How to accomplish complex goals
Systems progressing despite uncertainty
For goals like reading a book, tidying your apartment, or completing a course, it’s clear what you need to do. It’s mostly a matter of finding the time and motivation to complete them. However, many goals don’t have such clear steps to follow. Goals like increasing your income, improving your wellbeing, or reducing conflict in your relationship don’t have clear steps to follow. Half of the challenge is figuring out what to do.
Complex goals like these tend to be the ones we procrastinate. The ambiguity of where to start prevents us from trying anything. As a result, we never experience a sense of progress that can fuel the motivation to continue.
This article is about overcoming that challenge. It’s a summary of the tactics that have helped me accomplish meaningful goals where the steps to achievement weren’t clear. I’ve organized those tactics into two categories: tactics for getting started when you don’t know what to do and tactics for actually progressing those goals.
Tactics for getting started when you don’t know what to do
How can you make a plan when you don't know what to do? The crux of these tactics involves either clarifying the outcome you want or increasing your understanding of the challenge you want to solve.
On the surface, these recommendations seem obvious, but nonetheless, in my experience, people don't implement them. Before you throw up your hands and give up on a goal because you don't know what to do, scan through these recommendations and make sure you have tried them.
Backward planning - To break through the uncertainty of how to progress toward a goal, you can start with the end in mind and work backward to define the steps you need to take. Typically, when people think about a goal, they plan forward by asking, "What are the next few steps I need to take?" The downside of forward planning is that you waste effort on tasks that don't directly impact your ultimate goal.
For example, I vaguely intended to build my own products for years, believing my work as a product manager was good preparation. While partly true, it wasn't the most direct path. I thought I needed extensive experience to quit my job, get funding, and start a company. Eventually, I realized I could simply start making something immediately. Working backward revealed a more direct route to my goal.
Ask for help - It never ceases to surprise me how productive it is to ask someone for help. I often spend hours thinking about a work problem, making very little progress until I stop and ask for help. Even if the person has little understanding of the issue, simply explaining it clarifies the problem in such a way that the solution becomes self-evident.
It's also incredible how willing people are to help. When I started exploring the idea of building a mobile app to overcome procrastination, I emailed world-renowned researchers, best-selling authors, and notable practitioners to pick their brains on the best approaches to helping people overcome procrastination. To my absolute amazement, they almost all responded and agreed to meet with me to help. It reinforced an important lesson: don’t be shy about asking for help!
You don't always need an expert, though. Software developers use a technique called "Rubber Duck Debugging," where you explain your problem or code in detail to an inanimate object, like a rubber duck. This process works because it forces you to articulate your thoughts clearly, engaging different cognitive processes and highlighting gaps in your reasoning. By verbalizing each part of the problem, you often gain new insights and identify overlooked solutions.
Ask AI - No offense to humanity, but some of the most helpful coaching I have ever received is from an AI. I now routinely explain any problem or challenging goal I'm working on and ask for help. Tools like ChatGPT and Claude are incredibly good at brainstorming ideas for how you could progress your goal.
You also never need to worry about keeping up appearances. The AI doesn't care that you don't know obvious facts about the world, it doesn't care about your most shameful thoughts, and it doesn’t need you to ask sensitive questions delicately. You can just ask!
Try something - It's stunning how common it is for people to have problems in their lives that they themselves describe as costly and significant, yet spend almost no time trying to solve them. Consider the biggest problem in your life; it could be chronic stress, financial instability, or poor health. Ask yourself, "In the last month, how many hours have I spent intentionally trying to solve this problem?" Not just worrying but brainstorming and testing solutions.
If the answer is zero, you might not need especially sophisticated advice; you just need to try something. One of my favorite YouTube creators, MrBeast, famously won't help other creators until they've made 100 videos because most improvement comes from simply trying. The same applies to personal goals. If you haven't tried anything, stop reading and start doing.
Tactics for progressing challenging and ambiguous goals
Once you start working on a challenging goal, you sometimes get to the point where the ambiguity of what to do paralyzes you. At that point, it can help to go back to planning steps like asking for help. However, you can also implement a few simple habits to help you repeatedly overcome the ambiguity and maintain resilience.
My article on how to be consistent outlines a general system for maintaining your focus while working on long-term goals. However, some of the recommendations in that article, like visualizing your progress and creating an accountability group, can be hard to implement when you don't exactly know what you're doing. The tactics below specifically focus on that scenario. They are a few simple habits that will help you achieve complex and ambiguous goals.
Focus on the process - When you're not exactly sure how to progress a goal, it can help to focus on the processes that will lead to achieving your goal. For instance, when I first had the inclination to build my own product, I had no idea what I was going to do. So I teamed up with my good friend Kemble and agreed to watch and discuss one episode per week from Y Combinator's "How to Start a Startup" series. Eventually, we identified chronic procrastination as an important problem to solve and ultimately built the Doer mobile app.
One of the most powerful systems I've developed based on this idea is a daily workbook. The exact design of my workbook changes from time to time, but the core habit persists: every morning, I open my computer and update the workbook. Sometimes, I spend an hour working on my goal, and other times, only five minutes, but I do it every day.
Stop and reflect - Each day, week, or month, take a moment to pause and ask yourself three questions:
What has gone well?
What hasn't gone well?
Is what I'm doing impactful, or do I need to try a new approach?
One of the benefits of doing this is that it allows you to course-correct and learn from experience. This is critical when working on a goal where you don't know exactly what to do. It's like checking a map during a hike: the more unsure you are of your direction, the more utility there is in regularly checking your location.
As a product manager, one of the most impactful habits I have adopted is keeping a work journal. It's not uncommon that after days or weeks of working on a project, I answer the questions above and decide to entirely abandon it and try a new approach. In a professional setting, there is a strong bias against abandoning projects, so in my observation, employees and companies waste enormous amounts of resources because they don't take time to pause and ask if they should keep going in the direction they started.
Over-celebrate milestones - Whatever your goal is, pick a point in the future to celebrate. If you're working on a product, it could be getting your first user; if you're trying to be more confident, it could be asking your first question in a meeting. Whatever it is, over-celebrate it. Reward yourself with something meaningful.
Recognizing and celebrating milestones reinforces the behaviors that lead to success, increasing your resilience. I have tended to neglect this throughout my life because I've held onto the belief that I should only celebrate when I'm finished. However, the end may never be in sight for challenging life goals, so you have to pick something to celebrate.
Work with someone else - I’ve mentioned this in other articles, but it is worth repeating. In my view, teaming up with someone else is one of the most underrated strategies for working on personal goals. When working with someone else, you get accountability, coaching, motivation, and new ideas all for free! Just because it's a personal goal doesn't mean you need to work on it alone. It's unlikely that you are the only person working on your goal, so it's worth putting in time to find someone you can team up with.
This is especially true when what exactly you need to do is unclear. For instance, 75% of startups valued over a billion dollars were founded by a team. Working in a team is so important that many of the most famous startup accelerators, like Y Combinator, strongly discourage people from starting a company alone or even having unequal equity splits!