The Late Career Bloomer’s Guide To Catching Up

The Late Career Bloomer’s Guide To Catching Up

Whether you’re about to attempt a career switch or starting late from a blank slate, catching up to the rest of your new field can be intimidating. Here’s what you can do to be on equal footing with your peers — or even get ahead of them — as a late career bloomer.

Pictures: UFV Career Fair 2014, Startup Stock Photos, Official US Navy Page, Samuel Mann, COD Newsroom, CollegeDegrees360.

Find Freelancing Opportunities

The Late Career Bloomer’s Guide To Catching Up

Regardless of your industry, the full-time job market can be competitive. Rather than looking for a full time job, keep your eyes open for opportunities for freelance work. This will get your foot in the door with companies who may be interested in hiring you full time if they have room in their budgets, and if they find your work particularly valuable.

Freelancing will also force you to practice your hard skills. For example, my friend had started a promotions company and heard I knew how to use Photoshop. He asked me to design some promotional posters for him. I had never made an event poster before, but using others as references, I designed something original in Photoshop. He loved it, paid me, and asked for more. As I created more, posters became much easier, and I got much more familiar with Photoshop. I also became a lot more confident in my now-validated skills.

Freelancing also exposes you to many different situations, which can be interesting material to either share on your resume or to express in an interview. Better yet, you don’t have to leave your day job or school to start freelancing.

Lastly, freelancing forces you to learn about negotiating and pricing. These techniques (like the briefcase technique) and this skillset will put you at an advantage to the rest of your peers.

Volunteer Outside of School

The Late Career Bloomer’s Guide To Catching Up

You may be in school taking courses for the first time, or this may be your second time through. Although school clubs are the conventional way to pad your resume with extracurricular activities, it also makes sense to volunteer your time to an organisation outside of school (try looking on LinkedIn). You’ll be able to connect with a greater range of people.

Some organisations or movements, like Pencils for Promise, are technically school clubs, but have a strong presence off campus. You’ll be working at a larger scale and tackling different types of problems that you may not see inside a smaller standard school club.

Additionally, you could also volunteer for an informal internship. You could reach out to local companies and ask them if you can stop by one day a week and do administrative work for them (or whatever work they need taken care of). The feasibility depends on certain industries, though. For example, although it could be straightforward to volunteer and answer phones at a doctor’s office, it might be more difficult to do for lawyers.

Nonetheless, this helps build experience and your network throughout the year without taking up too much time in your daily schedule (if you’re in school, this will depend on your class schedule).

Also, while it’s good to be valuable for a short time, if you get too good at being an assistant, then people won’t be able to see you as anything else. Use it as a way to get your foot in the door, and slowly start branching out and learning where else you can contribute.

Create (or Collaborate on) Side Projects

The Late Career Bloomer’s Guide To Catching Up

Even though side projects may seem like a hobby, they can be a significant advantage when connecting with new contacts or recruiters. Most people don’t try side projects because they seem like a peripheral concern, and actually take some creativity and problem solving to properly execute on.

The premise of a side project is pretty straightforward: identify a problem, build something to solve it, and show your solution to people who can use it. A lot of realistic side project ideas come from information gaps between newcomers and experts (e.g. creating ebooks, blogs or setting up a small trade event for your local experts in your industry). You can interview experts to get the information you need to inform newcomers (you’ll ask great, relevant, questions because you’re a newcomer yourself). Even if you’re busy with a day job or school, you can still create a side project outside those hours.

Similar to freelancing, side projects can force you to develop new hard skills. For example, a few years ago, I created an ebook to explore internet marketing. I’d noticed that students were having a hard time getting jobs because they didn’t have any credibility (a chicken and egg problem), so my ebook was about how they could use guest posts to build credibility. Prior to writing it, I was already a frequent writer for a national independent media outlet and had guest posted in several blogs.

The ebook connected me with a ton of students and — surprisingly — entrepreneurs. I designed the book myself in InDesign (based on skills acquired from freelancing, actually). My friend helped me design the website and code it in HTML. I learned how to use MailChimp to generate leads. I picked up more hard skills in that three-week push than I had in a full year at school.

Meet One Person in Your Industry Per Week

The Late Career Bloomer’s Guide To Catching Up

You probably don’t know anyone that can give you a job that you’d like (since you’re reading this post), so you’re going to have to figure out who these people are. You’ll then meet them and make a great impression. That’s much easier said than done, so let’s unpack this a bit further.

Firstly, don’t go to information sessions or networking events. For the most part, they’re ineffective. They may seem compelling because all your friends and peers are going, but that’s exactly the problem. Usually, there are tons of students or early stage career people at these events trying to meet a small amount of important people.

Instead of mindlessly going to networking events, try to email and meet just one new person in your industry every week. If you’re a student, most people will be excited to meet up with you (or at least curious) since you’re still in the academic world and, thus, non-threatening. When you first get in touch with them, don’t lead with your need — instead, learn from their knowledge or expertise, or figure out how you can contribute to what they’re doing.

If you’re not comfortable with cold emailing people, cold call an office or show up in person. I realise this sounds unconventional, but I actually did this myself when looking for a job in advertising. After asking the secretary to speak with someone in charge of recruiting, I was able to connect with them on a Skype call and on LinkedIn.

While I ended up with another opportunity that summer, it was a pretty insightful call and I had a chance to subtly make my case for an internship. Be forewarned, though: this plan could backfire if you are particularly aggressive or assertive. Be grateful for even just a minute of someone’s time, because they could be doing something else that day. You may also have to do it more than a couple of times in order to really get a good grip on it.

Read Like Your Livelihood Depends On It (Because It Does)

The Late Career Bloomer’s Guide To Catching Up

Even though it’s intangible, information is extremely valuable. It’s also overlooked far too often. The best of your peers have probably acquired a lot of information while you didn’t. That’s alright, because books and other people’s experiences can help you catch up. You’ll learn from other people’s mistakes, and the history of your trade.

Make it a focus to regularly read interesting biographies and articles of people in the field you want to explore. Even if you’re working as a part-time staff member in retail for now and plan to stay in it, learn how the best retailers or brands started — who the entrepreneurs were, what their journeys looked like, and which lessons apply to you. If you’re working a job in fast food and don’t plan to stay in it, figure out where you’re trying to move towards and read up on that industry.

Depending on your industry, news can be important as well, so keep up without spending too much time on it. Books and longer articles often have more timeless knowledge, which is can be more valuable than only keeping up with the rat race of news.

Catching Up Means Working Harder and Smarter

Starting a new career or making a switch is no walk in the park, but it’s definitely possible to quickly get on par with your new peers. Look for freelance work and non-school volunteering opportunities. Work on side projects and meet new people. Read both the news and books, because information is crucial.


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