Job searching after a break

Maria Lasprilla
6 min readOct 3, 2022


After a short break I am back in the game of working. Did I find a job already?! No, not yet. However, when looking for a job my days fill up in a way that feels like I am already working. Which if you think about, I am. I am working on my next move! And this is a full time effort, my friends.

So how do I approach this transition?

Like anything that starts from zero to one, the energy required is significantly larger than just continuing with my daily inertia. I did not want too much friction when transitioning and quickly drain my freshly restored batteries. That is why I did not set a specific end date to my break but more like a range. I know myself well enough to preempt the need would come organically. And so it did. I started to feel like I wanted to be more purposeful with my days and to work with others. I also knew my husband would be ending his sabbatical soon and home days while friends and family work can feel somewhat empty. During a break I am being useful to myself and my loved ones. That in itself is important. Fundamental, in fact. But once the fundamentals are stable, the next natural thing for me to do is to add a bit more juice to life which I get from working with others in more complex things.

I did have to shift my mindset, though. The desire to be more useful is simply not enough. I have to change gears from being in pure personal investment and recharging mode to seeing myself as an individual part of a larger ecosystem or, as I like to say, as a functional member of society. What’s more, if I really want to be purposeful then I need to increase my chances of ending up in a job I am excited about. Else, my goal of wanting to be useful will fail. So I really have to consider my options.

To start off I set myself a date. Simple. That gives me time to prepare mentally for the action and finish up ongoing personal projects. Having a date also triggers a subconscious kind of work that starts defining what I want. So when the date comes I have more clarity to set some goals thanks to this background work. With goals set I can also put together an execution plan. Having a plan helps me be productive and not just get busy and distracted with every possible job opportunity that comes my way.

The first step in the plan is inwards. It is about setting the criteria of what I look for in a company. Again, this helps me keeping focus when exposed to endless information. It also helps avoid rejecting or accepting opportunities too quickly, without proper consideration. That internal process is a literal long and clarifying conversation with myself (through journaling) where I revisit the things I have enjoyed and have been good at in previous jobs. I also ask where I see myself growing, what topics I have been curious about enough that I am willing to invest time in learning them. And lastly, I profile the kind of environments I have enjoyed being a part of that I would want to join again. If you notice, most of it is based on real past experiences. In my opinion, using hypothetical situations as opposed to reality for this exercise results in setting unrealistic expectations. And we know how virtually impossible is to know what we will want in the future. But we do know what we’ve liked and learned and enjoyed in previous experiences.

The second step is outwards. Since I haven’t been living my sabbatical entirely isolated in a cave, I have conversations to follow up, messages to respond to, events to attend. Having taken the first step is what dictates how I approach these responses. The criteria helps me understand who do I invest time following up with, who do I say no to, and who do I reach out to start a conversation from scratch. This part is the hardest one because just as I have expectations about what I want, companies and teams have them too. There is a strong set of emotions at play here when you know you are being assessed and observed not by one, but by multiple people in multiple teams. So I get comfortable with that vulnerability of being assessed and I manage it by revisiting my experiences, where others and not just myself have considered me impactful and effective, and also which of those experiences I truly enjoyed to the point of being ready to repeat similar ones (hopefully, with a twist). This turns this outwards step into a cycle that reconnects with the first step (my preferences) as I learn about people, teams and companies.

As the conversations move forward or die out, the third step is to revisit my goals. This is not the same as the criteria. The goals help me understand whether I am making progress in my search. The second are about whether in the progress (or lack of) I am finding what I am looking for. One of my goals is having X options meaningfully advanced after a certain period of time in conversations. A small but significant number of successful conversations where only a final decision awaits. That way I can compare and choose what fits my initial criteria best without, again, rejecting or pushing potentially good options for too long, or accepting without proper consideration. I try to make clear at the end of every conversation what is the next step, if there is any. Is it on me or is it on them? I get a date or give one. That way nothing is left to chance. If I don’t get clarity from the other side on a next step or date, I focus on the next candidates and leave the option open but secondary. I also make it clear whether I am interested in continuing or not. Clarity is crucial here.

The last thing, which actually happens early in the reflection, is to prepare myself for the worst case scenario. This is about accepting that I can’t control all the outcomes in this process so I need to decide how I will react when things don’t turn out the way I’d like them to. Things can go wrong in endless ways. I picture some of them, but I also remind myself that there is no way I can visualize all possible scenarios. This is simply a reality check exercise. Wrong can mean that a team I am excited to join decides I am not the best fit for them. Wrong can mean that I’m not excited about any of the options nearing a close deal. Wrong can also mean that I don’t get to my X number of options soon enough and the job of looking for a job starts wearing me down. Wrong could mean an emergency situation appears and I need to put all my conversations on hold. And the world keeps spinning.

It’s been two weeks since I got started I am on step two of my process. My goals have not yet changed. I am advancing conversations and this can take weeks. In some cases even months. So to keep the energy up I balance between the time I dedicate to these and the time I invest in other personal projects. I am also being cautious with how many conversations I hold in parallel. If it’s too little, I may lose confidence if they don’t progress in the right direction, I can also lose momentum if they are too slow. If it’s too many, it’s hard to leave room to process what I’m learning before deciding how to proceed.

All in all, things are going well. I need to stay focused and disciplined, but I also need to chill a little and enjoy the process.

My “job search from home” station. I put the same rigor in job searching as in work itself.

To wrap this post, I leave you with a summary of my process:

  1. I set a date to get started. That kicks off a background mental process without too much pressure to execute.
  2. On the given date, the background process makes it easy to set goals, define the criteria for what I want and I put together a general schedule to follow. This keeps the discipline.
  3. I then start having conversations. This includes existing networks, but also traditional ways. Perhaps following up chats that started in the past. Perhaps saying no. The criteria set on the start up date helps guide the way these conversations evolve. In this step, I make sure to lead with clarity and ask for it.
  4. Revisit goals. Conversations generate new information that may be good feedback for my set goals and criteria. So the process of revisiting goals helps me redefine them or take specific actions with conversations depending on how they align.
  5. And last, I prepare for failure.

Happy Friday,
Maria 🌺

Originally published at on October 3, 2022.



Maria Lasprilla

Product Management, Personal Growth, Leadership. Living The Good Life.