How To Get Into Tech By Overcoming the Catch 22 Effect

May 09, 2017

How To Get Into Tech By Overcoming the Catch 22 Effect

I’m borrowing one of Joseph Heller’s ideas from his infamous book Catch-22 to describe how you must be feeling trying to get your first programming job in the tech industry.

Freelance Catch 22

Catch-22 refers to “a paradoxical situation from which an individual cannot escape because of contradictory rules.” (source: Wikipedia) For example, no one will give you a job without experience but you can’t get experience without a job.

To set the stage of the things I learned that can help you overcome the Catch-22 Effect, I’m going to tell you the story of how I got started.

The Story of How I Got Started and Inadvertently Landed a Job

When I first moved to California from the Midwest, I had no professional experience in web development. So how did I land my first programming job?

In a sense it was pure accident, though looking back I can distill some ideas on how it really happened in retrospect.

I was trying to get a SaaS (software as a service) application going, and though it got built, it never really took off. Alas, it turns out trying to start a business was a bit harder than I thought.

Freelancing Time

So to see if I could keep the entrepreneurial thing going a little longer, I decided to try my hand at freelancing. My current self is laughing at my old self at how little I knew about best coding practices then.

But I was determined and I did work hard. I got started by helping someone out on their website for free. I got a testimonial out of that, which helped in my marketing.

Minimum Viable Portfolio Site

Next, I turned my blog into a minimum viable portfolio site (I have since created a separate portfolio site which you can see at

Here, I made sure to display….guess what? Yup, testimonials. This was so that any potential prospect who came to the site would see that I did great work endorsed by others.

Chasing Leads on the West Coast

Eventually, I found a steady client through (before it became Upwork). I was successful enough at it that the team who hired me offered to bring me on as a business partner to help with the technology stuff. Alas, I decided not to pursue it for various reasons.

Once you find that first client, then I noticed you begin to feel more confident and more clients keep showing up. Plus, you get to keep building up your portfolio. That’s what happened to me at least.

I did learn I was undercharging

One of my clients did tell me that they loved the work I did because I delivered on time at half the going rate of others in the area. Oops, I was undercharging and didn’t realize it.

Eventually, I decided I might be better off getting a job. So I started looking around.

Recruiters and Rejection

When I first started job hunting, I remember getting rejected more times than I would have liked to jobs that I thought I was a shoo-in for. This is in stark contrast to today when I find it much easier to get multiple offers, partially due to the demand and partially due to my experience.

What hiring managers want

In my experience, hiring managers in their mind have the following checklist, in the following order:

1 – Ability to get things done

2 – Seems to be a fast learner

3 – Has experience in the actual technical stack they use at their company

4 – Worked in a production environment before

Senior level programming candidates usually are able to demonstrate this.

Always willing to face rejection

Needless to say, when you’re first starting out, you might be lacking in certain areas, especially experience. This means you’re going to get rejected a lot more.

It can feel disheartening to get rejected from a job that you really wanted. I’ve found it helps to think of it less as hunting for a job and more like you’re running a sales funnel.

Let’s examine the following statistic from this article at HubSpot.

An average buyer gets 100+ emails a day, opens just 23%, and clicks on just 2% of them.

Let’s think of that average buyer as a technical hiring manager. He or she is under all kinds of pressure to deliver the product and wants the most experienced and qualified candidate available.

The hiring manager probably has to sift through a pile of resumes and pick out the most promising ones to interview. This is akin to getting bombarded with 100+ emails a day and opening 23% of them. Eventually, they will interview and choose to hire 1 or 2 people from that pool.

Is it any wonder why you should expect to face a lot of rejection when you’re first starting out?

A Happy Ending

Eventually though, I did land a position at a local college. Now colleges and universities don’t have the best pay, but they do generally have good work life balance and actually can provide you with a good experience as a lot of smart people work there.

Certainly, that was my experience. Eventually the college department I worked in began laying people off due to a lack of federal funds. Thus, I decided I it might be good to explore the startup scene so I departed for private industry. But of course getting that first job opened the door to getting multiple offers and overcoming the Catch 22 Effect.

The Framework for Overcoming the Catch 22 Effect

So how can you overcome the Catch 22 Effect? Here are the steps I’ve distilled from my journey.

Step 1 – Portfolio Pieces

I’ve always frowned upon free work. People try to make it seem as if they’re like they’re doing you a favor by providing you with experience.

But I’d argue even something as simple as a well-crafted brochure website is a tremendous value add and not something that should be done for free. But if you have to do it, you have to do it.

At the very least, make sure you get a testimonial out of the free work. That could be the most valuable move you make as it is third party proof that you can deliver valuable results.

The most important thing is to build up your portfolio. It helps you in your job search in the following ways:

  • Talk engagingly about past projects at interviews
  • If it’s online, it allows prospective clients (or employers) find you easily and browse through what you’ve done

Step 2 – Testimonials

Needless to say, I believe having testimonials helped me land freelance clients and make sales. Every professional marketer will tell you how critical they are.

Make sure to get them!

Step 3 – Minimum Viable Portfolio Site

If you’re a front-end coder, I’d really strive to have the best looking portfolio site you can. Try to see if it can pass the Google page speed test, as I’ve heard some employers will run your site through that tool before even deciding to talk to you.

If you’re a back-end coder, your site doesn’t have to look as nice, provided you have the skills that are in demand as a back-end coder.

Step 4 – Determine Where You Are In the Value Chain

This is one of the hardest things to do. Humans are pretty subjective judges, but you should still try to see where you are in terms of skill in realistic terms.

If you’re starting out, you’re probably not ready to be a technology lead at say, Google. But you’re also probably not as inexperienced as you think you are.

Even if you’ve only been at it a few months, you know more than someone who hasn’t been at it for a few months. For example, you probably know more than that small business owner who wants a brochure website.

Having a realistic idea of where you are in the value chain can help you decide which jobs you are most likely to land and thus, which leads to pursue.

Step 5 – Creative lead generation

I’ve listed 3 potential lead generation opportunities below in order of lowest to highest profitability:

  • Upwork (formerly Elance and oDesk) – You tend to find people on here who are looking for “cheap bodies” to throw at their idea. But I’ve also found some real gems on here as well, including one local client.
  • Your network – I have to admit, I didn’t use this as well as I could have. But getting a warm lead that already knows what you’re capable of is a really great way to have a happy customer and repeat business.
  • Presentations – One business owner I know effectively uses presentations to land high-value clients. Presentations work because you come across as an “expert” and make people more receptive to your message.

Step 6 – Carefully crafted communication and soft skills

Now when you’re first starting out and you don’t have as many of the hard technical skills employers are looking for, it can really behoove you to have soft skills.

Be a pro at communication. Follow up immediately and always be polite and professional in your messaging.

Be sure to emphasize what makes you the best person for the job. And of course, it goes without saying, please don’t lie about your skills. You will be found out when you’re asked to put them to use.

Step 7 – After Action Review

The Army has something called an After Action Review to basically figure out what went wrong, what went right, and what they could do better next time. I’ve applied this strategy to all my job interviews, especially the ones where I get rejected.

I even have a script I use to ask for honest feedback.


Once you have Steps 1-4 down, it comes down to a well-honed marketing message and a willingness to go out there and sell yourself repeatedly. You can use an after action review to assess what needs to improve along the way.