You should know it by now, but I have been an entrepreneur all my life (more about myself here) and I don’t have direct experience of the job hunting process but I’ve been on the other side, hiring and interviewing hundreds of people in my career. When I talk to people about the stress of job hunting, it reminds me of the stress you feel while fundraising for your company or finding buyers for your product.

In both cases you have to deal with a lot of rejection and it’s not always clear where to start. We started raising a fund to build Anthropos at the end of Jan and we recently successfully closed it (more about in the next weeks!). Throughout the process I felt stressed and depressed a few times, especially at times where my process did not seem to work and I thought the all thing was falling apart. It happened to me before, multiple times at Cloud Academy, every time we raised money in fact, and then when I had to sell something, early in my career at HostingTalk and later on for everything we have built.

If there is something that has changed for me in the last 15 years of my career is how I manage my psychology. And even if you are not an entrepreneur, that’s the most important thing you can control in a process like job searching. It completely changes your outcomes, because it changes the way you approach it.

Today I will dive deep on how to manage your psychology while you look for a new job. This should be useful for people that are looking for a new job while being full-time but also to people that have lost their job and need to find one as soon as possible.

Whenever you feel down while looking for a new job, think that this is common and happens to everyone, but most importantly that you will find something that works for you if your persist!

What you are probably experiencing while job searching

A few common experiences if you are job hunting:

  • You don’t know where to start: it might be because you don’t know what you want to do next, or simply because you still need to find something that is truly interesting for you.
  • Depression and lack of clarity: especially after several applications and no answers, you wonder what you are doing wrong and sometimes you lose faith, slowing down your job search or not following your process because “it doesn’t work”.
  • Rejections that don’t make sense to you: this is common, for many job positions it looks like you might be the perfect fit but you don’t get any answer or you get rejected without a proper explanation.
  • Lack of job positions that fit your skills: you can’t find enough positions that match your skills and criteria and feel like what you are looking for doesn’t exist.
  • Loss of momentum once you have tried several different things:you applied to 50+ positions and got nowhere. It’s easy to wonder what would be next and what else you can do.
  • Several interviews and then a rejection: a very common one, they simply decided to go with another candidate.

I can’t tell you how to manage every single situation here, but there are a few things you can try that will improve your approach and will make you feel better even if nothing seems to go right.

Build a plan and stick to it…even when you don’t feel like it

Like in fundraising, build a plan: very often that plan is a spreadsheet where you list job applications – I talked about it as part of building a playbook for job hunting. This is helpful because it helps you with your plan execution. Every day you will reach out to multiple companies, look for new job postings and spend more time on the ones that you like the most.

In my experience this plan will help you even more on those days where your morale is low: you don’t believe you can find a job anymore and you start doing random things. That’s exactly when you need a plan to force yourself to stick to it. Bad day? Open the excel file and start working on it anyway. Trust the process and you will feel better, but most importantly, you will get to the end of it and find success.

I have recently written about job hunting when you have a full time job as well: in this case you will experience something similar sometimes, simply pushing this activity to another day when you are not so tired. Having a plan will help you stick to it.

Put things into perspective: it might take a few months but you will succeed

2023 is probably not the best year to raise money – markets are down and so is venture capital. As I started raising money back in January I had multiple people telling me “good luck, this is going to be hard and you might not be able to raise“. Then I flew to San Francisco the weekend of the Silicon Valley Bank collapse, and I looked at my list of investor meetings wondering why I was even there!

I could have stopped fundraising at that point, but what worked for me was simply understanding that companies were still raising money and I had to accept the fact that it might have taken longer to complete the round but that ultimately I would have succeeded if I kept talking to people and following my process.

Job searching is similar: it will not happen overnight and in a job market like this one, it will be more difficult. The reality is that if you persist and understand that it will take time, you will feel more positive about the process and that’s when things will get better.

Do things that don’t scale and differentiate yourself

This is an evergreen. You must do things that don’t scale while you are looking for a new job. You cannot do that for every single position you apply for, but pick 2-3 positions and spend hours on them, to the point that the person receiving them feels bad not even replying to you.


  1. Research everything about the company and the role – use LinkedIn, read their social media and collect enough information you can spend at each step of the application. It’s easy to drop pieces of information that make the recruiter think “This person really did a lot of research
  2. Build a project for them that talks about what you can do: I talked about it here, with several examples. It takes probably several hours of work in some cases, but it’s the best way to land an interview in my experience.
  3. Reach out to the recruiter and other people responsible for that department or job application: using LinkedIn and several messages that you need to really customize. It works.

This is a ton of work, but once you have done it, you will experience a lot of gratification. You show yourself you can really build something and be helpful for a company and in the process, it will be a good reminder of your skills and your ability to definitely find a job.

Talk to other people and share notes with them

This is something I tend to forget when I face a challenge at work. There is someone that is going through the same. Talk to other people in your shoes or people that have been there. Sometimes we don’t do it just because we fear the potential judgement of others, but that’s nothing compared to the benefits you can get from sharing your experience with others.

If you are job searching try to connect with people that are doing the same and ask them what they are doing and how they are feeling. The same happens among founders: when you are struggling building your company or raising money, there are not many people that can understand you like other founders.

LinkedIn and Reddit are the tools I would use here: on the first one it’s easy to connect with other people looking for a job and grab their mind in a call. On reddit there are many communities (Careerguidance looks like the best one to me so far) where you can ask questions and explain your specific case: my experience reading them in the last months has been particularly good. There are great advices and many people that will spend their time to give you ideas.

Take a pause from your process and focus on other tasks

If you are working on job searching full time, you need pauses from time to time. Every week you can spend a day doing something different: reach out to people in your network and ask them if they know anyone looking for your skills. I know this is not easy but there are many ways to start doing it. Use LinkedIn and start with people you know better, like former colleagues or friends.

They might not have any suggestion for you right now, but they will keep that in mind and they will reach out if they hear anything. The better you communicate what you are looking for the more successful this effort will be because people in your network usually want to help you and you increase your chances of finding a position through them.

Don’t take it personal and don’t overthink feedback

This is interesting for me. When you start your company everything feels a bit personal to you: the venture capitalist that doesn’t invest and gives you 38 reasons why your company might never go anywhere, feels something very personal!

After many years doing it you will simply ignore that and move on, but at the beginning it can easily kill your morale.

The secret here is to ask yourself how they know that. That’s the same for recruiters and companies that reject you: think about the fact that they gave you feedback based on an impression and a small set of data points to judge you. In 90% of cases they might have other internal reasons as well that will never share with you, and the feedback you have heard was just an excuse. I could continue forever: I’ve seen this many times while interviewing people. While I always asked our HR team to give people real and constructive feedback, I know that many times we simply failed and ended up giving people useless feedback that had nothing to do with their interview and skills.

My suggestion is to not overthink feedback you receive from companies and recruiters. If you really want to get more in some cases, ask them “do you have 5 min to tell me more?” – great recruiters will accept and that’s your occasion to dive deep and find learnings there. If they don’t accept, move on and just focus on the next company!

This is it about managing your psychology while job hunting. Comments are open and I would love to hear more ideas about it.

If I can help my calendar is open: I am taking a few calls every week to help people review their resume and applications for free. If you think I can help or you simply feel a bit stressed by the job hunting process, book 30 min.

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This blog wants to help you understanding how to improve your career, acquire new skills, move to new industries and in general, how to deal with your job and think about it in your career context.

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