How to follow your goals without losing focus

A guide to embracing the chaos

Brooklyn Rose Ludlow
Upstart Tech
6 min readJul 23, 2021

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This is not a definitive, scientifically-tested way to achieve your goals. It’s just the way I think about my progress at this particular moment in time.

A preface: what really matters?

This is the big question. No one can answer it for you, and it can be hard to answer it for yourself.

What are you doing with your life? Where do you want to be in 5 years? What is your Purpose?

Even when you think you know the answer, it can drift and change into something different. This is because we, as people, are constantly learning, growing, and changing.

So what do you do about it?

Stay in tune with yourself. Pay attention to what you really want. You’re aiming at a long-term, slowly drifting target with incomplete knowledge of how to get there. The least you can do is check-in and make sure you like where you’re going. Try not to spend 5 years head-down in a frantic grind only to realize that you’ve ended up in the wrong place.

Moving Forward

So you’ve figured out “what really matters”; what you want your life to look like in 5 years. Good job. Well, now what?

You have to answer the question: “What is preventing me from doing this right now?”

And then be real about it.

Some common answers to that question might be:

  • A lack of mastery in certain key skills
  • A lack of experience
  • A lack of a concrete body of work that demonstrates your skills and experience
  • Life circumstances and unexpected changes
  • An aversion to risk or change

Look at other people who are doing what you want to be doing. Find out how they got there. Then deduce the commonalities in their stories and determine the key factors that led to their success.

The rest of your goals will be focused on answering the question: “How do I bridge the gap?”

Incompleteness

Your knowledge is incomplete. Unless you’re astoundingly lucky (or have a perfect mentor for your exact goals and life circumstances), you probably don’t know everything you have to do to bridge the gap.

Embrace the incompleteness.

If you’re constantly observing and updating, you may find new optimizations and better routes towards “what really matters”. Your progression will look more like a chaotic series of dashes and weaves than a straight line towards success.

In hindsight, you’ll recognize all kinds of missed optimizations that you didn’t know at the time. And that’s okay. If you had the knowledge to make optimally-efficient progress from the start, you probably waited too long to get started.

Goals: 3-month, 6-month, and 5-year. Nothing else.

So you’ve figured out your long-term target, and you’ve identified what you have to do to bridge the gap (to the best of your present knowledge). Now it’s time to give yourself some structure and start making progress.

3-months

3-month goals are your immediate plan forward. The best path is based on the knowledge you have right now with problems that are immediately actionable for you to solve. The trick is to find a balance between pushing yourself and being realistic about what you can achieve in ~90 days.

6-months

6-month goals are a guess. What do you think your 3-month goals will be 3 months from now?

And once you get there, you can reflect on how and why they’ve changed.

1-year

1-year is a quantum superposition. Don’t bother trying to understand it. Just keep a vague intuition in the back of your mind and recognize that your 1-year outlook is apt to swing wildly based on your short-term navigation.

5-year

5-years is the destination. “What really matters”.

The problem is, it’s always 5 years away. So make sure that you stay in tune with yourself and try to embody “what really matters” every day of your life, even if you haven’t made it all the way yet.

Chaos

You can try to fight it. Or you can embrace it and make it a core component of your plan.

Good chaos: Recognize when the ordering of your subgoals doesn’t matter.

You don’t have to make a rigid plan upfront and follow it to the letter. You just need to move in the right direction.

If you’ve followed this guide so far, you should have a list of things that need to be done to bridge the gap. Many of these can likely be tackled in any order you want, so pick one and get started. Choose what makes sense to do based on where you are right now or just choose the direction you like most and see where it leads. If one path leads to a dead-end, pivot and try something new. If you’re starting to get burnt out on one task, pivot to something else.

There are costs to pivoting (more on this below)–but when it’s done effectively, there can also be great advantages.

Good chaos: Consider the bizarre and unintuitive

While you’re planning goals, make an effort to consider bizarre possibilities that you’d never think about normally. “What if I went job searching in Germany?” “What if I gave away all my non-essential possessions and became a digital nomad living out of a van doing remote tech gigs?” “What if I took the time out of my schedule to walk down to the park and watch the sunset every day?”

Some of these are non-starters, but one of them might be the most valuable decision you’ll ever make.

Bad chaos: Don’t be a dog chasing cars.

Or else you’ll jump from skill to skill, never focusing on one thing enough to master it.

“Should I scrap my current goals and spend 6 months learning data engineering to get a job with a hip Silicon Valley startup?”

Well, maybe. How does data engineering fit into your 5-year plan? Are Kafka and Spark things that you care about or were going to learn anyway? Is this something you enjoy doing?

There are inherent costs to pivoting like this. You shouldn’t jump on something just because it’s “an opportunity” (hone your skills to a high degree and you should find no shortage of opportunity). Instead, go after things because they align with your long-term goals and help you develop the skills you need to live your best life.

Some good reasons to pivot include:

  • Finding out that skill you’re working on isn’t important. There are other ways to achieve it or other skills that can replace it.
  • An opportunity comes up that closely aligns with your long-term goals and is worth changing your short-term course for, even with the costs of pivoting considered.
  • Something changed in your life that makes the cost of continuing on your current path higher than the cost of pivoting.

Life is chaotic. Your playing field won’t be the same from moment to moment. New opportunities arise, discoveries are made, and new obstacles may appear. You should always be alert and ready to pivot if one door closes and another one opens. As long as you keep your eye on “what really matters” and move in the right direction, you’re making progress.

And in conclusion

That’s it. Figure out what really matters to you, prioritize it, and be ready to adapt and optimize at every opportunity.

I might change my mind on all of this in 6 months, but that’s the beauty of this whole thing.

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Brooklyn Rose Ludlow
Upstart Tech

Brooklyn Rose Ludlow is a data engineer at Upstart and freelance jazz musician.