How I Changed Careers at 36 to Web Design

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Hi, I'm Chris and I'm super glad you're here. 7 years ago I taught my self-web design and freelancing. Now, I do my best to teach others what I've learned so they don't have to struggle as much as I did.

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I was pretty much a full-time musician for about 13 years.

To be fair, I was the worship leader of a church. Which is probably a lot different than what you’d think of in the usual sense of a “full-time musician.”

But, that’s the easiest way I know how to describe what I did.

Here’s the thing, I loved it.

I mean, you can’t really do something for that long without at least being mildly okay with it.

At least, I couldn’t.

But, like most passion-based careers there’s not a ton of money to be made. Which was fine for a long time.

But, eventually, I came to a place that I had to make more money. And, I didn’t want to leave my job.

You can read more about my story here.

Should I Change Careers at 36?

So, web design became a way for me to make extra money while my kiddos were sleeping AND I also got to stretch my creative abilities.

But, as time went on, I slowly realized how much I love web design.

Like love, love it.

Eventually, I came to the point where the demand for me to do web design and the demand for my full-time job came head to head.

And, I had to make a decision.

Do I keep going as a part-time freelance web designer while keeping my full-time job?


Do I flip the script? Part-time/volunteer musician and full-time web designer.

A Tough Choice

This was one of the toughest decisions I have ever had to make.

I mean I’d been doing my job at the same place for 13 years. I’d never imagined doing anything else.

I was comfortable where I was. I had a good handle on what I was doing.

My kids had literally never known me as anything other than a worship pastor.

I changed my mind at least 7 times over the course of a month leading up to the final decision. But, when the smoke cleared I knew what I needed to do.

It was time to make a big transition and change careers at 36 to full-time web design.

What I Learned

I imagine there are a lot of people reading this that feel as torn as I was. But maybe for different reasons.

Maybe you’re actually pretty tired of your job and feel stuck. You know you can’t stay where you are BUT you are so afraid of making the change you need.

Let me just say, you’re not alone.

I’ve talked to a lot of people who are considering career changes and a lot of the questions I get sound something like this:

  • What if I don’t like the new career?
  • Is this the right time?
  • Will I be able to get hired at all?

In my journey, I’ve found there are a few things you can do to help answer these questions before you even make the change.

So, here are a few things that I learned along the way that really helped me make the decision to change careers at 36 to web design.

1. Look at Your Career Like a Scientist

Most people will have about 12 different jobs over a 32 year span.

And, yet we put so much pressure on recently graduated high school seniors to pick an education path that will supposedly shape their lives for forever ??‍♂️

There’s a great book by Adam Grant called Think Again. He talks about the issue of Identity Foreclosure.

Identity Foreclosure is when someone chooses a path or personality, likes or dislikes, and refuses to change their minds no matter how much the evidence of them being happier or more content if they made a different choice would show otherwise.

Even when things get tough and everything points to the fact that this is a bad idea, you can’t quit because of the Escalation of Commitment.

That’s the idea that says, “We’ve come this far. We should probably see this thing through.”

I wonder how many people stay in jobs or careers they hate because of identity foreclosure or escalation of commitment.

What if there’s something else out there that’s actually better?

Well, the only way to find out is to look at your career like a scientist.

A scientist tries not to let emotions cloud their assessments or findings. And, this is tough for a lot of people especially if you’ve been in your job or career for a while.

You likely have friends at your workplace, people you’ve made deep connections with. You might even feel some sense of loyalty to your workplace.

I get that. Really, I do. That’s why I stayed where I was for 13 years.

But, those can’t be the only reasons to stay. It’s not that those things shouldn’t be considered.

Feeling a calling to the mission of your job AND having friends in the workplace. A poll from Gallup showed those were crucial components to loving your job.

But, that can’t be everything.

You have to look at your career on 3 levels

  1. The practical
  2. The personal
  3. The emotional

The practical is the nuts and bolts of your career. It’s the amount you can expect to paid over your life-time and how much time it will require of you every week to do a good job at your job.

So, do a little scientific research. Determine how much money you need to make and see what the salary ranges are for the career you’re in.

And, also look at how much time the job requires of you. If you want to have a lot of time for your family but your career requires you to work late nights and weekends, it might not be a good fit.

Consider all of those practical elements and if they all line up move on to the personal.

The personal is where things get, well personal.

You consider what makes you happy. What type of environments you really thrive in and what type of work really makes you come alive. And, also what skills you think you have or could potentially grow into.

I know for myself that I always need to be learning something new and pushing my own limits. It’s how I’m hard-wired. So, if I’m in a career or company that isn’t allowing me to explore growth and achievement, I’m going to struggle.

This might be a good chance to “phone a friend” and ask them for their opinion of where you really thrive. It’s sometimes tough to know ourselves super well and some trusted advisors can really help.

Finally, the emotional.

There are two parts to this.

The first is considering how much emotion you can handle.

Some jobs and careers come with A LOT of emotions. A stoke broker is going to deal with a TON of stress on a daily basis. A gardener won’t.

You’ve got to figure out how much emotion you like dealing with and then determine what type of career might fit.

The second part is determining how much emotion YOU’RE LOOKING FOR in your job.

Some jobs carry a lot of emotion. They’re cause based. The companies are on a mission to change the world with their products.

Other companies are more lifestyle based. They want to make a great product BUT at the end of the day, they’re happy with making enough money to provide for their employees.

In any career there’s a wide set of different companies that will be more or less mission/emotionally driven. But, some careers lend themselves to have more opportunities to be mission minded.

If all of those three factors line up in a specific career it’s likely that career will be a good fit for you.

BUT, if I’m honest, there’s no way to know for sure until you’ve tried it out.

Which leads me to my next point.

2. Try Before You Buy

These decisions don’t have to be an all or nothing situation.

But, for some reason I talk to a lot of people who ask things like:

“Do I keep going in a job I hate OR do I quit, sell everything I own and hope I find a job in a completely unrelated field in a few weeks?”


Drama much?

When I started I didn’t really have this option. I needed to keep making a steady income for my 3 kids.

So, I had to learn web design on my own in my free time and hope that the hours I spent not sleeping would pay off.

But, here’s the deal, you don’t have to jump ship right away.

Don’t know where to start? Try my Web Design Starter Kit Course.

See if you like it.

You’ll be able to tell pretty quickly whether or not this is something you could see yourself doing.

I often tell people that a good path to being a full-time web designer is by starting out as a part-time freelancer.

First, you get paid to learn and build a portfolio, BUT you also get to find out whether this is something you really want to do.

So, calm down and get rid of those false dichotomies. It’s not all or nothing.

It’s try-it-and-see-if-you-like-it. If you do, keep going. If you don’t, try something else.

3. It’s Doesn’t Have to Be Forever

For some reason, we have this mindset that whatever career we choose today will be the career we’re stuck with for the rest of our lives.

Finding a career you love is hardly ever a straight shot. And, guess what, as you get older what you want out of a career changes.

When I was making the decision to become a full-time web designer, I struggled with the idea that I would never be able to return to what I was doing as a worship pastor.

Thankfully, my boss helped me to have a better perspective.

As I was telling him I was quitting I was also sharing my fears with him.

That may seem weird to you, BUT you gotta remember this is someone I knew for 13 years. We’d been through more than a few things together and he’s someone I look up to and ask for insight even now.

His response was that you’ve got to look at life in seasons. Just because you’re leaving today doesn’t mean the door is shut forever.

That helped me see things clearly.

The key here is that you can’t burn bridges as you’re leaving. Don’t leave your old job with your middle finger up in the air while sabotaging the printer.

Think of this as something you can try for a bit. Give it a year. If it’s not something you want to continue doing begin considering other options.

4.You Don’t Need to Go Back to School

This will probably be my most controversial point. Trust me, people have argued with me about this already.

But the reality is, degrees don’t carry as much weight in web design as they used to.

I have a friend who learned web development from YouTube and now has a job at American Express.

Getting a job as a web designer has so much more to do with your portfolio than it does the degree you get.

I got a degree in business management.

I’m glad I got it. BUT, I haven’t had a job as an adult that actually required my degree OR any degree at all.

There are so many alternatives to traditional education these days.

Anything you want to learn is literally at your fingertips.

From online courses to part-time, online web design bootcamps there are so many opportunities to start learning and build up the skills you need to be confident in a career change to web design.

So, get out of the mindset that if you want to get a really good job as a web designer you need to pay someone $50k to learn.

That’s not true anymore.

5. Have a Few Backup Plans

When I first started applying for positions I had no clue if anyone would even want me.

After all, I was a self-taught web designer in his mid 30’s.

And, I had certain salary expectations that I couldn’t budge on because of my family.

So, going into the job search I had a few pathways lined out that were best and worst-case scenarios.

Best-case: I find the job of my dreams.

Worst-case: I ramp up web design freelancing and go full-time.

If nobody wanted me I was confident I could find enough work to make a decent income on my own.

Thankfully, the absolute best-case scenario happened. I work for a company I absolutely love.

But, if you’re in the same position I was, it doesn’t hurt to have a safety net.

That could be with a few months of living expenses in the bank. Or a rip chord exit plan if things start going south quickly.

Honestly, the safety plan was probably more for my own anxiety. Knowing that even the worst-case scenario was a realistic option helped me to take the leap and go for it.

6. Tell Everyone You are Looking

At the end of the day, resumes don’t get jobs RELATIONSHIPS do.

I love a book by Ken Coleman called the Proximity Principle.

In it, he outlines how important it is to get in proximity to the people you’re hoping to get a position from.

So, when I first started looking I told everyone. And, then I asked everyone to tell everyone.

You know what happened? I got connected with some great people that got me job interviews.

Your chances of getting an interview from being one of the 100’s or 1000’s of resumes submitted in an online job posting are pretty small.

You have to figure out a way to stand out. The best way to do that is through relationships.

Something else I did was find job positions and brainstorm who I knew that worked at those companies or had connections there.

This got my resume pushed to the front and opened up some opportunities I wouldn’t have had.

7. You’ve got to Approach it Humbly

If you’ve been in a specific career path for a long time the experience you have probably won’t carry over to your new career.

That’s super tough to accept BUT you’ve got to know that going into it.

There will be people who are younger than you that might be your boss…maybe much younger.

And, while you might have a lot more wisdom IN GENERAL than they do, they have a lot more experience in your new career field.

So, whether you like it or not they’re more qualified.

Switching careers especially past your 30’s truly is starting over. And, that’s okay.

Wouldn’t you rather be in a junior position doing something that makes you excited to go to work everyday rather than a VP in a career that is driving you to become an alcoholic?

Some things are worth more than money and position.

So, approach this new venture with humility AND be willing to put in the work with patience and dilligence.

Who knows you might advance quicker than you expected.

8. It’s Gonna Be Scary

When you’ve done everything you can to curb the amount of risk you’re taking before changing careers to web design the truth is it will still be scary.

But, what life change that’s worth it isn’t scary?

At the time of me writing this, I’m one month away from having baby number 4. He’ll be our first boy.

People ask me all the time if I’m excited. The answer is yes.

But, the answer is also that I’m freaked out.

Being afraid isn’t a sign that you’re making the wrong decision. It’s a sign that you’re normal.

So don’t let the fear stop you.

Keep going despite being afraid. Sometimes you just have to go for it.

When it’s all said and done, our careers don’t define who we are. They don’t define if we are happy or not.

I know plenty of people that are happy and content doing things I would have guessed everyone would be miserable doing.

But our careers can be a huge source of joy if everything else is lined up in our own hearts.

You might be wondering if a career change to web design is a good move for you.

Can I encourage you? Don’t sit on the fence. Get started on your journey and see where it takes you.

If you fail the world won’t open up and swallow you, right?

Someone once told me that the time will pass anyway. Why not try to go for something that could possibly make you happier.

I’d love to hear your story.

Did you transition from another career?

A sign pointing left and right


Hi, I'm Chris and I'm super glad you're here. 7 years ago I taught my self-web design and freelancing. Now, I do my best to teach others what I've learned so they don't have to struggle as much as I did.

Every week, I write an article and release a podcast episode. Sign up if you want to get notified when that happens.



  1. That is very brave of you Chris, you really jumped on the vast ocean and came out victoriously. I am also thinking of doing the same thing, from working 8-5 job to doing a job i love and having my passion as an adventure tour guide. Really wanna do this soon thanks for sharing such great inspiration.

    • Chris Misterek says:

      That’s awesome, Alex! You can do it, man. It feels scary especially with everything that has happened lately BUT it’s more than doable.

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