Just a few months ago I made the decision to move on from 6 1/2 years at a large, successful software company, Atlassian, to join a small Australian startup called Qwilr. At the time it got some attention, and some curiosity, on why I’d make such a move.
It was indeed a really hard decision, requiring a lot of “head time” and “heart time” to work through. I was historically a “head guy”, applying the usual pros and cons approach to decision making. While I did do that, here I’d rather share some of the newer (to me) “heart tips” for working through this kind of big decision.
Know your season and make a change
I’ve come to believe in two energising seasons in one’s career: Learning and giving.
Learning doesn’t just occur early in your career. A number of years into mine I found myself in a bit of a rut, but I didn’t feel it was the right time to change companies or my role. Deep down I believed I had more to learn. I decided to throw myself into reading, and read approximately 40 business and self development books over a period of about 2 years. That gave me purpose. When my next opportunity, and therefore season, came, I was ready. I still benefit from what I learned then.
At other times. it’s clear that you are giving. You are applying one or more of your strengths for the benefit of others around you, maybe in leadership or maybe just making an impact. This gives tremendous energy and you feel the impact and utilisation of your gifts and abilities.
Sometimes you find yourself in a stretch season, learning and giving as you step up to a new responsibility that is on the fringe of your abilities. In this season one can feel anxious and suffer a form of Imposter syndrome (shoutout to my former CEO). For others, it can energise them. For large stretches of my time at Atlassian, it was a bit of both!
If you are in a position where you are neither learning nor giving, you are likely to be feeling low in energy and generally, in a rut. I’ve jokingly called this the “Composter syndrome”… To that, I say: Can you find a new season where you are, or is it time for a bigger change in your career to unlock your next season?
Define your passion and step towards it
I have spoken with those trying to decide if they want to be a leader or become a more senior technologist. One question I tend to ask them is: If you had to choose between helping someone grow and making an amazing technical achievement, which would you choose? You may say both, and I can relate to that However, just for the exercise, choose one. Is what you are doing leading you in that direction? Regardless of your actual responsibility, are you able to lean into this impact (e.g. mentoring peers)?
It can be easy to give your all to your organisation. You believe in their mission. You love their culture. However one day you wake up and realise that you have been fulfilling their goals for so long you have forgotten about your own. Rediscover your passion, the change you want to see in the world! I remember the time years ago when I realised that my passion was in the growth of people and multiplied impact that a team can achieve. It meant I made decisions that sacrificed technical achievement to gain the necessary skills and experience to grow in my ability as a leader. It took some time to reach my destination but I did and it started with that choice. More recently I was reminded of my passion for building teams and creating a diverse Australian tech industry. I feel grateful that I’ve had the opportunity to chase those passions.
It’s not a zero-sum game. The best employer/employee relationships give to both the organisation and the individual. The individual is ideally doing “the best work of their lives” and are therefore making significant contributions to the organisation’s success while progressing their personal journey.
Whether it’s just a conversation or a bigger change required, what is the next step in your life or career passion?
Spend heart-time in the future
Let’s say you are considering making a change. Are anxious about whether it’s the right one? Maybe your head tells you it’s the right next step, but your heart is struggling for various reasons. A strategy I’ve more recently learned in this situation is to “spend time in the future”.
Let’s say, hypothetically, you are considering leaving a large successful organisation and joining a small startup. How can you know if you will adjust to that different environment? Maybe on the face of it, the skills are there, but you sense so many unknowns. Doing highly analytical pros and cons exercises is fine and good, however, that doesn’t make you worry less about the change.
Try spending some “heart time” by pretending that you are in that future role. When you wake up, imagine that you are going to that place to work instead of the one you are still at. At the same time, see if you can let go of a bit of what you’re doing now for a day and see how that feels. You sense the buzz of a large number of people fading, and yet they are replaced with more intimate working relationships in a tight-knit organisation… Do you find yourself mentally and emotionally transitioning? That’s a good sign. We’re not always good at knowing what is the next right thing to do, but this trick can really help us find more clarity at a deeper level.
For me, this meant my last career transition has been the smoothest one yet in terms of adjustment. What is the future you need to spend some “heart-time” in?
Write the narrative for your next step
Similar to heart-time, this is another trick for seeing if a particular decision works for you. Imagine you’re being interviewed a month into this new role. The reporter asks you “so why did you leave Atlassian for an Australian Series A startup? Why didn’t you go to the US or a larger tech company which is what others in your position typically do?” What is your answer to that? I actually was asked this in my recent move, and I explained that it was a combination of wanting to make an outsized impact by drawing from all my skills that I’d built over time, that it was time for me to contribute to the growing Australian tech ecosystem - to “walk the talk” of my advisory relationships, and the company I was joining shared my values in creating teams based on a strong applied IRL culture.
Try this as an exercise. Whether to new company X, to start your own business, to change your career direction, to join that big-name knowing you’ll be a “smaller fish in a bigger pond” or whatever else it is, why are you considering moving? Try to write that news article that explains it. Be authentic, and it will be more helpful. If it rings true and motivates you more strongly towards actioning that narrative, that’s a sign you’re heading in the right direction.
One more thing: The story doesn’t end with your next step. You’re just writing the next chapter. You may have in mind a chapter after that. That only means you need to more strongly get to the next one to keep up with the plot!
Find your tribe
Last but not least, you need to find your tribe, i.e. the group you feel a sense of belonging to. I loved Atlassian’s values and the way they were applied. They were spoken of, used in decision making and lived out in collaboration and getting work done. I had found my tribe.
Considering a change, I wondered if I could exist outside of that culture. About 18 months ago I did engage in a few exploratory conversations. I heard statements like “we don’t have values, we have standards”, “what’s your favourite book” (which on the face of it is fine except when there’s a “right answer”) and “the best decision for you to make is to join us”. If someone is evaluating you, don’t forget to evaluate them, and pay attention to the vibes you take away!
After a serendipitous connection with the founders of Qwilr, and during our subsequent exploration, I realised how compatible we were. The reality is a strong match. I have again found my tribe. It was still a very emotional time for me to say goodbye to my last tribe, and I was very lucky to have some close supportive friends that reminded me that my tribe would extend beyond the walls of organisations. It was the truth.
If you don’t feel that where you are is your tribe, you may not be aware of just how important this is. If you are aware but are still considering making a change, describe what “your tribe” would look like. If you are exploring, ask yourself “can I call them my tribe?”
Closing thoughts
I am grateful for my career to date. I’ve had many roles in technology companies making a global impact and have met some amazing people along the way. I’ve been through several seasons of learning and giving and times when I have been more or less in pursuit of my passion. There were many decisions along the way and when I sit down and think about those I’m proud of some moments and shake my head at others.
On this note, my letter to my 19-year-old self coming out of university would read: “Ben, you make a lot of decisions with your head, but you will need to learn also how to make decisions with your heart. Start thinking about that now rather than in a few years time. It will serve you well. …. P.S. don’t give up Basketball!“
Are you considering a big decision and are struggling to reconcile your head and your heart, or are just finding yourself in a rut and don’t know why? These could be the very practices that give you the courage to face that big next step.