Seven Lessons I’ve Learned From Making Unconventional Career Choices

unconventional career choices
Do not go where the path may lead, go instead where there is no path and leave a trail.
– Ralph Waldo Emerson

It took me nearly 18 months to land my first full-time job…and less than two months to quit it.

I knew how silly my decision seemed to the people who cared about me. But I also knew that not only was I miserable, I wasn’t moving closer to my goals. My dream was to be a journalist, and this position was marketing, not media.

That was 12 years ago, and I’ve been freelancing ever since.

Most of that time has been wonderful. I’ve met fascinating people, learned endlessly, and been able to share what I’ve learned. But somewhere along the way, without even realizing it, I fell into a rut. It was a comfortable rut… but I no longer felt excited about my work. I wasn’t telling the stories I was passionate about.

I knew I had to make changes.

I’m always meeting the most amazing and quirky people in the most unlikely places— I wanted to tell their stories. Now I am. But to do that, I’ve had to make some unconventional choices for someone in their mid-30s.

Here are the seven most invaluable lessons I’ve learned so far:

1. Make choices based on your own values, not other people’s

We all have different priorities. For me, flexibility and creative control take precedence over security. For other people stability and a consistent, reliable income may be worth sacrificing some autonomy for. Being an extrovert, I like to talk through my choices. But it’s important to remember that even the most well-meaning friends tend to advise according to their own values.

2. Be careful who you vent to or seek advice from

It’s good to get different perspectives, but often the people who care about you most will encourage fear-based decisions. A dear friend of mine often mentions retirement issues and reminds me that I should be earning and saving more for later. She may be right, and I know she genuinely cares about my well-being. But worrying about that will not help me achieve my current goals.

3. Put yourself in a supportive environment

You don’t have to sequester yourself off from everyone who doesn’t think you’re making the right choice, but try to counteract negativity with positive voices. When I transitioned from a combo of part-time work and freelancing to full-time freelance work, I wrote a story on that very topic for a national newspaper. Interviewing people who had successfully made the same transition provided me with a more balanced perspective, lots of encouragement, and the opportunity to learn from others’ mistakes.

Making a big career change can be stressful, and it’s easy to become down if the process moves more gradually than you’d like. Don’t give up your social life.  Surround yourself with people who will encourage you to press on. Find online communities.

4. Accept help

Making changes requires support. This year I decided to reduce my paying workload so I could devote more time and energy to creative projects. To do that, I rented out my flat and moved in with close friends in another state who have four young kids under the age of 6. That has been the most humbling help I’ve accepted… Other friends have helped with networking, brainstorming, and editing…You can’t do everything on your own. Be grateful and look for ways to give back, but don’t be afraid to accept help.

5. Don’t close yourself off from opportunities

Sometimes a request seems so unlikely to be granted that we are too afraid to ask. Do it anyway. Be confident. Be polite. But ask. I’ve won scholarships and awards I didn’t think I was qualified for. I’ve gained entrance to conferences that were sold out for months and been granted media passes that I was 99% sure I would be denied. If the worst potential outcome is a bruised ego or a simple no, you’ll cope.

6. Give yourself time

I struggle the most with this one, and it’s getting harder as I get older. I feel self-conscious that I should have my career sorted by now. Sometimes I just get impatient or find myself responding in a prickly manner when someone innocently asks how it’s all going. But it’s my issue, not theirs. Big changes take time… sometimes a long time.

7. Let yourself be uncomfortable

It can be stressful taking creative or other types of risks and not knowing whether you’ll get the outcome you hope for.

Learn to see uncertainty as opportunity…even if it is uncomfortable at times!

49 thoughts on “Seven Lessons I’ve Learned From Making Unconventional Career Choices”

  1. Excellent advice there Lynnette, I too was stuck in a rut some 10 years ago. A half hour chat with a hypnotherapist set me on the path to changing my life 180 degrees in just 2 months. When I look back at my career I see that every step was necessary, but eventually working the way I wanted, at what I wanted, in the way I wanted, was the only way to be truly happy. I haven’t looked back since, even though times have still been tough here and there. :)

    1. Wow, isn’t it crazy how change sometimes takes so long to get started, but you get the right catalyst and it becomes unstoppable? So glad you found a path that makes you happier. And yeah, I think we all still experience tough patches, just not everyone admits it:)

      1. Isn’t it odd how some life changes make a huge difference in your focus? I have been a journalist (mostly radio) almost all of my life. Now I am writing part-time for a local magazine (fortunately, we don’t need the money, I just need to write.) But poems, as bad as they may be, come and they compel me. They wake me at 2- 3 a.m. So I get up and write, or they fly away. Years since I wrote poems, not since college. Many have been inspired by a friend’s nature photographs, and we are discussing a “coffee table” book. Good project, I think, and we will shop it around.

  2. Lynnette – I hope you remember to pat yourself on the back every once in a while because you are awesome.

    I took my leap into a career as a Hypnotherapist when I was 45. If could go back and talk to my younger self, I would tell her not worry so much. Everything works out fine.

    If I may, I’d like to add a #8 to your list:

    Train your mind to shift your negative thoughts into positive and KEEP FOCUSING ON WHAT YOU WANT. You’ll always feel better in the moment and you’ll keep yourself open up to opportunities that you would never see while stuck in the negative.
    (This one is so important that I teach it to all my clients and even published a book about it. I call it “Powerful Thinking.”)

    I hope to read more from you, Lynnette!

    1. Thank you Wendy, great addition, focusing on the positive makes SUCH a difference. Reading your comment made me realise that for me, most of my negative thoughts are sparked from comments other people say and not so much from within myself, which is reflected in my list– but I completely forgot that for many, many people that isn’t the case.
      And yeah, I’d tell the younger me to chill a bit too:)

      1. You’re right. Most people create their own negative thoughts and then find others to prove that these thoughts must be true and real. Then they give up.

        It’s a vicious cycle but it can go away when when you realize that you can take ownership of the fact that you have the power to change your thoughts.

        Jim Rohm once said that “we are the average of the five people we hang out with the most.” How true!

  3. I enjoyed this, Lynette…a lot. In the 21st century it becomes easier to make different choices than in the past. I like that you’re not locked into the box of a certain income and lifestyle…because your ego isn’t tied up in numbers or status. Great post!

    1. Thank you for your kind words! You are right, we definitely have opportunities other generations did not. I sometimes wonder if life would have been less stressful and we would have been more content in another century, but I’ve never been much of a conformist, so I kind of doubt it I would have been as fulfilled in a role all laid out for me:)

  4. Lynnette,

    Very thoughtful and personal post. Question: Which of these lessons do you feel are most accessible to various personality types? Ex: Lesson 1 may be (emphasis on ‘may’) be more difficult for extroverts while coming much more naturally to introverts. Would love a follow up post on how different people you know with different personal OS have adapted these ideas to their own life. Keep writing! #storiesmatter

    1. It’s an interesting question Sergio, will have to think/research more about it. My hunch is that the pressure and/or tendency to make choices based on other peoples’ values, whether broader societal values or the values of those close to you, isn’t linked to extroversion or introversion. Extroverts may hear about it more overtly because we bring it up more, and people-pleaser personality types may be more likely to bend?
      Definitely an interesting topic to consider more…will see what I can find:) I should have ended with a question– what lessons have other people learned? That might help in the research:) If anyone wants to add any, I’d love to hear them:)

      1. Introvert here- I find that my reaction/concern for how my decisions are perceived by people is influenced mostly by a combination of my current opinion of how much ive accomplished lately, and what that specific person means to me.

        If i sense that they don’t even share the same ideas about accomplishments as i do, then i feel vulnerable, but more so if they are close to me (friend, family, mentor)

        In a funny way, i first found it easier to be gracious with strangers who didn’t understand agree what i’m trying to do with my life. With strangers, i was less influenced, i could be less sensitive to their opinions, and not lose my positive outlook. I have had to carry that over to people i am closer to, and that has really helped.

        as much as relationships matter, we all deserve a private part of ourselves devoted to our dreams and aspirations, a part that no one can dent, no matter who they are, not even ourselves.

  5. Thanks for the thought provoking post Lynnette. It’s intriguing to read and think about lives

    and choices which appear to be so free. I am wondering though, how individual our

    choices and values really are when we are surrounded by the influences of our society,

    family, friends and so on.

    I’m also interested in Sergio’s suggestion about personality types and the influence this

    has on how easily individuals may apply these rules to their own lives. Looking forward to

    comment on that idea.

  6. I guess it’s a philosophical debate, but I personally think regardless of the influences around us, the choice is still mostly ours. {I hate speaking in absolutes!!}. I think our personalities make us more vulnerable to different challenges, or more likely to respond in certain ways, but I also believe there is a fair amount of universality to much of this especially the underlying theme of ‘To thine own self be true.’ Who among us has never struggled with that? But I agree would love to hear differing opinions:)

  7. A very interesting article Lynette, thank you. I’ve successfully switched careers a few times and had to apply all of your points to see the changes through to the end. I would add that the only “approval” or “permission” you need your own… waiting for the approval of someone else is the kiss of death, you just have to believe in your own abilities to learn, cope and thrive.

  8. Well said Lorna. I agree! That kind of confidence really helps! Although I do think that even when you possess that confidence and have chosen your path, other people’s negativity can still be discouraging.

  9. Berat Seçkin Demirok

    I like ”lesson 7” most. Yeah, life begins at the end of our comfort zones. Thank you very much, it is very inspiring.

  10. Awwww… Look at you, Lynnette, responding to everybody… So sweet! Just wanted to affirm those truths and say thank you :) I’ve struggled with those issues a long time…seen others struggle… And I will pass this along, for sure. Keep up the clarity!

    1. Trying to, anyway…though not all the facebook comments!! I once heard an interview with Ani Difranco, in which she discussed universal vs personal, and her belief that as people we have way more in common than we often admit… it stuck with me:)

      1. I’ll try to say this succinctly… People who think they have more in common, DO …with people who think they have more in common. And people who do not think so, have more in common with those who do not think so. Yet, so often neither is correct, as well. LOL

  11. Thanks for sharing the lessons you learned. I think I found number 4 the hardest, I was too ashamed to admit I was struggling. I started my own business and I was trying to do it all on my own.
    Now I have a family friend who is mentoring me and I wish I had let him help ages ago. The progress made after spending a day or two with him has allow me to do more work then I did alone in the last month.
    Ive always loved to do number 7 and throw myself out of my comfort zone and I think its something I will always do.

  12. I’m sending this to my daughter. She’s 23 and has returned to college after a bit of a hiatus. I’ve always told her to find her bliss and all else will be fine…hoping she does with her new choices. Thanks, you are a brave woman.

      1. Thanks…just want them to be content in what they do…I cannot remember who said it but its a mantra to follow,

        “If you love what you do you will never work a day in your life.”

  13. I too feel called to be creative in my career. I want to do more with my life than work in a cubicle all day 40 hours a week, every week, until I have one foot in the grave. I also do not like my life income being subject to office politics and gossips with low self esteem.

    I am investing in my own business. It has not generated income just yet, so far it has been a big investment getting the legal documentation filed, basic business needs, advertisement printing costs etc.

    Most people I know opt for the security of a 8-5 grind. I find your article encouraging and confirming during this time of building the foundation of my business. Thank you.

  14. I enjoyed reading your article, and I am probably one of those who tends to tell people “What about retirement?” as it is suggested you should have $1,000,000 at a minimum in assets when you retire now, But at the same time, I understand feeling free from certain confines. I work in DC, have a nice high-rise apartment, six figure salary in not too much longer…I wish I didn’t need this job, as I am most certainly not very comfortable in a business suit, but I don’t have any talent at anything other than making deals :/

    I’d like to be a special education teacher, but I’m not sure I could justify giving up my benefits I have now (everything from investment options to being allowed to arrive anytime between 6-9am, to the lovely people I work with)

    I quit my well-paying job last year to pursue the special education path, but begrudgingly returned a year later when I couldn’t find work. even just to get me by, let alone keep anything in savings for the future (wedding, kids, post-graduate degree, travel, etc) I am stuck :/ in my case, it will take money to make money- maybe I can start a business in another 10 years or so? I really don’t know what I want other than to be a stay-at-home mom, but until that happens…??

    1. Yeah it’s not an easy choice…maybe you can keep looking while you are still working at your office job, or try to negotiate to work 4 days a week instead of 5 and volunteer at a school on that day?

  15. Truly inspiring article Lynette, especially for me. Decided to make a career change just over a year ago and jeez did I seem crazy to many people. Things are only just beginning to take shape and the sea is still rough but I can now see a future in what I am doing clearly.

    So reading through this article kind of gave me that extra boost.

    Thanks a mil for this brilliant article. :)


  16. The supporting environment thing is BIG. Things are so much easier when you surround yourself with people who are willing to help you and support you. Conversely, get out of environments that are detrimental to your growth, in your career and as a person.

  17. Happenstance is a career theory on how some things just work out or don’t and I have always just felt this way. Sometimes the best thing is to sit with a counsellor and hear you say your dreams, thoughts and fears out loud and then start to process them. Things, people, circumstances, experiences can shape us in our learning journey’s. I’ve recognised small things along the way. It started with NEVER working on my birthday and I realised I don’t do Monday’s, I’m not really a team player and I cannot stand taking no action or change not being communicated properly or change for change sake (but I love change just to clarify). Life events like change and death make us realise HAPPINESS is importance and whilst retirement is to be considered life needs to be lived in the current and we can get so caught up in worrying an focussing on a future that might seem better and brighter but how can it be if we don’t live now (firm believer in ‘you can get hit by a bus tomorrow and what has it all been for’?)..’He who never has a failure, never makes a discovery’ to adapt a fav quote of mine…I’ve dabbled in setting up my own business, it was isolating and taught me things about myself. I’m an ideas person but setting goals and actioning them I may not as I let life get in the way as this also shows me that something stifles my creativity and I should go more into the future with passion and enthusiasm and what will be will be. For now, helping people is a great love so I have become a qualified counsellor -specialising in careers so doing that on a consultancy basis is my aim……I hope we all self-talk more positively and sometimes we have to adapt a little or alot to see the changes we want to. This year also I have held a fund raising event for animals and also assisted an elderly place acquire new pillows by having a local merchandiser donate them…..don’t wait for someone else to do these things….you do it and whilst these things have nothing to do with my career they are the what has mattered someone what most to me and given me the biggest pride.

  18. Brilliant post, thanks for sharing! I love the clarity and assertiveness about how to work to achieve your dreams, but here is a question that we have been talking a lot about with some friends.
    We have been lucky to live in an “easy access” generation were we have had sooooo many options; that sounds great a priori, but in this sea of opportunity some of us are finding it extremely hard to find that driving passion/passions… I love many things, but there is not one (or two, or three… A sensible number to start working with!) that stands out to the point of making me start working with such a level of determination. I’ve seldom wondered if it’s just lack of will power and/or laziness, but I have come to the conclusion that it’s more that, being a subject that creates such anxiety because we don’t know where to start, we just let it hang in the back of our heads and loose chances to get started in the meantime! (plus the stress of whether we will find an answer) I know there is no easy fix and I find that it’s a subject that makes no sense to many who naturally find their true ways, but any suggestions on how to look for true passions are greatly appreciated! Thanks again !

  19. I agree with this article as I’ve done this myself but I would caution people to still consider having some financial security even if it’s a part-time income at a job you love or can tolerate for a while.

    Put away 1-10% of any earnings for an emergency fund/ retirement etc is a good idea. Or your financial burdens while finding yourself may become someone else’s problem. Do your best to achieve dreams while taking care of yourself and your family. 💜

  20. I’ve had the same experience of getting a job I was really excited about, only to leave it a couple months later.

    Now I’m pursuing freelance writing, and have definitely had some (unsolicited) naysayers. Fortunately, I also have supportive friends cheering for me. I’m in a part-time “day job” that I hate, and working on freelancing on the side, but I’m considering quitting even this tiny income to put more time and energy toward building up a freelance career. I’ll consider your story as I make this decision…

Leave a Comment

Your email address will not be published. Required fields are marked *