From Entrepreneur to Product Manager. Why? How?

Most of the time when people think about becoming an entrepreneur they are doing it from the employee position. Usually they have some (more or less) working experience in a company and they want to apply this experience to their own business. I think this is the common situation, with fewer cases when a student is starting his/her own business directly from the school years or immediately after graduation, with zero experience as an employee.

Sometimes the reason is frustration – they feel limited (by company policy, by their boss or whatever) and they think they can do a better job for themselves. Sometimes they just have tons of ideas and they didn’t find the proper terrain for transforming them into reality because their daily job is too demanding or company policy is not allowing side-projects. Sometimes they just need to feel free. And sometimes – not so common as it might seem – they are doing it for more (hoped!) money.

Whatever the reason is, one thing is sure: many of the employees find the idea of running their own business one day, very appealing. Most of them will never make it because the comfort zone given by a stable income is the biggest enemy of making the step to entrepreneurship. The bigger your current salary is, the smaller chances are you will give it up and take the risk of starting your own business/startup. But as I said, entrepreneurship is “the secret dream” of any employee. What about the other way round?

Why switch (back) from entrepreneur to employee?

Even if it seems uncommon, switching back from an entrepreneur career to employee is happening. And I am not even sure if this is so uncommon as it might seem. And of course the first reason you might think of it is failure, and it really could be, but there are many other possible reasons. 

Mark Zuckerberg's Business Card

Mark Zuckerberg’s Business Card

When you are running your own startup, most of the time you have to wear multiple hats and change them daily. Being the Product Manager, the Lead Developer, Chief Financial Officer and also clean the floors every Friday evening it’s not for everyone. And doing this for long enough can be equally – for some even more – frustrating than work in corporate, executing on someone else’s strategy. 

Running a startup is never easy. Forget about the fixed, predictable schedule and forget about the two weeks holidays on the Greek islands, unless you want to spend it on the phone with your employees and customers or responding to emails and solving different conflicts from distance. Try it once and you will never want to repeat the experience. Having a family is even harder. Less time to spend with your children, less time for your partner, more frustration. Family can be a good (and perfectly understandable) reason for quitting an entrepreneur life and going back to employment. Sometimes when the partner is losing their job and the only stable income for the family is gone, you just can’t continue investing your time and money in a startup that doesn’t pays back yet.

Another reason for quitting entrepreneurship life can be higher expectations. Even if your business is working, it pays all the expenses, salaries and maybe even makes a small profit, it could not raise to your expectations. Especially when you are into the business for few years. Market conditions can change, and most of the time it does. Your niche is too tight and there is no room for more. Or you just feel you reached a plateau and you need to make an exit.

And – let’s face it! – succeeding as an entrepreneur it’s a difficult task. 9 out of 10 startups are failing.

There are tons of reasons why and we are not going to discuss them. And all the people working for failing startups must find new jobs, including their founders.

How to get back to a “regular” job after being an entrepreneur?

The way you get back to the employee status after an entrepreneurship career it depends mostly on the reason you are leaving it and your future plans. Was it a failure and you just need to recover before trying again? Your life conditions (family, health, etc.) changed and the entrepreneur life style doesn’t fit you anymore? You felt limited by resources and you wanna try to succeed on a bigger scale?

You need to step back for a while and be brutally honest to yourself. Why am I stopping? What am I hoping for in the near and not so near future?

If you failed and all you need is some cash before trying again, and you already have a plan in your mind for the re-launch, then please, try not to contribute to other’s failure. Yes, an employee is not a company property and you cannot and shouldn’t try to force them stay. But if you just know from the very beginning you will not stay for long enough in a company, then try not to cause them troubles. You were in the position where you had to hire people and you know how hard and time consuming this process is. Plus the adaptation time before they are really starting to be productive. Try to find project-based jobs and make sure you stay committed to the project till its completion. Try to find consultant jobs and just try not to be an asshole. 

If you are planning to stay, then be honest to your future employers and let them know the real reason you are getting back to employee status after an entrepreneur career. Remember how it was when you hired people and act like you expected them to act when they showed up for an interview. I bet you wished they’d be honest and with transparent intentions. Be like that. They will appreciate it.

Find the right role!

Like I said before, the entrepreneur position forced you to wear many hats and you did it, whether you liked it or not. Take your time to think of all the tasks you were doing back then and try to remember how you felt when you did it. What did you like to do most? What was a real chore? And, more important: what did you do best? Where did you excel at? Then define the role you would like to play in a company based on the answers to these questions.

Don’t be intimidated if you discover you don’t have a diploma for that role. Remember: a piece o paper is many times useless or less important than good experience hardened in trenches. Always get back to the time when you were looking for good employees of your own: what would you have preferred?

After you found that “perfect fit” role for the future you, based on your experience, review your CV. Instead of just being the CEO of startup X or Y, highlight those aspects of the actual job you have performed. You want to get back to coding? Then try to emphasis the coding tasks and – more important! – the achievements you have reached as a software engineer in your startups. You felt you were an excellent business analyst? Highlight that! Was product management your passion and you feel like you should concentrate on that that for the next years? Highlight the achievements and responsibilities you had that fit into a Product Manager job description

Look for jobs you are targeting and read very carefully the “Responsibilities” and “Requirements” sections of the postings. Check all the items you performed before in your entrepreneur career and be honest to yourself. How often you did that before? How well? Did you love doing it? Would you do it again? Define a checkbox for each line of the responsibilities section and check all you did before. If you see a lot of them checked, then – Bingo! – that’s it! Concentrate on that position! Review all unchecked boxes and try to understand what is all about. What does it mean? Is it somehow similar with any of your previous experience? How fast can you learn that? And start digging the subject.

Take your time to dig into the job description, read about the subject, learn about it and see how fast you are making progress. Start with the things you consider more difficult and see if you feel passion and desire to learn more or if it’s a pain. If you don’t like it now, when you don’t have to do it, how will it be when you will have to? 

Get over the “impostor syndrome”!

Yes, that’s right. The impostor syndrome exists and it’s possible for you to get through it as you end your entrepreneurship journey and look to get back to an employee role. Mostly if you target a role that you didn’t officially performed before.

Impostor syndrome (also known as impostor phenomenon, impostorism, fraud syndrome or the impostor experience) is a psychological pattern in which an individual doubts their accomplishments and has a persistent internalized fear of being exposed as a “fraud”. Despite external evidence of their competence, those experiencing this phenomenon remain convinced that they are frauds, and do not deserve all they have achieved. Individuals with impostorism incorrectly attribute their success to luck, or as a result of deceiving others into thinking they are more intelligent than they perceive themselves to be. While early research focused on the prevalence among high-achieving women, impostor syndrome has been recognized to affect both men and women equally.

Keeping or building self-esteem in your situation can be challenging. Even if you performed all or the majority of the tasks described in the job description, you still might feel like an “impostor” because there was no official title given to you by an organization. You didn’t have a business card with that role printed on.

Frankly speaking, we all know some people with fancy titles working for big corporations and all they really know how to do well is to sell themselves as good professionals. If you ever worked in a big organization you probably know what I am talking about. It’s that guy that shows up to all company meetings, actually prefers them to the actual work, and try to impress anyone, especially his superiors. Still everyone is whispering: what is this guy actually doing in our company?

Well, you’re not that guy! You put a lot of sweat, time and hard working in doing things while you had nobody around to praise you and to give you titles and promotion. The praises and rewards you got were customer satisfaction and the happy team around you.

If you are doing it, stop disregard yourself and compare to others, especially with the image of others you are seeing on LinkedIn, Facebook or other places. The startup failures you had are not defining you! You had the courage to start it and you should have the courage to admit you failed and get over it.

Think of your strengths and highlight them!

Being an entrepreneur requires a lot of courage. There are not so many people who are risking their warm seat in a company to start their own startup. And yes, you are one of them, one of the few. You did it and no matter how it ended, you had the courage to do it and now you have the courage to get back.

Being an entrepreneur requires a lot of hard work. And you were not afraid of willing to do it, and you actually did it. You were there when your business need it, no matter if it was Sunday or sometimes middle of the night. You just knew you had to fix the problem and you did whatever it took to fix it.

Being an entrepreneur requires a lot of passion and confidence. Passion was probably the main reason which determined you to quit your stable job and start working on that special product you conceived, designed and built. You believed in your product and you did your best to make it the best. You were confident with the knowledge that will make your businesses succeed. You worked to build the right product and to build it right! 

Being an entrepreneur requires a lot of discipline. There is nobody out there to tell you to finish your tasks or not to leave the office at 5 PM because there is an emergency and you need to take care of it. There is nobody to warn you are spending too much and you can live without that nice to have “X” in order to get the more important “Y”. You have to figure it out by yourself, and that’s requiring a lot of self-discipline.

Being an entrepreneur requires agility. With very few exceptions, the initial plan never stays the same and it’s not a rare situation when a pivotal move should be done. And being agile so you can quickly adapt is an important skill to have. As an entrepreneur you have to always adapt the business/product to the market conditions and you have to adapt yourself to the required tasks you have to complete. You have to use empiricism to build, inspect and adapt all the time. And even without noticing you are applying agile and lean concepts, you are applying SCRUM and other techniques you maybe didn’t know about. You did it because you used your logic and common sense to increase the value of your product and sometimes just to survive.

Being an entrepreneur requires initiative, ability to prioritize and sometimes the courage to say no. There is no doubt you have initiatives. It’s actually why you started your journey. And with limited resources, no matter how many ideas and initiatives you have, you must be able to prioritize and if the list of “todos” becomes too big, you just have to say no. 

All these are qualities that every smart employer is searching for.  These, plus the confidence, open mind, creativity, determination and many others. And if there is a situation of crisis guess who they’d like to have around: the guy with the fancy titles who’s showing up to every single corporate event and speaks “from the books” or the guy who had to solve by his own a similar situation before?

Do you have a solid entrepreneurship background and (for whatever reason) you return to the “employee condition”? Consider working as a Product Manager!

My favorite definition of the Product Manger role is this: “A Product Manager is responsible for building the right product and to build it right“. Despite being such a versatile role, I think this short definition manages to cover the essential. Even if you didn’t know too much about product management before, the good news is you just only thought you didn’t know.

If you were an entrepreneur running your own startups for few years, you were actually acting as a Product Manager. You most likely took care of the product strategy, you had a vision for your product, you analyzed the market and the competition and you probably tried to differentiate yourself from them. And you most likely had goals and initiatives for reaching these goals guided by a roadmap built and released product increments, day by day, developing features from a prioritized list. You collaborate closely to other people from different other domains: your accounting expert, legal services and maybe marketing guys. You were probably applying different methodologies abbreviated with letters you didn’t know even exists.

Be self confident and don’t stop learning!

When you start digging into the theory of every domain – software development being my first thought – you may find yourself overwhelmed by all this terminology, concepts, frameworks, theories and techniques. You don’t have to! Don’t try to look like an “expert”. Frankly, by definition, you are not even one.

But you don’t have to be an expert. Smart companies don’t necessary need experts. They need problem solvers. Because their customers don’t care who’s doing the job. They need products they love, products that brings them value, built by people who understand their needs. And as an ex-entrepreneur you are one of these people.

But don’t fall into the opposite side: just because you were an entrepreneur you don’t know everything and you can’t solve anything by yourself. Never stop learning, never stop being better today than yesterday. And if you do this, there is no need for you to worry. And if any company is not hiring you, not because they have doubts you are a good fit, but because they think at some point you will start your own journey again, think of this famous anonymous dialog:

CFO: “What happens if we invest in developing our people and they leave?
CEO: “What happens if we don’t and they stay?

Good luck!

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