Traversing The Transition

I just returned from a marvellous Global Summit organised by the Sandbox network, a mobile society of entrepreneurs, journalists, academics, politicians, and influencers from over 100 countries, using technology and conversation to create a world of our design, and we were on a private island resort in Croatia spending time talking about life, personal development, relationships and of course — transitions.

The network is in that state of transition. We have come through a 3-year period of figuring out what we as a network would move forward as, with new leadership and maybe even new ways of governance and financing. Part of the Summit involved some key volunteers in Sandbox coming together to discuss the next steps, and the topic of transitioning was the dominant topic. One of the facilitators of the discussion, Per Jonsson, spoke about transitions in closed doors and open doors, and more notably expanded the analogy to include the corridor in between these doors — and it is on this corridor that my thoughts dwelt most.

In life there are closed doors and open doors. When you decide to leave a room; a phase; a stage of life, you close the door behind you. But before you reach your next door, there are so many questions: What door is right for me? Can I open these doors myself? What if there are no doors open? Do I walk on or do I wait for the door to open? All these questions have one similarity: They occur in the corridor.

This corridor is a frightening place. It’s a place of uncertainty, of no control, of fear and of instability. But it can be a wonderful place of reflection, retrospection, discovery, and even release. Coming from a transition period myself, I identified with the situation Sandbox found itself in.

The beautiful island of Obonjan gave me time to mull over what it meant to be in the corridor — and more importantly, what it takes to cross the corridor well.

1. Rest

A common factor between people who are in transition is unsurprisingly the need for some recuperation. The tricky thing is that we don’t know it until we actually get some rest. We push our bodies to extremes — overloading on caffeine and alcohol, allowing ourselves an average of ≤4 hours a night for sleep, occupying our minds with stress even during off-work hours, you name it. But we also adapt well, and that means we numb ourselves to the damage we do to our bodies. So when we finally break away from that, the weight of damage comes crashing down when our bodies stop releasing the adrenaline we’ve allowed ourselves to run on for so long.

The first thing I found useful was to enter a transition state of mind. Recognise that you are in transition, that you have closed the door of the last phase behind you, and you will be moving forward. This state of mind will ready yourself for the very different steps that you have ahead of you, and they cannot happen if you are still stuck in the previous phase mentally.

Your surrounding environment will also be extremely noisy — people will ask questions, strangers will judge, your family will be concerned — but for your sanity’s sake, your resting has to involve shutting out the noise to enter a safe mental space. Find your isolation corner. Sit in silence. Get in touch with your inner self; your spirit. It is astounding what 20 minutes of peace can do for the next 20 hours. Make this a habit (I’ll share more about habits later) and you will be amazed at the clarity you gain when you do this.

Over time, make it a point to listen hard to your body and be aware. You will realise some very tangible changes in your body and wellness: You sleep better. You eat better, picking up healthier eating habits. Your energy feels revitalised. You feel happier. This is when you know you’ve entered a good place — one where it’s almost like your body and mind are telling you: “We’re ready for what comes next.”

2. Structure

Being in a transition state, there are effectively no rules that you abide by. No fixed working hours. No lunch hour. No office space. While that lack of structure was initially scary, it can be liberating — and very quickly. The boundary-less life gives you flexibility; gives you freedom. And yet, this is actually one of the potholes of the transition road. It’s a trap that ensnares you into a freestyle motion, and threatens to derail your next steps if you’re not careful. Because of this, it is important to recognise this possible fall and actively create barriers to the tempting comfort of staying in the boundary-less lifestyle.

Treat the transition period as what it is: A period. There must be an end goal, and the end goal must have a due date. If this was a job, what is your last day? What would you have achieved by this day? What can lead you to the week after this specified last day? In essence, set your final achievable outcome and date of delivery. This doesn’t have to be specific to finding a job. It can be a skill you want to pick up, a book you want to write, or a gig you want to pursue.

After you’ve done this, it leads into breaking down your final achievable outcome into monthly and weekly self-checkins. What are self-checkins? They are moments when you track your progress towards your end goal. This is done in milestone tracking, adjusting your weekly action plan according to how close you are to the end goal. This is your only function of accountability to yourself, and this can be a valuable measure of how disciplined you are. I personally have a dual purpose for this: To keep myself in check, and to hone my own discipline.

Habits are extremely useful in ensuring you maintain a structure. These can be anything: From waking up at the same time every morning, to writing a blogpost every week. Adopt small habits that can remind you of a work day — enough to keep you disciplined but unhindered. Feel free to make these fun (but healthy) habits too, like going for a casual bike ride every evening, or spending an hour every day to read. Just make sure they are kept to, and they make you a better person at the end of the day.

3. Be Accountable

Part of the freedom that the transition state gives you is the liberation from having to report to people. There is no more boss supervising you, there are no more ‘peer leaders’, and there is no more team to serve. Similar to the above argument on structure, this liberation can be a trap. Reporting to no one is a common arrangement in the digital age — we have more freelancers than ever before, the ‘gig economy’ favours the explosion of short-term projects, and a digital nomadic lifestyle has an allure boosted by the likes of Instagram and Snap. And yet, running seemingly counter-intuitive to the nomadic lifestyle, we find that the most successful remote workers maintain a sense of accountability.

It becomes increasingly important for a professional to be tethered to someone else, lest they carried away by the freedom to decide one’s own outcomes. The question is: Who is that someone else? Is it one person, or is it a collection of people? The first step to making sure you’re not just giving yourself excuses is to find a support system. At Sandbox, many of us hold each other accountable as we share about our life goals and aims. Some people have close family members as their support system. Some have childhood friends, or ex-colleagues. The only criteria for this support system is a full wholehearted trust in that person, a willingness to be raw and vulnerable, and a fearless forthcoming approach that is not hindered by fear of judgement, competition, or reprimand.

Something I personally found difficult was to have 100% trust. It took me a while to register that these people whom I want as my support system already see my flaws as clear a day before I even try to hide them. Some others I’ve met found it difficult to be wholly forthcoming, fearing a negative impression. If you have any reservations, it’s important to overcome them on a personal level first, or it will be difficult for any support system to provide that feedback you need; that feedback some call ‘real talk’.

This feedback is so absolutely crucial to one’s personal development in the transition stage that to not have access to it, or worse, to hear it but not listen, can have lasting damage on one’s next steps. Always remember that you chose these people to be vulnerable to, and they agreed in one way or another. Take the feedback to heart, and ponder their point of view even if you disagree with it immediately. There is merit to agreement — it is validation for your thoughts — and there is merit to disagreement — it is an intellectual and emotive challenge to your opinions. Debate healthily, without anger or spite, and constantly remind yourself that you are a team working towards one outcome: A better you.

4. Redefine Search

After you’ve rested, maintained your performance through structure and accountability, you finally search for your next step. This is where most people jump right into without waiting. They miss the first three steps, and many of them find themselves in yet another bad (or unsuitable) role, or just realise that they’ve carried the burnout with them as they walk through their new door. If you haven’t done any of the above three steps, please do yourself a favour and implement them first. If you have, this is where things get exciting. You feel like a kid in a candy store; a child in Disneyland, there is just so much to do and so many new shiny things to rush for and you don’t know where to start. The big (and frightening) difference is: Once you make your pick, there is no turning back.

Most people I talk to who are in transition or want to quit their jobs don’t actually know what they are searching for. On the flipside, those who know what they are searching for have a very clear defined path to discovering their next step and why they would be searching for that. I think it synthesises into three simple questions:

1. What is your personal desire?
2. What do you need in this current stage of life?
3. What makes you a better person?

When asking what your personal desire is, it is not about the fluff answer that you give an interviewer. It is what you tell yourself when you look at job postings, and what you dream of in that moment just before you head into slumber. Is it a prestigious title? Is it a corner office? Is it Google-like perks? These personal desires aren’t shameful, but they can be a barrier if you’re not careful. Learn to accept them, that you will be subconsciously biased against a job opportunity that might be really attractive save for that one desire it doesn’t fulfill.

Your needs are probably the most pressing factor that you’re in the search for. These are practical needs: Money for rent and bills, stability for the family, gainful employment for the right to stay where you are. Make a list of all the pragmatic concerns you have and use these as a criteria to shortlist opportunities, dividing between the shiny and the useful.

If you’re in the beginning of your career, or are relatively young, the most important factor is probably your growth trajectory. Your search must involve future-planning, thinking about the person and worker you are in the next 5–10 years. What role will help you hone the skills you need for your next step in your career? Is a career shift needed for that to happen?

The sweet spot is surely the role that appears in the center of these three factors, but don’t be confined to this sweet spot alone. Few people find this, especially when you’re in the first 5 years of your career, so set up a ranking/weightage system that allows you quantify the value of the roles available to you, and make your decision accordingly.

5. Burn No Bridges

Every phase of life stays with you, even the ones you leave behind. How you depart is how you will be remembered, and the legacy you leave will turn your work into a stepping stone or into a prison ball-and-chain. More than just leaving a good impression for a glowing reference letter, it is paramount that you recognise the value of relationships in an ever-connected world. Opinions are shared freely, whether over drinks in a bar or over DMs on Twitter. Stories are exchanged both openly and in secret, and more often than not you find your past coming back to either elevate you, or haunt you.

Easiest to maintain are the relationships you have with your former co-workers. These people have spent the most time with you in the past years, and have the best insights on who you are as a worker. These insights can only serve to benefit you, should you take them into your learning process. Similar to being in the office, multiple levels of relationship management must be observed: An upward management of your former supervisor and how you can maintain the learning you’ve been receiving from them, a downward management of your constituents and how you can continue providing the genuine support for their career paths, and a lateral management of peers and how you can keep each other accountable for the growth trajectories you are on. It sounds like hard work, and it actually is. But it can be done if you make a conscious effort to build it. Relationships require working on, and you’ve been doing it for the past years. There is no reason to let it go in a snap.

What is commonly neglected is the relationship you might have with your potential hirers. This may be the relationship built with a senior level person, or with a team of people, given that the hiring process has now evolved to include ‘culture tests’ where you spend some time with the people you might be working with. Naturally, as you can only pick one, the opportunities which you don’t pick are left abandoned. But that does not mean the relationship should be too. It holds merit to offer a hand to connect with the people you met and once considered working with, and allow them to feel like human beings who had something with you, rather than as pawns who were pieces in a bigger game of ‘Pick Me’.

Choosing The Door

Making that leap is never an easy step. You’re basically choosing what you will be doing for the next 2–10 years, possibly affecting the path you will take for the rest of your life. But don’t be in a hurry to make that leap. Doors come and go, some open and close in (quite literally) minutes, some remain open for months. There will always be pros and cons in choosing which door to walk through. But what is necessary to understand is that you need to spend enough time in the corridor — and what you do while in the corridor will influence your actions as you approach your chosen door.

Coming from the Sandbox Global Summit in Obonjan allowed me to synthesise the thoughts I’ve had while being in this transition stage, but more than that it also allowed me to connect with inspiring individuals who have also spent a lot of time thinking about transitions and how one might manoeuvre this tricky point of life that doesn’t yet have a ‘guidebook’ the way career coaching does. Leading the charge is Fabian Pfortmüller, co-founder of Sandbox, and he writes extensively (and collects fellow Sandboxer’s thoughts) about transition on transitionnotes.com. Transitions are subjective, exciting, scary, revitalising, uncertain. and so much more. But more than ever before, transitions are an opportunity to truly discover what one’s intention is in the life we lead. We live in a time where we have a roof over our heads, power for our machines, and network connectivity for me to write and for you to read this — let’s take advantage of this to make transitions more productive and positive for generations after.

(Timothy Low is an experienced trainer, founder, and project manager. He founded a training consultancy focusing on bespoke leadership programmes, social cause hackathons and design thinking before joining Singapore’s largest L&D company as Entrepreneur-in-Residence. He most recently was Programme Manager for Entrepreneur First, a pre-seed company builder from London. Tim is also an Ambassador for Sandbox Singapore hub, a member at Kairos Society ASEAN, and volunteers as a Community Lead with Singapore+Acumen. This post first appeared on timothylow.com/blog.)