Unconventional Ways to Try Out a Career Before You Commit to It

This post may contain affiliate links. See our affiliate disclaimer here.

It’s hard to count how many friends I’ve heard tell me this exact same story. “I went to college for four years to become an accountant. I graduated and found a job with a big accounting firm (enter applause for accomplishing the dream job, oh wait). Then I realized I hated accounting.”


How is it possible so many people are spending three, four, six (for you super, super seniors) years on a degree without ever having tried it out even a little bit? It seems counterintuitive to marry a career without ever taking it out on a first date.

After graduating from college it took all of nine months for me to figure out that I had no passion for software sales. I went to school thinking I was going to be an entrepreneur, but when I graduated with no thriving business or investment offers, I joined the rest of my peers in the search to find a job. The problem was, I felt I had a lack of options. I didn’t feel I had a lack of talents, I just wasn’t well educated on the vast amount of jobs out there.

In college we were lectured on the job titles 101: marketing, management, accounting, etc. But outside of the basic titles, I knew very little. I now realize most schools are doing a poor job on educating us on just how many options are truly out there. How can I prove this? Ask a group of college graduates what they want to do moving forward and you’ll receive a grandiose of blanket statement job titles that nobody ever actually uses, such as, “I want to do branding.”

As of this moment I haven’t met a single college graduate who was immediately hired to a Fortune 500 company to be in charge of “branding.”

So, what kind of real options do we have when it comes to figuring out our career?

This past year during Hourly America, I spent days on a farm, as a Zombie at Six Flags, as an electrician, maintenance worker for the LA Angels Minor League team, stand up paddle board guide, scooter technician and a whole bunch of other pretty epic jobs I never knew existed. While my project was a crazy personal goal of working a job in every state, it educated me on the huge number and diversity of jobs readily available to those who’re looking.

After working my fiftieth job this past week, I’ve been thinking about how other people can try out a similar strategy of “trying out different jobs”. What if there was an option where we could try out different careers before committing to them? A way where we don’t spend tons of time wasted doing something we don’t love or isn’t helping us move forward.

Here is the concept I came up with, try speed dating with different career options.

The definition of speed dating with careers? 

A way of trying out different career and job options in a short window of time. While the amount of time can vary in length, the purpose is to speed up the process of figuring out what we want to do with our lives by putting ourselves in real jobs, gaining real experience.

This method of speed dating with jobs is an alternative to graduating from college, taking the first job, and sticking with it for 4-5 years because we “need the experience.” If we fall into the trap of sticking with the first job we land right out of college, we’re likely to stick around for the wrong reasons (i.e pressure from family, friends, coworkers telling us that we have it good, why leave?). I’m definitely not recommending we leave the first job after college, just for the sake of leaving. If the job is awesome, then by all means stay. But most of the people I know wouldn’t recommend marrying the first girl we ever took on a date either, just saying.

At times I felt a dilemma before leaving my sales job. I wanted to be loyal to the company that gave me a chance. I wanted to stick with the business, help them grow, and show my appreciation to the CEO who brought me on board. When I voiced my distaste for sales, I was met with immediate pushback. “Heath, you’re so good at sales. Why would you give that up to pursue writing and making a documentary?”

My first inclination was to feel anger and resentment. But he had a point, my sales record proved I could do a good job in my current role. Up until that point, I had zero proof that I could make it as an author or film maker. But the problem was, this was my VERY first job outside of college. Who is to say that my talent for sales could even compare to my writing or film making capabilities? I had never even tried. While I could utterly fail at both, there was one thing I knew: I didn’t like sales and wanted to try something new. I wasn’t sure what that new thing was, but I knew it didn’t come in the form of RFP’s or Salesforce.com.

The enemy here wasn’t my boss, he was looking out for my best interest. The enemy was me, telling myself the lie that I might only have the skill set for one thing. Here’s what I learned from this experience.

Our twenties aren’t about finding the first job offered to us and spending the next forty years of our life working our little heart away. Companies are coming and going faster than ever and it’s up to us to figure out our place in this modern workplace. There are thousands of jobs out there waiting to be claimed, and I find it extremely hard to believe we should know precisely what we want to do with our lives after walking across the stage for graduation. I find it even more difficult to believe that the first opportunity we’re handed is going to be the one that we take all the way across the finish line.

So, what does it actually look like to speed date with different career options?

If you have some financial runway and you have a month or two off, such as summer time, that’s a perfect opportunity to give this a try. Instead of trying to find one place to work, see if a company will let you come in and work for a two week trial period. Tell them you’ll work hard, and then wait and see if you enjoy the job. This will also let them evaluate you and see if you’re a good fit for their business. It has a positive benefit on both sides.

If they say no, ask if you can do the work for free. The experience in itself is worth not getting paid for that two weeks. Most people wouldn’t see it like that, but ask yourself this, how much would it be worth for you to not spend a year of your life working a job you dislike? What would that year of your life be worth in monetary value? If that’s worth two weeks of not being paid, then give it a go.

If you’re like me, making decisions can sometimes be the worst thing in the whole world. If this is the case, pick your top five career/job options and test them out. You might find out that none of those positions may be of interest to you, but at least you’ll be five steps closer than most people. The alternative is going to work there for two or three years before you realize it’s not for your. Sure, sometimes it takes longer than a week or so to get to know a job fully. In fact, I know for a fact it takes longer than a few days to fully comprehend and feel comfortable in a job, this timeline is typically months or years. But more often than not you can get a hint of whether you’re going to like the atmosphere, culture, people, or some of the job description in a much shorter period of time. A lot of these factors won’t take you years to learn.

Something else to keep in mind when it comes to trying out a job for a short stint, realize that you won’t be any good at what you’re doing. If you can feel comfortable not being great at something yet, speed dating with jobs definitely will benefit you.

I know it might sound like a crazy concept. How on earth am I going to get multiple companies to hire me when I can’t even get one to hire me? I promise you, it’s possible. Be upfront with them when you’re putting in an application. Tell them you’re trying to find a career that best suites you and be totally candid with them about why and how you plan on doing it. If you still can’t get a “career trial,” move onto the next option.


If you can’t get your foot in the door to actually go and attempt a job, try apprenticing somebody who’s been doing it awhile. Some positions it might be impossible to walk in and try it out, because you have to achieve a certain status such as a physician or electrician. Instead of having to actually go through all that training, see if they would allow you to just apprentice them for a few days or a week.

During Hourly America I apprenticed an electrician, which is a highly technical job. You have to have a lot of certifications and hours under your belt. Working alongside him for the day gave me an opportunity to see first hand what a day in an electrician’s shoes is like, without me having to go to a trade school for two years. I was able to ask him questions about the variety of projects he’s able to work on, what his normal day is like, etc.

Practical advice on how to execute on this: Call or email 20 electricians (or whatever position you’d like to apprentice) and ask them if they’d be willing to let you come and shadow them for a short period of time. Also, make sure to tell them why. As in, I think I’d really enjoy being an electrician, but would really like to know more about the job itself.

There are so many people out there who would be more than willing to help out and share their passion.

Lastly, if apprenticeship or job dating is out of the question, it’s time to conduct information interviews.

Go out and interview a ton of people, as many as you can, about the kind of job you want to have. How do they enjoy it? What are the pros and cons of working there? Why have you stuck around? Would you recommend this role to someone with my skill set?

Try to interview five or ten people before you go to work at a company or even apply. You don’t have to take their advice as point blank truth, because everyone is different and their interests are likely different from yours. But sometimes this interviewing process might be able to give you a pulse of what kind of job you’re about to walk into. If you talk to someone and they say, “I enjoy what I’m doing, but the time commitment is high. I don’t get to see my family as much as I’d like.” If spending time with your future family is something that’s important to you, that job might not be a good fit. Gathering this initial data is another way to dip your toe into something before you fully commit to devoting a lot of time in any particular career.

The important thing I try to reiterate to myself is I don’t have to have it all figured out while I’m young. Our twenties are more about figuring out what we don’t love, so we can cross things off and be one step closer to finding what we do love. Our career, like our lives, is a giant practice field and is worth experimenting on. If you find yourself in a similar boat, working a job that doesn’t have you fired up, then I’d encourage you to give one of these tactics a try.

In looking for a quote to end this post, I couldn’t find anyone better to quote than Steve Jobs in talking about searching for our passion.

“If you haven’t found it yet, keep looking. Don’t settle. As with all matters of the heart, you’ll know when you find it. And, like any great relationship, it just gets better and better as the years roll on.”

2 Responses

  • This is so useful and brilliant. It could probably work the other direction too, don’t you think? Start with “interviews” and when you have a better sense of your direction, volunteer to work for free or work temporarily.

    • Totally! I think it could definitely be a mix and match type thing 🙂

Comments are closed.