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I am a self taught person, 40 years old. My highest education is middle school, or whatever the 10th year of education is called in your respective school systems (not the best education indeed).

For the past 10 years I worked as either a Chief Technologist and Chief Technology Officer, in two different companies. The first company as CTO, in a company I founded. The second as CT, in the company that acquired us.

I always thought, and still think I am fit for this type of position. I think I'm great at choosing the right people, I know what strategies work and how to motivate etc.. The list of what I'm good at might be irrelevant so I won't make a long list. But, I have some serious short comings too.

The biggest:

I never learned to code, so I'm not a programmer in any sense. After a little more than 10 years, I have exited the company that bought us for various reasons. Mostly disagreement in management styles.

I have a significant amount of shares in this company, but they are not public. Selling the shares right now is simply not possible. I therefore require an income. I could start a new company, but have recently become interested in simply "getting a job" for the first time in 25 years.

To get a position as CTO, despite my track record - is going to be challenging. I need to be able to show I know my things on the nitty gritty details, even if I won't be hands on.

The question then becomes; how do I know if I will succeed, if it's going to take me a year or more to become good enough? I'm worried that even trying my hardest I might not be able to become as good as I need to be.

Any advice on how to assess this? How important is personal suitability and talent over pure dedication and willpower?

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  • How did the acquisition of the company you founded result in no money received? Didn't you have options to be paid in cash instead of 100% in shares? And shares that can't be sold is worth exactly 0. If your acquisition company goes bankrupt, you just got ripped off.
    – Nelson
    Jan 24 at 8:17
  • 2
    How do you know if you can become a skilled anything? You invest many hours in study and practice, and you find out if you hate it, like it, don't care about it, have an aptitude for it, have no aptitude fore it, have the interest and patience to carry you past the things that don't come immediately, trust that you can learn. You may find you prefer to do it as a hobby rather than at a professional level. But the only way to find out is to decide you care enough to make a serious investment in trying.
    – keshlam
    Jan 25 at 16:24
  • Old joke: "Do you know how old I'll be by the time I learn to play the piano?!?" - "The same age as if you didn't." Jan 25 at 23:59

4 Answers 4

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I could start a new company, but have recently become interested in simply "getting a job" for the first time in 25 years. To get a position as CTO, despite my track record - is going to be challenging. I need to be able to show i know my shit on the nitty gritty details

If you are considering "simply getting a job", be open to the possibility that such job may be something different than a CTO.

The question then becomes; how do I know if I will succeed, if it's going to take me a year or more to become good enough? I'm worried that even trying my hardest I might not be able to become as good as I need to be.

The cold, but true, answer is you don't. No one knows for sure if they will succeed, or if they will take X time to be "good enough" (quite relative that word).

Be careful with doubt, it can be dangerous. Don't preemptively worry about "I won't become good enough"; work steadily towards that goal and you will then know if you could or could not. Many goals that may seem unattainable can be achieved by focusing on small steps that bring you there.

And finally...

I've for the past 10 years worked as either a Chief Technologist and Chief Technology Officer, in two different companies. The first company as CTO, in a company I founded. The second as CT, in the company that acquired us.

Not only are you self-taught (which is something great and admirable!), but you also founded a company which was then aquired. The first thing tells me you are capable of many things (like founding a company!) and the second one tells me such company was doing good at least, to be acquired by another.

You also have 10+ years experience in the roles of CT and CTO, so your experience backs you up in case you were to "simply getting a job" elsewhere as CTO/CT.

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  • When looking at the jobb titles around me I see several that are senior and where your skills would be interesting: you could look for large companies needing agile product owners, you could look at consulting companies needing team managers etc. Of course it would make sense to apply to CTO positions as well but they are probably not as numerous.
    – lijat
    Jan 24 at 4:32
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How important is personal suitability and talent over pure dedication and willpower?

Well one assumes suitability and talent does matter, and that you can't simply be a talentless Walter Mitty.

If you've been a CTO in any real sense, then presumably you have some relevant technical background, or are competent in grasping and communicating about technology matters (even if you'd defer to your staff on fine details)?

If your position has always mainly been that of a people manager, then I would suggest that you consider senior management positions in general - and not limit yourself to positions where employers might well expect a relatively hands-on technical manager.

In your circumstances, it may be easiest to find another position through your social or professional network amongst those who trust you or know your reputation, because when seeking employment on the market, employers will often be wary of hiring those who are more accustomed to being employers themselves rather than being employees.

Not only does being an employer imply that you're accustomed to being in charge with total oversight and may lack the skills to coordinate with those who are in charge of you, but it also often implies that you're capable of earning a lot more money, or that your personality is more suited to the activities of entrepreneurship (which is pretty much what you acknowledge has been the case in your life hitherto).

Only senior employed managers in large corporations are capable of out-earning a relatively small businessman, but it requires a completely different kind of competence, so you might find it relatively difficult to find a pure "job" except where you're either a full partner with a stake in a small business, or at least a trusted lieutenant for the owner(s) of a smaller business (perhaps those who are looking to semi-retire, or are becoming spread too thinly across multiple of their businesses), which returns to the point about using your network to find such a position.

As an alternative, if the acquiring business in which you ended up as CT was a decent-sized business, and if you really did perform well in the role for several years (rather than simply being grandfathered in by your ownership of the acquired business, before gradually sliding out unhappily over differences in "management style"), then it might pay to de-emphasise your status as an owner and small company founder, and emphasise your achievements as an employed executive and people manager, in a larger company you didn't found and weren't the controlling owner of.

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I tried making the transition from being a key member of a startup company, to simply "getting a job" as you describe it, and the end-result wasn't good; I absolutely hated it, and got very frustrated with the decisions the directors were making.

You mention that you left the last company over a 'disagreement in management styles', so I think you are in danger of going down the same path. A not-hugely-challenging senior post may appear appealing in the short term, but very soon your entrepreneurial spirit will take over, and frustration with the management decisions could start building.

If you don't want to start up another company, then look for small startups that need a hand expanding & managing their IT systems; they'd probably welcome you with open arms, and you'd get you'd get the chance to build & run the department your way.

With regard to your concern about not being good enough, the saying 'in the valley of the blind, the one-eyed man is king' springs to mind. If you choose to join a team of highly-experienced people, you may well feel inadequate in comparison. However, if you are in a small team trying to bring something new to the market, you'll all be learning on the job, and your experience (as shown by your track-record) could be highly valued.

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  • Right, it is helpful to aspire to be the best of 3 people interviewed for a position. Always worked for me. Jan 26 at 0:02
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Your best chance for employment would be to apply for jobs that are not coding/programming positions such as manager, scrum master, project manager, director, VP of engineering, etc...

You don't need to know how to write code to be successful in the IT world because you can work in the non-coding roles that manage people and projects. You already did that successfully as the CTO of your previous company. So, keep focusing on those kinds of "manager" roles.

Many companies may not be interested in hiring you as a programmer because you have no real coding experiences with a real company.

Fortunately, you already have great experiences in managing people and projects. So, you should apply for those "manager" positions.


I have known a few people who have zero coding experience, and over 30 years, they gradually become managers, senior managers, or even VP of engineering for very big tech companies.

And, these people switch their jobs from one industry to totally different industries. Although these industries are not related, the companies are willing to hire them because these people have good talent in managing people/projects.

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