Working out what to do next in your career

Photo by Annie Spratt on Unsplash

I spent the last month trying to figure out what to do next in my life. What should my career be, what do I care about, and why? I went down many avenues — from yoga and ancient texts in Indian spirituality to building spreadsheets and attending job interviews. This month has transformed my beliefs about myself and my understanding of what I want to do. I’ve found some answers to hard questions.

I want to share with you the approaches that helped me, roughly organized into a course that you can follow yourself. This time and process has been very valuable to me, and I’m happy to help others on this path. If you’d like some help along the way, email me.

This article is written around what helped me and worked for me, with the hope that some of it also speaks to you and helps you. There is a distinct entrepreneur-flavor to it. I cannot promise it’ll all be relevant, but hopefully enough will be to make it worth reading to the end. Hopefully you try out some new things. Please let me know how it goes!

Where you are now

I’m assuming you are looking to make a change in your career. Perhaps your previous work has come to an end, or perhaps you have the gnawing feeling that what you’re doing just isn’t right — it doesn’t satisfy you, you’re bored, you need more challenge or perhaps you need some more variety. Perhaps you’ve known for a long time that there are other things out there you want to do, but you’ve never worked out how to get there.

First of all, your situation does not constitute failure. There’s a strong unwritten rule in our society that if you don’t love your job right now then you’ve failed in building your own personal Maslovian pyramid. This is totally insane. It’s ok to experience boredom. It’s even healthy to get comfortable with it. You are not your job. Knowing that things are not quite right is a valuable signal for you, it’s what helps you to make changes.

Secondly, this can be scary. You might feel scared, not knowing where your life is going. You might have been ignoring these questions, and now you have to face them. This might all seem daunting, to explore all the possibilities and do the work of figuring out what you want to do. Change is scary. Maybe you’ll learn that you need to make bigger changes in your life, or that you need to make hard choices between different things you want. You might have to accept that there are sacrifices to your current living situation and income to get to where you want to be.

It might be that some things have changed in your life recently. It could be that your work has changed, or your personal life has changed, and this has brought you to consider these questions now. I had a painful breakup and it removed a supporting pillar from my life; with that gone, I was forced to examine the other foundations and strengthen them. If you’re going through other hard changes, then the work you need to do now to take care of yourself and find answers will be harder — make sure you have the support you need (see the next section). If you need to, take time first to deal with the problems or change in your life, in preparation to later explore questions about your career. If you need to, seek out appropriate professional assistance (perhaps a therapist), this article is not a replacement for that.

Where we’re going to go

We’re going to embark on an adventure, through your own realms and inner yearnings. We’re going to try and answer the question of what you want to do next. This will involve desk research, meeting people, putting yourself out into the world, reflecting, creativity, meditation.

You can think of this process as opportunity-farming: We want to sow a lot of seeds and see how they grow. Some will be fruitful, others not. For each opportunity, you’ll evaluate how you feel about it and if it’s what you want to do next. Through this process you’ll gain self-knowledge and more options in your life.

It’s going to take time and effort. And it’s going to be interesting and fun.

How long will this take?

To do this you’ll need time to yourself. Time when you are well enough rested to think through things (so not just before bed after a hard day at work). Time when you have enough peace and freedom from distractions to let creative thoughts start to flow (e.g. blocks of 30 minutes to a couple of hours). You’ll need many of these sessions, so that you can build your thoughts and explore your earlier thoughts.

You will also need time to meet up with people and talk to them about ideas and opportunities. I quickly found that I was very broad in my ideas of what I might want to do, so wanted to meet with many of different people. This takes a lot of time (I mostly met people face to face).

To do all of this, I spent three weeks solely focussed on this process. I found dedicating this length of free time to the process really worthwhile. It’s not often we have this much free time to ourselves; in this case find the best way you can fit time for reflection and time for meetings around your other responsibilities and expect this journey to take quite some time — perhaps a month or two, depending on how much time you carve out each week. It’s hard to give a precise formula for how much time you need, think to yourself how big your questions are and how much time you can find per week to work on them, and set a timeline you can dedicate to working on this process.

In a lot of conversations I had over the last month, other people told me about their searches for what to do next. And when I said I was spending a month on this, some people chuckled and said “Just one month?”. It turns out many people have spent quite some time exploring the question of what to do next. Some spent multiple years. I found it comforting that other people find these questions hard as well. I found my month to be a really valuable and formative period — I didn’t end it with my questions totally answered and a new job in the bag, but I did leave it with a lot more clarity, feeling much closer to an answer and having tangible steps forward.

Tools and process

In this section I’ll outline the activities that’ll drive this process and tools that will help. Feel free to modify this to fit your needs — perhaps you want to add some activities, remove others, add some extra tools. Also, experiment — try out different activities and see what works for you. Try something new, out of your comfort zone.

The tools section includes things like yoga, meditation and journalling. I’ve definitely been influenced by living in California! However, if these practices seem overly fluffy or intangible, take a moment to google the evidential basis for them. We’re at a fortunate moment when science is starting to take more interest in practices like journalling, gratitude and meditation and we are starting to build evidence for what works. The field of psychotherapy is also developing evidence-based-treatments, like CBT, bringing more clarity to a complex field.

I also include things that will boost your creativity and openness. Sometimes we get focussed on a narrow set of life-options, and now is a great time to look more broadly. Even if you end up staying close to your current career path, you’ll have fresh conviction that this is where you want to be.

Tools

Support

This process is like a spring-clean for your mind and motivations. It’ll be a lot of work. It should take you to some uncomfortable places. You may have come into this with change or upset in your life. Therefore, it’s most important that you have enough support to do this.

Support comes in a lot forms:

• Bouncing your ideas of people to see what they think of them (“Should I become a fire-fighter?”)
• Sourcing new ideas (I found many unexpected ideas from open-ended conversations with people in my industry)
• Having your incorrect negative beliefs challenged (“I’ll never find a job”, “I cannot do sales” ...)
• Sharing the load when you feel overwhelmed or stressed

There are many people that are good to talk to:

• Friends
• Family
• Partner
• Therapist
• Colleagues and people in your industry

This whole process brought me closer to my parents. We’ve talked a lot more often on the phone, and it’s been really nice.

Many people I know have praised having a therapist, and many entrepreneurs have publicly said they wished they had done it sooner. I’ve really enjoyed working with two therapists (a personal one, and a couples one). If you’re not familiar with therapy, think of it as a mixture of having a personal trainer for your mind and having a caring person that you can share your struggles with. It’s nice to have someone who (unlike friends and parents) you don’t feel bad “burdening” with your struggles and negative feelings. Furthermore, they understand human minds well and can help you learn how to better live with your mind. Therapy can unfortunately be expensive, although there are some cheaper alternatives emerging which may also be helpful (some listed below).

Therapy-like apps:

• Woebot: Chatbot offering range of therapeutic methods
• Stoic: Journalling, meditation, Quotes, Cognitive behavior therapy
• Quirk: Cognitive behavior therapy
• Headspace: Guided meditation
• Insight timer: Guided meditation
• Aura: Guided meditation
• What’s up: Cognitive behavior therapy and many other similar tools

Self-care

Make sure you’re taking care of your basic needs:

• Get enough sleep (eight hours for most of us)
• Exercise (anything you enjoy, ideally at least every other day. One hour of exertion in the morning can noticeably boost your mood and productivity for the whole day)
• Have some downtime from work and responsibilities to do things you enjoy
• Find some solitude to recharge and think clearly
• Eat healthy(ish) fresh food you enjoy

All of this helps give you a positive well-rested mind, ready to take on new challenges.

Mindset

As you set out on in this inner journey, your own mindset is the foundation you’re going to build on. Positive-thinking style self help can seem a bit corny, but for the purpose of considering your possible futures, optimism and open-mindedness allow you to see many more options than you realized were open to you.

I’m going to list the properties of the mindset you want to cultivate during this process. Think of this list as a navigation aid: check in with yourself and explore if you’re experiencing these properties, or their opposites. If the opposite, gently reorientate yourself, even if for a moment, towards the desired state. This is an ongoing practice (see the Meditation section for ways to work on mindset). As you become more self-aware of where you currently are, it’s easier to intervene and spend more time where you want to be. Most important of all, do not judge or criticize yourself for your mindset — accept and love where you are, and do a little work to be where you’d like to be.

The properties we want to cultivate:

• Abundance and optimism: We tend to be in one of two beliefs: the world provides abundant opportunities, or the world provides very few (scarcity mindset). This can be a powerful force on our actions, and on what we consider our options to be (Ben Ling’s book vividly explores this in today’s America). The reality is that around us are eight billion people, and more lives and paths than we could ever catalogue. You might feel that you already know what is in your sphere, but we’re going to push outside of it and find much more.
• Open-mindedness: You know yourself quite well. Your understanding of yourself has lived observing yourself for quite some time. It’s easy to believe you know everything there is to know about yourself. But, you don’t. I’ve been surprised to see how I reacted to new experiences and considering roles that I had for a long time assumed “wasn’t for me”. Hold an open mind about yourself: what you could be, might want to be, could do. Instead of short-cutting and filtering out opportunities, we open to exploring them and seeing how you feel about them.
• Curiosity: Children rapidly learn about the world thanks to their curiosity. If they see an object, they’ll pick it up to see what the bottom looks like. After sitting in one spot, they’ll try out all the other spots. You’re going to harness curiosity to bring yourself to more opportunities. Curiosity is a form of play, it’s fun and and it doesn’t have goals. Curiosity means listening to the (perhaps very quiet) signals in your brain saying “hmm I wonder what is over there…”. Allow yourself to wonder about something, to learn about it more, and follow the rabbit holes to other places. Examples of this are browsing lists of companies and reading their stories, trying out a new hobby or art, asking people about things for the sake of learning about them. Take meetings with people even if you’re not sure that you’re interested in working with them, be open to helping them however you can and then be surprised by what you find.
• Unlearning old stories and beliefs: Our interior voice constantly weaves a strong dialogue about who we are and what we can do. Over time we accumulate a list of beliefs about ourselves that we don’t even try to challenge. You may find it incredible to list your limiting self-beliefs and challenge each of them because you will find that they’re not as true as you think they are. Like most things in this article, to get the benefit this will require you to put in effort, and work repeatedly over time. If you can open up any more avenues to yourself, it’s incredibly valuable work.
• However you want to spend your time is the right thing to do: Give yourself the gift of free time, unburdened by goal or judgement of whether you “spent it well”. This process is one of creativity and discovery, and continually trying to measure your productivity will collapse your creativity mode into an execution mode. If you don’t feel engaged with your plan for a session, let go of the plan and do what is calling out to you. Perhaps go to the gym, or do something creative, or go visit the cat rescue center you’ve always meant to visit. Who knows what you’ll find there, and you’ll feel nourished and ready to do more things afterwards. If you find yourself judging yourself over how you’re spending some time, recognize that, thank the thought, and gently let go of it.
• Self-love: Our inner critic continually likes to tell us the ways it thinks we’re inadequate. It likes to portray us as unfinished works and remind us we need to hurry up and complete ourselves. It likes to obstruct loving yourself. All of this is an extra burden to your journey. The truth is, you are as complete today as you will ever be, and the critic will always want to criticize. Therefore, you have a choice: to hold on to this feeling of inadequacy, or to start to let go of the critic and embrace feeling complete and peaceful now. And loving yourself. This is much easier said than done! But starting down the path is incredibly valuable. As well as meditation (and various spiritual practices) to relax the grip of the inner critic, simple gestures of self love are helpful: compliment yourself, do something just for yourself, improve your environment, be easy on yourself, write a love letter to yourself, take a moment just to appreciate being you, spend time with people that love you and acknowledge their love, log gratitude, do yoga, dance, breathe, play.

Meditation

I’ve found meditation a really useful practice to support everything in this article. If you’re unfamiliar with meditation (and perhaps understandably skeptical), here is how it’s tangibly helped me:

It is an exercise for your brain that makes you better at certain useful things:

• It makes it easier to be self-aware of your automatic thoughts and circular thought patterns, which lets you intervene quicker with more productive reactions
• It makes it easier to be a detached witness to your emotions, instead of being controlled by them (e.g. you can better respond to anger or jealousy with curiosity rather than aggression or sadness)
• It makes it easier to quieten your inner voice (aka the critic) and to place less importance on the things it says to you

Also:

• It gives you some time to introspect where your mindset is at and reflect on that
• It de-stresses you by providing a moment of respite from the day
• It provides a quiet moment where creative thoughts can bubble up
• It relieves feelings of anxiety and depression (although if you’re experiencing significant levels of either, explore other treatments)

A huge number of successful individuals and public intellectuals advocate meditation, and there is some scientific evidence for its benefits.Meditation (in various guises such as prayer and private contemplation) has been advocated by a lot of religious traditions for a very long time.

Meditation is nothing mystical nor complex, it can be done almost anywhere at any time. For a very simple introduction, set a timer for two minutes in a quiet place and just listen to the sound of your breath. You’ll probably come out feeling less stressed and more positive.

I believe that regular practice is more important than any particular style of practice. Building up to 10–30 minutes, and doing multiple mornings per week has been really helpful to me.

There are many possible formats for meditation:

• Mine is really simple: A Spotify meditation music playlist and my phone’s countdown timer
• Apps offer both simple timers and guided meditations: Headspace, Aura, Calm, Insight Timer
• Search for a local meditation/zen/Buddhist center that hosts group meditations
• Vipasana and Transcendental Meditation (TM) have a lot of fans

Yoga, is at its heart, a meditation practice. There are a million different flavors, some focus more on the fitness side of it, others focus more on the meditative and mindset side of it. Try some different teachers and see what you enjoy. Personally, I find yoga a great way to start my day, lift my mood and adjust my mindset. Over the last month I frequently visited a nearby studio and I found it invigorating.

Breathwork

Whilst I’ve got you on the meditation track, I’d like to introduce a lesser known practice: holotropic breathwork. I recently discovered it and have been blown away by its usefulness. I’m really surprised it’s not more popular given its simplicity, safety and effectiveness.

Breathwork is pretty simple: it’s typically an hour (or longer) session, and involves no equipment other than your own breath and a comfortable blanket to lie on. In a session (usually led by a facilitator) you perform a strong, intense breath (in to the belly, then in to the chest, then out fully) quickly and repeatedly without breaks. This is where the “work” part of the name comes in, you have to make a real effort the first five to ten minutes to keep at it until a flow kicks in.

The decreased carbon dioxide levels in your body gives you a sort of high, delivering a state of altered consciousness (a grand term just meaning that your inner voice kinda goes away or operates differently from normal). Often the facilitator will help you set and revisit intentions and also let go of tension or emotion you’re holding onto.

In the practice I experienced a bunch of benefits across two sessions:

• A strong feeling of positivity and possibility
• Letting go of grief and emotion from my breakup
• Intense feelings of self love and inner beauty
• Finding compelling visions for what I wanted to do next in my life and what I could become
• Generating more ideas of career paths to explore

I found those benefits continued after the sessions.

Curiously, breathwork was adopted by some US based consciousness researchers when they were banned from continuing their research into the effects of LSD. It seems there are some similarities between both for helping people have therapeutic / mind-expanding experiences, as well as helping with addiction.

I’d encourage you to explore this tool. You might have to search around and travel to find a breathwork class.

Journaling

Journalling is another helpful practice for our goals. The type of journalling I’m referring to here is of writing down your thoughts, when they occur to you. I find this helpful for a few types of thoughts:

• Negative thoughts — writing them down lets you challenge them, and realize why they are not quite true
• Breakthroughs and insights — writing these down helps me “lock them in” and return to them later to re-examine/reflect on them
• Ideas — Every time I have an idea (e.g. a job I might want to do, business I might want to start, role I might want to work in, title I’d like to write, idea for a poem) I write it down. I then later look through my lists and see if there’s something in it that peaks my interest, and then explore it more. Don’t filter your ideas at this stage, just write them down.

Reading and writing is a way of kneading your thoughts. As thoughts move back and forth between mind and paper, they develop, form structure, can be broadened or refined. There is also a release to writing things down, the act of expressing them is therapeutic in of itself. Finally, writing down a thought relieves you from having to hold on to it, as you know it’s safe for later — freeing up your mind to think more.

There are lot of apps out there for journalling, as well as plain old pen-and-paper. I personally use Apple Notes as it syncs between my phone and computer, is free and lightweight.

Reading

In this process you are opportunity farming. And an important fuel for that is bumping into new ideas.

Reading is a fast and cheap way to encounter different ideas and mindsets. It’s magical that you can instantly access the thoughts of someone on the other side of the world, or from hundreds of years ago.

At the start of my month I asked my friends for book recommendations, and downloaded the free sample of every single one to my kindle. Throughout the month new people I met continually recommended other books, and I downloaded the free samples for all of them. Then during idle time and before sleep I’d read a part of a sample. This quickly cascaded into a thrilling literary journey, across diverse fields that I normally don’t encounter. New books I read would lead to conversations about them, and then more recommendations. Some of the books I followed into purchasing the full copy and reading, others just lent some direction along the way.

Here’s some books I enjoyed recently, in case they appeal to you. I’ve roughly grouped them by subject.

Meditation / spirituality

• The Baghavad Gita: A classic Indian text on enlightenment
• The Finders: A scientific study of individuals experiencing forms of enlightenment (which they give a tangible definition of)
• How to change your mind: The history and present of psychedelic drugs and their benefits
• The unteathered mind: A rallying call to free yourself from the inner voice
• The universe has your back: Cultivating a mindset of positivity, abundance and opportunity
• Buddhism without beliefs: The tools that Buddhism offers for happiness, removed from religiosity
• The Power of Now: The value of being present

Life advice / romance / grief / biography

• Tiny beautiful things: Cheryl Strayed hard-hitting advice column
• The year of magical thinking: A Pulitzer prize winning account of losing a husband
• Educated: A memoir of growing up in an anti-education anti-medicine fundamentalist household
• Attached: A model of how humans emotionally attach to each-other, and when that can create conflict
• If the Buddha Dated: A fun look at applying Buddhist principles to dating

Assorted topics of the world

• The war on normal people: The structural problems in America’s economy and employment
• A place of my own: A writer’s account of building their own house
• Enlightenment now: Data that the world is in a good plae
• The omnivore’s dilemma: What to eat, and why
• The lessons of history: A pithy review of two historian’s learnings from writing long history books
• AI Superpowers: China, Silicon Valley and the New World Order: Where AI seems to be going and it’s affect on geopolitics
• Pandaemonium: Writings from the industrial revolution
• Sapiens: How and why humans came to be this way
• Utopia for realists

Startups

• The lean startup: A startup is a vehicle for learning and testing hypotheses
• Four steps to Epiphany: A more detailed look at the above
• Blitzscaling: A theory of how capital-rich startups compete
• The Monk and the Riddle: Philosophical reflections on the why of starting a company
• Company of one: Fewer employees means fewer problems. Putting the lifestyle back into business.
• The score takes care of itself: The benefits of running an organization with a strong focus on excellence
• Extreme Ownership: How U.S. Navy SEALs Lead and Win
• Running lean: Iterate from Plan A to a plan that works
• Jab Jab Jab, Right Hook: How to tell your story in a noisy social world
• Grit: The power of passion and perseverence

Travel

During this period I travelled on a couple of weekends to stay with friends. I found changing location really refreshing. Seeing my friends’ lives made it easy to imagine a different version of my life, and made it clear that a life is possible in these other places, doing other things. It was also a pleasant way to recharge from the work of the week.

The process

With all those tools in place, I can now take you through the process that you’ll follow. This is a very self-driven process, the small number of “worksheets” are prompts for you to reflect and capture progress. This is ultimately your adventure, and you have to take the steps forward and choose which signposts to follow.

If you’re feeling the urge to rush forward to see what work is to be done, I’d like to highlight the importance of all the tools in the previous section. They’re all complementary practices to help support an open, creative and curious mind. They are about being able to see more possibilities, and this section is about the manual work of generating, cataloguing, exploring and finally filtering opportunities.

Much like the popular agile engineering approach, this is not a linear process. Instead, it’s a process of iterative cycles of gathering, evaluating, reflecting, maybe changing your mind, and returning to do it all again.

Similar to an early startup, progress is measured in learning, not in getting to the final answers. This is a non-linear process, and if you’re simply focussed on the end-point then going to the start of another cycle can feel like a setback. It’s not, it’s totally normal and expected.

You should expect to over time clarify your answers. You can slowly rule things out, and move other things to the top of the list.

How you’ll spend your time

You’ll spend your time doing three main activities:

1. Desk research (e.g. looking through lists of companies to see if they interest you, emailing people, applying for things, setting up meetings)
2. Getting out and talking to people (e.g. meetings with people you think will have interesting perspectives, interviews, talking to friends)
3. Reflecting and refreshing (e.g. a lot of the tools from the previous section: meditation, yoga, self care, nature)

Ideally, cycle through these things many times. Each of them shifts your knowledge and feeds into the other activities. You want to find insights by repeatedly injecting some new thoughts, letting everything move around a bit, then letting it settle.

It’s OK during this process to change your mind. That’s part of the goal! If you schedule an interview with someone, then a week later realize you don’t want to work in that role, that’s good step forward. You can cancel the interview, or be honest with the team and see if there are other opportunities that align with what you’re now looking for.

1. Desk research

The big questions

Throughout this process you’ll try to answer a bunch of questions. You’ll put down your rough answers, take some time to gather new information, then review them again.

Think of this as an inventory of your beliefs and knowledge. You’ll see what you’re certain about, what you’re less certain about, and see if you get more clarity.

These questions are also helpful prompts for reflection. You may realize that you currently have no answers for some of them. That’s alight, and good for you to know.

Either keep this information in an app you have easy access to, or in a journal you carry around. You want it to be convenient and quick to return to this when you feel like it. I used Apple Notes, where I also journal.

For each of these questions, take a fresh page and be ready to edit it many times. I often made bullet point lists and tables to help structure my thoughts.

The list of questions:

What is your mission for the next five years? What do you want to achieve, what do you want to learn?

This is a really big question, and one that when someone asked me it, I realized to my surprise I had no answer. It’s been really helpful to find some more clarity on this.

What is your superpower? What are your strengths?

Take time to explore what you’re good at. You might have grown a lot since you last focussed on this question (e.g. in school) and the answer might be different. List out the smaller things you’re good at as well as the bigger ones.

Later on, consider whether paths forward play to your strengths or to your weaknesses, and what appeals to you about that.

What roles are you interested in?

Write out a big list of roles you’re interested in. A role could be anything: writer, project manager, parent, CEO, engineer, designer.

Imagine the version of this role that most excites you — what size of organization might it be in, name an industry or problem that appeals to you. Write down your feelings around this. Give this vision of your future an enthusiasm score.

I built this as a table:

What industry/sector/type of problem do you want to work on?

Write out all the industries you can think of into a long list, and score your interest in them. It’s ok to not be sure, you will be refining this list later.

I built this as a table:

Jobs to apply to, projects/companies to start

Depending on if you want to get a job, start a project, start a company, keep lists of ideas for each.

Each of these are a running todo list. Every time you have an idea (e.g. of a job you might want to do), add it down here. If you have a vague idea like “Companies making it easier to manage finances” then add that to the list for later research.

This is a work hopper that you can add to when you have inspiration, then when you’ve a block of time for desk research, you can research / apply / consider some items from the list and check them off.

Learnings

Each time you have some sort of insight, clarity or breakthrough, record it here. It’s helpful to be able to read through these and remind yourself what you’ve learned

Top favourites

This is a summary of everything you’ve been considering. It’s the top five paths forwards, ranked by how much you like them.

Don’t try to fill out all the above at once. You can write down the headings, then come to them repeatedly over time and start to fill them out, then refine them.

Activity: Researching companies and jobs

It’s worthwhile to spend time gathering job/project/company ideas, listing them, then researching them in more detail (capturing this in the tables in the previous section).

For gathering companies, try diverse sources such as:

• Lists of companies in your local area
• Lists of top companies in a given sector
• Venture Capital firms publish lists of their investments, and make interesting lists of companies to browse
• Search for problems you’re interested in and see what companies offer solutions
• Find out who your friends work for and add them to your list to investigate

Get curious! Explore nooks you’d normally pass by.

For gathering jobs:

• Take your list of companies and search their careers pages
• Ask managers directly if they’re hiring, and what they’re looking for
• Send your CV to the catch-all email for companies where you do not see an opening — their current needs might not be reflected in their jobs page, or your skills may inspire them to consider hiring a new role

As you go through all of this, tune into how you really feel about these opportunities. Are you excited? Lethargic? Be honest with yourself, even a good career move is going to be terrible if you’re not excited to do it. If you see patterns in how you feel about different roles or sectors, update those tables.

Activity: Put yourself out there

Unexpected opportunities and ideas will come to you from your extended network. Once you consider all your connections, and then their friends and connections, that’s a huge number of people (for example the average US user has 214 US friends which would equates to ~40,000 friends of friends).

Therefore, spread the word that you are exploring! Try:

• Emailing friends that you’re looking for something new
• Post your CV on community forums, job boards, particularly in places where you have a meaningful connection to the people
• Telling everyone you can (this could include current work colleagues!) that you’re looking

Not everything will illicit much response. That’s normal and totally fine.

Finally, give this some time. Weeks into the process you’ll find friends spoke to their friends, and finally something looped back to you.

2. Getting out and talking to people

Meeting new people has been an amazing part of this process for me. I’ve heard so many of their stories (which are often reassuring — nobody has it all figured out, and everyone’s paths are very irregular) and made a bunch of new friends along the way. I’ve come across many opportunities. It’s been inspiring and encouraging to hear about all the things people are making happen in the world.

I found it really valuable to step into the worlds of all these people, get excited (or perhaps realize I wasn’t excited) about what they’re up to, and see if there was a way I could help. Some meetings became more philosophical, some more practical.

From all of this I learned more about myself. I was asked questions of myself that gave me pause. In hearing what others were doing, I got inspired that I might want to follow a similar path.

On meetings and being an introvert

As an introvert, I often squirm at going and meeting strangers. And pretty much every time I do it I’m glad I did, and benefited in ways I never would have guessed prior.

You need to go out and meet lots of people. You will learn things and find opportunities you would not have otherwise. As humans, we give special priority to face-to-face interactions, paying more attention and offering more help to each-other.

Practicalities

Many of the people I met replied to my post on Work at a YC Startup, a post on a community forum and a bunch came from introductions from friends. A few came from my direct emails to individuals and some from applying to jobs on company’s websites.

Meetings can be as structured or unstructured as feels appropriate.

I found having three focussed meetings per day was pretty exhausting, and I wouldn’t try to schedule more than that.

Things to do:

Talk to your friends

At the risk of stating the obvious, go and meet up with all your friends and chat to them about your lives and such. It’s good to ask for ideas and introductions to people that’d be good to talk to, but you don’t need to push this too hard.

Introductions are gold

Throughout all your meetings, ask for further introductions. If you regularly get enough introductions, you’ll have a limitless stream of vetted, relevant people to talk to.

Organize interviews

Interviewing is stressful but powerful for personal growth. You’ll learn from others what they assess your strengths and weaknesses to be. You’ll also learn how to interview better. Interviews often bring you in contact with the team you’d work with, so you get a deeper feel for what that job would be like.

Go to group events

Going to professional events can be really great. I went to my accelerator’s demo day, and ended up meeting a bunch of new people there (some of whom then made interesting introductions to others). I appreciated having a few friends at the event I knew well so we could explore it together and introduce each-other to others.

3. Reflecting and refreshing

All of the above work is exhausting. Meeting with new people takes a lot of empathy and presence. Desk research is tiring and slightly tedious. Reimagining your future repeatedly is hard work.

It’s important to recognize when you’re having diminishing returns. If you’re tired, you’re not going to have good meetings and valuable reflection. Go and do something else — perhaps go to the gym, or take a walk, or read a book.

Ideas need time to develop

Don’t worry if you don’t straightaway know if a given job or industry is for you. Let it sit for a few days, and come back to it and see what your feelings are around it. As you write down your reflections and summaries, leave them for a few days then look back over them with fresh eyes and see if you still agree.

Shower thoughts and eureka moments

Giving yourself time away from the questions is really important for creativity and fresh thinking. Don’t spend the whole time fretting about figuring out the answers to your future, that’ll exhaust you and rob you of answers. Instead, go find some solitude either indoors or outdoors. Have fun. Maybe hike with a friend, or go stay somewhere new. Let thoughts bubble up, and if you find something good, write it down. Talk things through with a friend and see how you go about telling them what your heart wants to do.

Return to step one

At some point you’re unlikely to make more progress in a vacuum. Start the cycle again and inject some new ideas. Get some new experiences. Talk to some new people.

How do you know when you’re finished?

This is a process of iterative evolution of your beliefs and ideas. You can continue for a set period of time, or continue until you feel a certain degree of clarity that helps you forward.

The process here requires time and effort, so it’s unlikely you want to continue it indefinitely.

I had a set period of time (three weeks fully focussed on this) to do this process. At the end my thoughts of what I wanted to do had changed and sharpened a lot. Enough that I made plans from them of what to do next.

Some of the practices listed in the tools section have persisted with me. I’m meditating more frequently and am more actively directing my mindset.

The leap

At some point at the end of your process, you must translate your insights into actions. There is a tangible difference between feeling you would like to do something and actually doing it. At some point your feelings must translate into conviction.

From hearing the stories of many company founders, it often seems that their conviction grows over time. Initially it’s an oddball idea or experiment, then it starts to work and grows into something bigger. Origin stories often obscure the early uncertainty, implying that the idea was crystal-cut from the start. What I take from this is that it’s ok to be a uncertain. It’s ok to try something out, and see how it goes. You’ll always need to adjust course later.

The ancient adage is apt here: you start a hero’s journey with the first footstep. Whatever you’re considering next, just take one step towards it. Maybe you’ll decide to back off from it. Maybe you’ll dive right in. Either way, it’ll teach you something.

If you enjoyed this I’d love to hear about it. It’s been rewarding to write out this process and I hope that it is helpful. One of the items on my final list was “help other people figure out what to do next”.