)

What do I consider a good role model? Someone who is successful personally and professionally who has balance in their life yet is driven, is stable, happy, experimental, curious, surrounded by friends and community (their tribe), knows they have support.

Haven’t Fostered A Community

This is something you realized as you look at either creators who built powerful relationships with audiences or organizations that have fostered amazing communities. 

As an example for creators, Tom Segura (a comedian) has built an audience through 10+ years of podcasting that supports him both online by watching YouTube, paying for live-streamed shows, sending in ridiculous clips and then paying when Tom comes and visits their cities for live comedy shows.

As an example for organizations, I refer to the company Hugging Face which has built a community of extremely talented developers who are leveraging machine learning, natural language processing and computer vision to create open-source technology that democratizes artificial intelligence. The passion in this community has driven investment, innovation and some of the world’s best talent. 

Without a community and supporters to help you achieve your goals, you are much more likely to fail. 

I’ve seen this play out in my own life. When I was in London, Ontario at the Innovation Works coworking space, I had a thriving community that lifted me up, connected me with others, and helped me navigate through challenges. When the pandemic came and I moved to Toronto, that community and connection unfortunately waned and the supportiveness of it all has collapsed for me at least personally.

I was on the way to doing the same thing at the DMZ when I moved to Toronto and it felt so right before the pandemic. But, we all know what happened there and we can’t go back. The world has fundamentally changed. So has the DMZ. So have in-person communities (at least in Canada for now).

I have been unable to find the same supportive network digitally. I know I could try harder but it’s exhausting and I know many of us don’t feel like spending more time on the computer even if it’s connecting to others. 

I do hope this resolves itself as restrictions lift. For this, I look to platforms and spaces organizing communities based on shared interests, stages of life, goals, geographical vicinity and more like MeetUp, TechTo, the Othership, Chocolate Groove, co-working spaces and conferences. 


Although people laugh at him, I always loved that Gary Vaynerchuk talks about patience. We are consumed by instant gratification. We see success stories around us without knowing the struggle, the intelligence, the luck, and the hard work that went into it. We think because someone else “made it” at 25 that we deserve to too. 

The truth is, I am still very early in my career. While things have definitely been tumultuous, I am still on an upwards trajectory and if I continue learning and improving that trajectory will take me to the places I want to be. 

Holistic Execution

I feel like that’s an unnecessarily abstract way to say that I am not taking care of my body, mind, soul, work/life balance, and personal/professional fulfilment.

To make it more concrete, if I go a week plus without exercising my mind isn’t as sharp and my decision-making drops in efficacy. I am not as happy during the day and I will have more difficulty sleeping at night. 

To achieve your goals, you need to remember that you need to take care of yourself. Treat yourself as a professional athlete and you will perform. Let the habits and activities required to make you healthy slide and even though it may feel like you are working hard you are jeopardizing achieving your goals. You will burn out, or isolate yourself, realize you’re bankrupting your spirituality and creating long-term problems.

While focus and drive are necessary for success and we’ve seen stories of the relentless CEOs and athletes forgoing all else for their goals, this is most likely not ideal. Either you achieve your goals and realize the other parts of life have been sacrificed. Or, you may still not achieve your goals and realize you have years to make up for important aspects of your life you never should have abandoned. 

Incomplete Team

This is also a difficult one to talk about. I’ve been building a small team over several years doing the best I can to attract and retain talent. But, as a self-funded company, I’ve struggled with this a lot. I don’t have the reputation, talent, network, mission and budget to attract the best people in the world. While I have an incredibly capital efficient, passionate team who has achieved a lot in our time together, it may not be enough for the ambitious goals I hope to achieve. 

Now again, this is my fault. And, depending on what I want to do, it is my responsibility to build or at least contribute to building or finding the team that can help me excel and achieve these goals. 

How to set good life goals?


100 Life Goals & How to Set Them | American Family Insurance
21 Life Goals to Set for Yourself (and Actually Achieve!)
23 Goals in Life to Set and Achieve for Personal Success – Lifehack
10 Life Goals You Should Accomplish in 10 Years | All Pro Dad

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