So You Want to Reinvent Yourself? 8 Steps to a New Career Path

If you’ve been following along, you know that I held a Q&A session on career topics for an online community.

ChrysalisMany of the people who had questions were aspiring entrepreneurs in STEM professions – which is highly representative of my client base here in San Diego. We’ve become quite the hub for tech start-ups and lots of exciting things are happening locally. As you might imagine, I love talking to people about this stuff. Having seen so many of my peers succeed on their own terms, I’m enthusiastically spreading the word that this is a viable option for people!

This next Q&A comes from a young man (okay, he’s my age, but I’m still calling him young!) in the Northeast who’s been struggling to put all the pieces together and reinvent himself to forge a satisfying career. He has lots of marketable skills, but needs a little help with packaging it all in a way that feels right to him.

His Question: After attending Burning Man  for the first time, I had the courage to leave what I decided was a badly matched IT career. That was about 5 years ago. Since then, I’ve traveled and done temporary, contract, and freelance work, but I have yet to find a consistent way to earn money that leaves me happy and not insane.

I’ve ventured back into the IT world a few times since the money is so attractive, but I find myself going crazy within 3 months. I love the work itself and I’m good at it, but the daily grind wears me down. I can write a decent resume and I interview really well. In fact, I’ve been offered 3-4 jobs in the last 2 years that I turned down because, well, I don’t know why – I freak out and say “no.”

I fall firmly into the category of WTF DO I DO!?!? I’ve spent years obsessively reading blog posts, taking personality quizzes, surfing craigslist… And still have no idea which direction I should go or how to get started. I have a huge breadth of knowledge and a lot of great (albeit not ordinary) experience. I am a successful leader in my community and can “heard cats” like a pro. I think all of that has served to confuse me more when it comes down to it.

My Answer:  Reevaluating your career path after a transformational experience is really normal; it can be the kick in the pants we need to realize that things aren’t working and it’s time for change. You’ve realized that a traditional IT career isn’t for you, and that’s a great start! But now what? Whether you decide to firmly establish yourself as an IT consultant or go in a different direction and work for an employer, these steps are essential for reinventing your professional self.

 1. Assess and analyze your marketable, transferable skills – from all the different areas of your life. Include the obvious skills (in your case, IT) and then dig deeper. If there are things you do as a volunteer in your community, identify, operationalize, and quantify them. Get specific about the results you achieve. They’re the same skills that employers look for, just in a different wrapper. Don’t be modest – count your hard work and accomplishments, even if you don’t get paid for them. (When it comes time to revamp your resume, if you’re spending more than a few hours per week on any given endeavor, add it as part of your professional experience. It’s essentially a job to you, and you treat it like a pro, so give yourself credit for it!)

2. Once you’ve inventoried your marketable skills, you should have a sense of your talent toolkit or core competencies or insertjargonofchoicehere. Figure out the way those things hang together. There are going to be common themes running throughout. For example, even if you’ve never held the title Project Manager, there’s a pretty good chance that you have a collection of skills that line up really well with that role. Now that you have a sense of the emerging themes, you can back your way into various fields that want those capabilities. Of course it depends on what you enjoy and legitimately want to do, as well as what will pay you what you’re worth.

3. Explore & research! As you identify those fields of interest, start connecting with people, new and old, and setting up informational meetings. Learn what you can about possible paths of interest. Investigate the market and figure out the local landscape. Who are the employers in your area that you’d actually want to work for? What kinds of people do they employ? Are they in a position to do any hiring or would it make sense to pitch yourself as a consultant/contractor? Move away from simply checking job boards and do some sleuthing about the companies. See who’s won “Best Employer” awards. Look for press releases about big, exciting projects. Read the dirt on Glassdoor. Talk to people about their experiences as an employee of a company. Get the scoop!

4. Whittle the vast possibilities down to a short list of 2-3 options. Don’t get stuck on finding THE ONE CORRECT ANSWER. For most people, it doesn’t exist. There are likely several things you could do professionally and very much enjoy. And that’s okay. Pursuing a few different options in the short term will allow you to test the waters. If you notice that one thing keeps falling into place while you really struggle with another, that’s a good indicator of which way to go. There’s nothing wrong with throwing things at the wall to see what sticks.

5. Start to rebrand yourself. Update your resume to reflect where you want to go, not where you’ve been. Change your headline and profile content on LinkedIn. When you meet someone new, lead with what’s next for you. There’s a world of difference between, “I’ve been an IT guy but I’m tired of that and looking for something else,” and “After years of building skills across disciplines, I’m now focused on Project Management for high-tech and creative industries.” Both are true, but only one is going to further your transformation.

6. Network. Connect. Talk to people. This is true for everyone, but it’s pretty much impossible to reinvent yourself without a support system of people to help you. A shiny new resume isn’t going to be enough. Your connections are critical. Relationships trump everything else.

(Actually, this point is probably going to be my answer to most questions I ever get. Maybe I’ll just copy+paste it from now on.)

7. Bite the bullet and start trying to get a gig in your desired field(s). It can be part-time, freelance, or volunteer – you don’t have to make a major commitment. So many clients want to contemplate these big picture issues for a long time before taking action. Spending time doing research and soul-searching is important, but only to a point. You cannot meditate your way into a career. The way to find out if you like something is by doing it. And then either you’ll realize that you like it and want to keep doing it, or that it’s not for you and you can move on to something else.

8. Rinse & repeat. As many times as necessary. Keep moving forward. Keep developing. Try new things. Stretch. Grow. What else are you going to do with your time here?



End note: After I wrote the above response, I had a phone consultation with the IT guy. Turned out he was really interested in being a consultant but was stuck on how to get started and worried about all the pieces he needed to have in place before he could consider himself a business of one. We chatted for a while and I let him know that he was much closer to being a successful solopreneur than he realized. There were a few practical factors he needed to consider, but he was essentially already doing it. And by pursuing that type of freelance work, he could continue to work on artistic projects in his community, on his own schedule.



Do you have a career question you’d like me to address? If so, feel free to post it in the comments section below or email it to If it’s a topic that comes up often, I may turn it into a future blog post, but all your identifying information will be removed. 

Written by Kim Eisenberg

Kim Eisenberg

I provide individual and corporate career development services to clients throughout the US. I’m your trusted business advisor, motivational speaker, professional butt-kicker, and complacency crusher rolled into one.

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