What Went Wrong With My Career?

Robin Roecker / Unsplash

It’s taken about a year but I have finally reconciled myself to the position that my need to leave law after working so hard for eight years is not indicative of a catastrophic failure and my previous investments in my legal training and education – including that painfully expensive Masters in the US and those months at my desk that time has forgotten – were not a complete waste.

As I scratch my head and think about what I’m going to do next it seems like a good time to consider what went wrong the first time around. I want to avoid doing the same thing all over again and maybe help you avoid the same.

I suppose it all started when I was 17 and my parents tried to persuade/force me to study medicine at university. I have since learned that they have rewritten history in their minds when they spoke recently of their unfailing support for my decision to study Philosophy, Politics and Economics.  Any support they showed was in the form of visible relief that I wasn’t following through with my threat to study Classics or Chemistry. What do people who study those degrees end up doing?, they asked at the time. [Ironically, it seems that many go on to become lawyers.]

One plus point for Economics was that they knew some fairly respectable people whose children were economists working as bankers for JPM and Morgan Stanley and the like. Those children had BMWs. This was promising.

You see my parents only wanted the best for me, all the opportunities that they didn’t have growing up in a Third World country. And they sacrificed everything to make sure I got those opportunities. They also firmly and unshakably believed that I could, and would, be successful at whatever I turned my hand to.

I’m all for supporting aspirations but, in hindsight, these encouragements probably served to fuel a directionless self-importance. I thought, had been led to believe in fact, that I was destined for something a bit special. It turned out later that when they said “you can do anything”, what they meant was doctor, accountant or engineer.

This may have been when it started to go wrong.

Then at university, surrounded by overachievers, I wasn’t the only one to enter and leave higher education without the faintest clue of what I wanted to make of myself. I had bracketed myself on all sides because how could I take just any job when there was so much potential? This resulted in a kind of career paralysis. I went into auto-mode.

I attended an interview at one of the most prestigious law firms in the country not because I heard some kind of calling but because someone else told me that they were gutted not to have been called, from which piece of information I gathered that this might be something worth going down to London for. I chose between three law firm jobs I was offered after university based not on reputation (although they were all good) but on the social life and in the end followed the choice of my new housemates. It didn’t occur to me that the opportunity to put off further interviews for four years was a poor reason to choose a career.

I never intended to stay as a lawyer. I thought I’d get a professional degree because then I could do that elusive “anything I want” (it turns out you can also “do anything you want” either by doing that thing directly or via doing almost anything else that you want, particularly if you like and are good at it, but this was another thing that didn’t occur to me at the time).

Plus “lawyer, well that wasn’t so far from “doctor”. Maybe my Dad would stop introducing me at family gatherings as his eldest daughter who “isn’t a doctor but at least she went to Oxford”.

Maybe this was also when things went a bit wrong.

It turns out my parent’s weren’t much impressed with my job as a solicitor in the City. Much better to have been a barrister, they said. I worked too hard for what I got paid in their view, and mine too. And what work? “Did I really go to law school for this?”, was the constant refrain of fellow trainees trying to figure out how to use the fax machine at ten o’clock at night.

This is when I realised for the first time that things had actually gone wrong. I persuaded my boyfriend to quit his job and come traveling with me. This was possibly the most sensible thing I had done since leaving school, although alas it was not the beginning of a trend.

Old habits die hard and I didn’t seriously allow myself to imagine a new life off the conveyor belt. I lined up my Masters program at the end of our gap year and we moved to Washington, DC. I continued to search, like a missile, like a detective, for alternative career paths within law – at the World Bank then with the government. In my lifelong game of hot-or-cold, I felt like I was getting warmer.

I was then offered a job back in the UK as a referendaire at the Competition Appeal Tribunal – very prestigious, very well-regarded, and lots of career options afterwards — but in the end I fell for a different siren of vanity: money. What a fool!

I took a job with an American law firm paying one and a half times the salary at a British firm, and so began the worst, most depressing, most demoralizing and most desperate three months of my professional career. I was looking to get out almost as soon as I stepped through the door, and I was lucky enough to be able to do so even before my probation period had ended.

I managed to get yet another job at yet another top tier law firm, one of the best competition law practices in the world in fact. My boyfriend became my husband and everything seemed to settle down. Without even consciously deciding it, I had found myself back in private practice (which is why you should never say never, and also never burn bridges). In fact I was pretty much back where I had started, just a bit further down the road.

The days, weeks and months slipped by and I couldn’t shake the feeling that something had gone very wrong (for real this time). Great work, great colleagues, great clients. It was difficult during those days to see quite what was missing.

Of course in the cab ride from the office at 3am it was easy to focus on the immediate, the obvious – the lack of sleep, the lack of personal time. But what about professionally? I had tried everything – public sector, private sector, international, domestic. I was a good competition lawyer and I really enjoyed the work (most days). If this wasn’t working out, what was left?

That’s when I realised what had gone wrong. It wasn’t a wake up in the middle of the night, “Aha!” moment. It was more like that initial flickering as your turn on a light bulb and the filament begins to warm up.

I had been blindly moving forward making incremental improvements on my situation but never pausing to take a look at the big picture. I would choose between Job A and Job B, systematically weighing up the pros and cons, considering my options, but only ever focusing on the things right in front of me. Finally, at Dan’s prompting, I took a much-needed and long-overdue step back and this is what I saw.

I liked competition law – hence the Masters – and within competition law, I liked private practice. But the big picture revealed that this was a choice of necessity, the answer to the question “what kind of lawyer do you want to be?”. Not since I was 20 had I lingered on the question “do I want to be a lawyer?”. And when I finally got around to doing just this at the age of 29 the answer that came back from deep within was – no. Bugger.

There are plenty of good questions that came after that realisation. What next? [Still figuring that out.] Was it all a horrible mistake, a colossal waste of time? [I don’t think so.] But the question that really matters now is: how can I stop myself from doing this again?

You see what I want to do next is to start a business and this is definitely another thing I could get carried away with. I don’t want to find myself in 10 years’ time with a decade having been swept away in another tidal wave of A vs B choices at the micro-level (should I start this business or that business?), having missed the big picture entirely (what do I want to do with my time? what kind of life do I want to lead?).

I think the most useful advice I have come across to help with avoiding this pitfall comes from Lean In written by Sheryl Sandberg, the COO of Facebook. She suggests that we should all keep in mind two goals: an 18-month plan and a long term dream.

She says 18 months because it’s longer than a year so it’s a real amount of time in which you can actually get something done, but it’s not as daunting as two years which, if you’re anything like me, is a horizon beyond which time cannot properly be measured or imagined. But then you should also have a long term goal, the purpose of which is to keep you honest, to keep you on message.

This is the piece that I was missing before. If you asked me when I was younger what I wanted to be I might have said that my long term goal was to be “successful” (after all, that’s exactly what I had been told I would be). This is actually meaningless without a reference point – successful at what? – and pretty unhelpful even with a reference point. It doesn’t inform my current decisions because it can’t act as a guidepost or litmus test for my current activities. How do I know if what I am doing is working towards being “successful”? How can I measure whether this or that opportunity is in the same direction as “successful”?

The economists in the crowd channeling John Maynard Keynes may heckle “in the long run we are all dead”. In other words, what’s the point of a long term goal – it lies in a point of time at which you never arrive. But in fact what Keynes meant by this statement was that you better sort out the now because otherwise the future you long for will not come. He saw on a macro scale exactly what I see on the micro. There is no point dreaming of some future if you are not looking after the present in a way that is consistent with that vision.

I have learned that if you live without the guiding compass of a long-term goal then you are at risk of losing all bearings. Goldfish can’t conceive of the future but we can, so we should use this astounding ability to inform our current decisions.

So here it goes, my first real stab at avoiding Small Picture Syndrome with my 18 month and long-term goals (no laughing please).

18 months: publish my novel, start a business, move house, buy a flat.

Long-term: work remotely on a variety of cool projects from a house with panoramic views of the sea, probably in Scotland, where Dan and I raise our family and dog(s) and grow our own food while he makes furniture.

Now maybe neither of these visions will come to pass but, man does it feel good to put them down on paper, to memorialize this state of mind and this, perhaps temporary, configuration of my preferences. I can only hope that  having them at the forefront of my mind helps me make better decisions day-to-day.

Now please excuse me – I have a novel to finish and I also need to learn how to grow vegetables.

What would your 18-month and long term goals be? Or do you think having a plan is too restrictive? Join the conversation on Twitter @MichMeagher.

Love links, hate distractions. Now that you’re done, here are some internet bits to put this article in context:

Lean In: Women, Work, and the Will to Lead is a fantastic book pulling together some very compelling research and insights from Sheryl Sandberg on how women can make the most out of their careers and how men are part of that story. I will be writing more about this book. A lot more.

See this post by Simon Taylor, a professor at Cambridge Judge Business School on The true meaning of “In the long run we are all dead”.


37 thoughts on “What Went Wrong With My Career?

  1. Hi Michelle. I read your post and there have been a lot of parallels to my life except for everything has been a little less extreme for me – only one of my parents was constantly suggesting medicine, I did the Oxford IP course and not a masters and I’ve always worked for a large national firm so post-8pm finishes have thankfully been rare.

    I have a great life, enjoy my work and live in an amazing city (Bristol). Yet recently I have been struggling with whether law is really what I want. In my situation I don’t necessarily think I’ve gone wrong anywhere as I think I’ve made some good choices (doing law, national over city firm, moving to Bristol). I’ve also been helped along by a few huge doses of good luck, which have set me up well for whatever I might want to do now. I’m also worried about just quitting and then doing the whole A v B choice thing (I have a few ideas) plus also just quitting generally when I have quite a good thing going.

    It would be great to meet with someone who has been through all of this to talk to them about their experience and how they dealt with it all as I just keep reading things like your blog on the internet making it always feel like the escape is for other people who are different to me. If you are still in the city and would be willing to chat over a coffee I’d be very grateful for an hour or so of your time. Just let me know and I can PM you my contact details (unless you see my email address because of this post).

    • Hi Chris! I think the most important thing is to ask yourself what the source of your doubts is. It sounds like you quite like your job so it would be interesting to hear what makes you think law isn’t for you. I know for a lot of my friends it’s that the job hasn’t turned out to be what we imagined when we were 20 – indeed I think the profession has changed dramatically over the last decade.

      I think for lots of people leaving a career is truly an escape – and it is bold and commendable when people follow their hearts. But it can make others worry they don’t have what it takes to do it which is not true – anyone can do it, you really just have to want it.

      I’d be more than happy to talk to you about my experiences. I’m not in the City anymore but will send you a PM to work something out!

      On Thursday, 6 March 2014, workerbeefree wrote:


  2. This was a really good post, and as I work in a role that seems perfect on paper in a role that I was aiming for, I don’t feel the content I thought I would. I’ve also read Lean In and really like the insights. I like your suggestion from the book to consider 18 month and long-term goals. And I’m happy for that you are able to figure out what that means for you now.

  3. Michelle – thank you for a beautifully written piece. You capture perfectly the wake up call that comes when we pause to look at the big picture, and your question ‘what kind of life do I want to lead?’, is the key one. I am aware that sometimes people jump out of busy jobs with difficult bosses, only to create a new life of busy self employment with difficult clients which is equally unsatisfying to them. It’s so important to ask how we want our lives to be, what serves us and nourishes us. I’m excited to keep reading your posts and wish you every success with your novel. Nicola (www.claritycareers.co.uk)

    • Thanks Nicola! I am so keenly aware of the risk of being my own worst boss and can see there is scope for working even harder and less productively in self-employment than when I had a “proper job”. I’m actually completely reassessing my relationship with my work on lots of different fronts. It’s challenging stuff! Please do share any further nuggets of wisdom – I know I could do with more insight.

      On Fri, Mar 7, 2014 at 9:48 AM, workerbeefree wrote:


      • I would recommend three very good books: The Work you Were Born To Do by Nick Williams, A Life at Work by Thomas Moore and Working Identity by Herminia Ibarra. Where I start with career change clients is get really clear about your values and let those guide you in your career transition. I very much empathise with all the comments on here, regarding the challenges of changing from a well paid job to do something new. In reality, for many it often requires a period of transition, training and building up new networks whilst retaining some income from the field where they are known. The good news is many people do make the change and are delighted that they did.

  4. Great piece Michelle, very enjoyable. I come from a similar headspace and have self-published some work since leaving a ‘sensible’ career.

    I look forward to updates on your novel, as this post is written beautifully.

    Good luck with everything, sounds like you have a wonderful time ahead of you.


  5. Hi Michelle,

    I found this a really interesting blog and certainly this is an issue I know many people our age are grappling with. I went down a very similar path, Law and the BVC, since it seemed the ‘right’ thing to do… I then spent nearly seven years in the military before leaving last year. The crux for me was that I realised I’d stopped enjoying what I’d set out to do. As well, I’d stopped feeling passionate about my work and I could feel myself becoming hard-nosed and bitter. I made the very scary decision to leave and haven’t looked back. I’m now in a job I absolutely love. I still haven’t got the long term plan worked out, but something I read the other day really made me sit up and I’m working out how to achieve it. It is:

    ‘To know that one life has breathed easier because you have lived.’

    This has really resonated with me. So in summary, my advice, reach out, talk to as many people as possible, ask questions and I think you’ll be amazed where it takes you.

    Good luck


    • Thanks so much for this comment Rachel and for sharing your experience. I had definitely stopped enjoying what I was doing and I wonder how much I ever really enjoyed it except in a very cerebral and abstract way.

      I’d love to know how you found the job you now love (and congratulations on doing so!).

      I really like the quote and it goes to the idea of personal growth being intimately linked to what you contribute to the world which I’ve read a lot about from The Minimalists (although have yet to really put into practice). I wonder whether making the world a better place for other people comes from the work you do or whether it comes from just living in a happy and considerate and supportive way? Maybe you need the right kind of job that puts you in a frame of mind that allows you to help other people to breathe easier, whether or not the job itself involves “helping people” in the traditional sense.

      • Michelle,

        It was great to read your reply. After I had signed off from the military, I was utterly bereft as I realised something that I had loved for so long was coming to an end, but also and more importantly that it wasn’t working for me any more. (The analogy between leaving the forces and the end of a marriage wasn’t too far off the mark…!) In any event, what helped me was a really in depth analysis of myself – strengths, weaknesses, want and needs, versus what was out there and how to get the best fit between the two. I realised that I’d actually really enjoyed what I’d done for the past 6 1/2 years, which was people, their development, variety, adventure, travel and my own development as an individual. I initially thought that Learning and Development (L&D) within an O&G or mining environment would tick most of the boxes. However, I certainly felt that the best was behind me and that I would have to accept a grey corporate type role. You do not have to ‘accept’ anything if you can be flexible. And that is key. In August last year, I left the UK with three bags and moved to Dubai to work for the FCO in L&D. I travel 50% of the time, ironically to the Embassies that no one else wanted to go to, but which I think are awesome, delivering advice, help and support to some incredible people. I don’t get paid that much, I live in a shared flat with 7 other girls and I’m perpetually jet lagged, but I’ve never been happier.

        I think the points you made above were very insightful. Perhaps ‘breathing easier’ is very much open to your own interpretation? I certainly don’t feel the need to rush off to medical school. And maybe you’re right, perhaps it is in the little acts we do every day, a state of mind, rather than a vocation?

        Still, lots to think about…my next thoughts would be these:

        – There’s two great books I read to help me decide; What colour is your parachute? and The Decision Book.
        – You still need to earn a crust, so can you take the experience you’ve gained thus far and align it elsewhere? Law publishing? Law teaching? Something like that, but which has a different outlet for your skills and energy?
        – Have you considered doing something like MBTI? The Myers Briggs Type Indicator is a fantastic tool for many things, but can also be used to guide an individual in choosing a career that suits their personality. (Annoyingly my personality suits the Law and military…)
        – Can you get yourself a coach or someone who can help guide you through this thought process? Coaching, if done well, can be incredibly powerful in helping you find the answers. This can be a trusted, but frank friend, certainly don’t pay for it!
        – You will go down many wrong paths and (probably) make more mistakes, but keep asking questions of yourself and others, stay curious and don’t give up.


  6. Hi Michelle,

    I absolutely agree with what you have said. I went for the best just because some people back home told me that I was never going to make it in London. But now thinking whether it was good at all, I am not sure.

    Good luck with your novel.


    • Thanks Valentina! I think it’s even harder to deal with the expectations of people who haven’t actually been through the system you are going through. I know for my parents they were disappointed I chose the law firm I did because it wasn’t the one firm in the country they had actually heard of. Not necessarily the best way to make decisions about your career!

  7. Hi Michelle – nice post! I also studied PPE at Oxford, then went into City law, disliked my time at a US firm from day 1 (but haven’t managed to make as speedy exit as you!). I am swaying between looking for a more interesting area of law (I’m in corporate – awful hours) at a friendlier firm or trying something totally different.

    Your post makes me think that sticking with law and finding a better option would improve things in the short term but ultimately I also don’t feel fulfilled by law, so maybe it would be better taking the leap now to something new. It takes guts though – well done.

    I look forward to reading more of your posts!

  8. Hi Laura! I guess where I’ve gotten to is thinking that at a minimum we should be doing something that interests us and leaves room to LIVE, even if that is by putting up some boundaries in a demanding environment like City law (some people do have a life, I believe it’s possible!). And maybe staying in law moves you towards your long term plans – whatever they may be. But I think the breakthrough point for me was realising that these are really important questions that deserved to be thought about now rather than later, even if it’s kind of exhausting just staying afloat sometimes.

  9. Thanks for such an honest and self-aware post! I read this at just the right time. I too am an Oxford educated City lawyer and pretty dissatisfied with my working life. However, I have a little boy to look after and I am the main breadwinner in our family, so making these decisions is pretty tough when you know you’re the one who has to pay most of the mortgage each month. But there are glimmers of light in my situation too. Over the last year I have been involved in THE most amazing voluntary project outside of work, plus it looks like, come the summer, there may no longer be a job for me at my firm. So maybe I will be forced to make some changes and sometimes having your hand forced is a good thing. Thanks again for the post!

    • Hi LondonGirl – your comment has made me realise that I am pretty lucky to still be able to make what are essentially pretty selfish decisions about my future, although one of the things that drove me to make the changes I have was that I do want a family one day and I want my kids to be inspired by my attitude to life. I don’t know – it’s easy to think about these things when you don’t pay the mortgage, although that is one of the big reasons we haven’t taken on a mortgage yet – we ended up valuing the freedom more than the dream house. But then that’s just another tradeoff.

      I’m sure you’ve heard it before but one thing that always sticks with me when I think about my career and having kids is the apocryphal story about the mother saying to her child “I had a dream once, and then I had you”. I think my mother gave up so much for me, maybe too much, and I worry that that means she relies on me for a lot of her life’s fulfillment, which is a lot for any child to bear.

  10. Michelle, as you say, it’s all about seeking out the right balance and deciding what trade offs you’re happy with. I know my little boy will benefit hugely from seeing him Mum happy with her work, motivated and enjoying life, just as long as he has a roof over his head, food on the table and new shoes when he has grown out of the old ones! When we bought our house in London, we knew that I would not necessarily be in my job forever so we were careful not to stretch ourselves too much with the mortgage and knew that with some careful planning and sacrifices I would be able to do some different at some stage if I wanted to, and we’re still in that place. We never committed to private schooling or anything like that, The really tough one is the cost of childcare. It is so expensive here that you have to earning a certain amount to justify (financially, that is,) working at all, or you need a partner who is able and willing to subsidise the cost of the childcare so that you can do something that earns you less than what you pay out in childcare every month but which brings other benefits – enjoyment, marking your place in the workforce etc. All v difficult to balance! I would love to have a second child, but the ramifications terrify me.

    • When you explain it like that I can really see what the Childcare Trap means. It strikes me that as a society we are putting parents in an impossible position. What has made the cost of childcare so high? Has supply (good, reliable, safe supply) not kept up with increased demand from more women going back to work sooner?

      • Something definitely needs to change. I don’t have the solution unfortunately but if I did I’d be starting a business right now! The irony is that it costs parents a small fortune, yet many nursery workers get paid no more than minimum wage. I am happy to pay to ensure the people looking after my son are well paid for their work – they’re looking after my boy after all! But it cannot cost the earth as it does at the moment. I live in South East London and he goes to a good local nursery. It costs just over £1k a month. I do not understand how, say, a single parent on an average London salary would be able to afford that. There is some help there – plenty of employers offer childcare vouchers that are deducted from your gross salary, and once a child is 3 you get an early years grant from the government that reduces the bill by maybe £100 – £150 a month. Good, reliable, safe and flexible childcare is the thing that would make most difference to the lives of working parents, or at least to those not fortunate enough to have family nearby who are able and willing to help look after children.

  11. Rachel – you have given me a lot to think about! I have read Parachute but will also check out Decision and the other resources you listed! My current thinking is that there is so much more out there that I would feel more passionate about than law, but I try never to burn bridges and I can’t get away from the fact that I find competition law fascinating as a subject!

  12. Michelle,

    I liked very much your honest and clear-thinking blog, which one of my best friends just forwarded on to me.

    I’m 32 years old and last month canned a good job as an investor in commercial real estate to start a business.

    I didn’t hate my job; it was quite lucrative, very social, intellectually satisfying and the hours were manageable. However it was ‘just a job’ and my dream has always been to start a business. I went through the process in my 20s of making “incremental improvements” to my job situation by moving firms and moving within firms, but still it wasn’t enough.

    As a sit with a blinking cursor working on business ideas to test against my friends and former colleagues, i’m half-excited, half-terrified. But you only live once and one has to follow one’s dreams. One has to try.

    My parents think I’m insane and my relationship with my Dad is stormy at best, painful at worst. He was a corporate lawyer for 40 years and believes – in a rather Japanese fashion – that one should be ‘grateful’ for a respectable FTSE job with a good pension. After all, what more could one want? A lot, as it turns out.

    So over the next 18 months i’m going to start a business. If it works out, i’ll live by the sea in 10 years time in a big house. And if it doesn’t, i’ll live by the sea in 10 years time in a smaller house.

    • Hi Andrew – the “you only live once bit” is the part that made me make the leap, and it’s also the thought that keeps me going. I am scared, I am a bit confused, and I have a million ideas for projects floating round my head at any one time. But ultimately I know that wherever this path takes me it is a path of my own choosing, one that I have actively engaged with and I know longer feel like I am being swept along by the crowd. It’s pretty exhilarating and it’s so good to hear from others taking the same journey.

      Lots of people in these comments and on Twitter seem to be saying they are at the beginning of a similar transition. Is there anywhere where people can meet socially to talk about this stuff? Not in a networky way, more like support and laughs and ideas?

  13. Michelle,

    A couple of my friends go to the ‘Escape the City’ events and say they are a lot of fun.
    I’m getting the best support from a friend of mine who is at exactly the same stage as me in setting up another business – we share the same excitements and fears, and we chew these over once a week over coffee. I find older / semi-retired successful businessmen provide tremendous support and are excellent sounding boards – they are generous with their time, encouraging yet measured, help one think through the thorny issues. The small number of 30-something millionaires i’ve met just say “do it”, which is inspiring but one must beware the rose-tinted spectacles of those who hit the jackpot at the first attempt!!


  14. This article came to me at such perfect timing that I even got goosebumps reading it! I have had the same ‘problem’ of parents wanting me to be extremely successful and never being content with any of my life choices. I took a different road to yours: I threw myself into dream when I finished uni, telling myself ‘It’s either now or never’. It hasn’t been easy and i still have doubts about whether it was a good idea ;) but life is all about learning and growing. good luck with your novel!

    • I have a huge respect for people who take the “risky” path straight out of uni (with hindsight I realise that there was more risk in the path I took = lost years). Also love your concept of a light bag. I used to dream of something I called The Lightening Project – a way to live a lighter life. I recently came back to those thoughts when I got into the Minimalists blog. I’ve moved a lot over the years and that has always helped me streamline my possessions but have been in the same place for almost three years now and the stuff has accumulated. Part of changing career and lifestyle is acknowledging what kind of lifestyle we want to lead and the “lighter” that life is the less we rely on money etc to turn it into a reality. Best of luck in your journey!

      • Thank you very much! I’m glad you find happiness in lightness and simplicity. All the best in finding the lifestyle that suits you most.

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