You may know my name, but I’m a fraud

I’m a total fraud.

On the surface, it appears that I have everything together. I’m the founder of a fairly well-known (in the tech community) startup. If I were to assume, most people probably think that my company is doing well. I’ve been featured, covered and spoken about in many tech publications, in fact, just this week. I’m called upon for my “expert” opinion by these same publications from time to time. I’ve invested in two companies, not including my own and I’m contacted on a regular basis for pitches/advice. Oh, and I’m an “advisor” to a handful of companies.

What nobody knows is that I’m dead broke and looking for a job. My funding stream has all but dried up and I’m out of options. What’s worse, I’ve lost all confidence in my ability to execute on even the most fundamental business tasks, let alone anything that I once considered myself good at.

And I’m giving advice to others? Are you kidding me?

The problem is, my company isn’t failing, I’m failing and I don’t know what to do about it. How can I help others if I can’t even help myself?

Don’t get me wrong, while the company isn’t failing, it isn’t doing great either. It’s just doing, which is an extension of me.

Last week I started looking for work and I’m embarrassed as hell. I’m too ashamed to reach out to my contacts because I don’t want them aware of the situation that I’m in. On the other hand, if I’m to get a job anywhere, my contacts are my best shot.

Honestly though, I can’t help but wonder who would want to hire me. It’s clear as day that I’ve been an entrepreneur all of my career. With just the tiniest bit of research they can see that I’m still actively working on my own company. And, I’m certain that anyone I speak with at this point can clearly see my lack of conviction in anything that I say. Frankly, I wouldn’t hire me.

While I’m being honest, I might as well state that I really don’t want a job. Additionally, I’m not sure it’s fair to whoever is willing to hire me. I have no intention of sticking around. I’m only looking for a job out of necessity and will only be around as long as it takes to get my own shit in order.

I feel like a terrible person for even writing that, but it’s the God’s honest truth.

Job aside, I think I’m just sad and afraid.

I’m sad that at this stage of my life and career, this is where I’m at.

I’m afraid that I’ve missed my window of success, whatever that means.

I’m afraid (and sad) of being an employee.

I’m afraid that I’m getting too old to still be in limbo.

I’m afraid that what I think about myself might actually be true.

I’m afraid that those that look for my opinion and advice will see that I’m a fraud.

Bottom line, I’m afraid of being a failure.

Sometimes the hardest advice you have to give, is the advice you give to yourself. But, I can’t seem to even do that lately. I’m completely lost and looking for answers.


  • How old are you? Its a cliche by now but many people found success past their 50’s. Sure maybe not in tech but thats because the press has a fawning for young-uns.

    You say your company is doing fine, but its not able to pay you a decent salary?

    What about just doing consulting? I’ve been bootstrapping my startup for over 4 years and use consulting as a means to pay the bills (yes my startup sucks and I should shut it down since I don’t make jack).

  • Good on you for honestly expressing yourself here. A first step.

    In reading your words, I hear you orienting a lot to what others will think of you and internalizing it. If you filtered out that noise–“You shouldn’t be here at this point in your life, you’ve missed your chance, you’re too old, you’re a failure”–I wonder what would you’d hear instead?

    You’re seeking. Often, our questions are more important than our answers. Questions point us in a direction. They also clue us in to what needs to be heard. What is asking to be heard by you?

    Your last line said you were looking for answers. What are YOUR questions?

    I sense you feel alone. You’re actually in the company of many others. People often feel the things you wrote at some point in life, but, don’t often say it. You did say it. We all hide from ourselves. It’s being human. Don’t box yourself in by imagining you’re the only one who has felt like this.

    Take another step. Talk honestly with someone you trust. Ask them to really listen past the things you internalize. The things you catastrophize. The things you idealize.

    Read your post out loud to yourself. Listen in to what you really need. What you need to change.

    All the best.

  • Your post hit me. I was where you seem to be now 2 years ago. I started privately consulting off the grid in house with a “normal” company and really got my bearings. I’ve never had a real job, and working in some one else’s office has grounded me and taught me a lot. I also recommend you find a therapist and start talking – not someone who says the specialize in coaching entrepreneurs.

  • Don’t worry. It’s just the start of a crisis. It might end sooner than you think now that you acknowledge all that. Focus on doing something bigger, that would benefit the world. All those positive thoughts from people using your stuff will get back in your direction and you will feel better even if you don’t make too much money.

    Cheers

  • true story, I started driving for lyft to generate some cash on my weekends and honestly I felt a lot better. this is not an ad, it’s just some advice. you don’t have to tell anyone, it helps your self esteem, gets you out of the house and gets you interacting with other people. and you don’t have to tell your friends you need the money. but over time I have started telling them because if the founders of airbnb were eating fucking cereal when they made, it, then this is no different.

  • You know what. That’s how it is for a lot of people. Me included. I’m 40 years old.

    Some days are good, and some days you wake up with a knot in your stomach and it’s there till 3 at night.

    But you’ve been around for a long time right? You know how it works. Patience and experience make all the difference. Hang it there – ride it out. Eventually the fog clears away, and a single moment can change everything.

    Love.

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