in entrepreneurship

How to Start Over. (Hint: It’s Never Too Late)

I got an email from a reader last week with the subject line “How to Start Over”. In it, the reader shared his personal story – being about 10 years into his career – balancing life with kids, a family, and a big corporate job – all while trying to establish his own digital platform and business – and feeling like it’s time to break free and change things, but feeling overwhelmed by the idea of “starting over”.

He brought up a point that I’ve been confronted with many times. I wanted to share my response to his email, with one overwhelming preface: You’re never “stuck”. As much as it may feel like you can’t get out of your current situation – as much weight as you put on the importance of maintaining your nine to five – as much fear as you have of disappointing your family – regardless of your current situation and regardless of your age, you’re never ever stuck.

Here was my email response:

“…I think you bring up a point that folks are faced with time and time again. I always share the story of my dad and I playing golf last year. He’s been an accountant for almost 40 years, and he’s always been apathetic to his work and has always told me he’s just “working to retire”. When I asked him why he doesn’t quit and do something else – his response was that he’s been doing what he does for so long, and it just “is what it is” – and that he doesn’t know what else he would do.

Believe me, I can understand the sentiment, and it’s hard to get into something new when you’ve been doing the same old thing for so long. But it was this conversation that inspired me and continues to motivate me to not waste a moment that I have to work on doing what I really WANT to be (and should be) doing. It’s kept me humble and active in continuing to build my business and establish myself professionally.

The best thing I can say is that you’re not stuck. You never are. It’s not easy to break free and do your own thing – especially with the added responsibility of supporting a family – But if I, a 27 year old with not a heck of a lot of experience, can get fired and start a business at age 24 – someone at age 35, or 50, or however old, with a heck of a lot more life and work experience, can certainly do it. It just takes creating a plan of action for yourself – and not being defined by your age, or held back by your current situation.

Take things one step at a time. You don’t have to quit TODAY and go “pursue your passion”. Create a plan. Start working on your passions on the side (it sounds like you already are) – and set yourself up to make an easier transition in the not-too-distant future. It also REALLY helps to set a deadline for yourself – a date to take the leap – and work toward that…”

We’re afraid of disappointing our family. We tell ourselves that we’re not good at anything else except what “we do”. We’re terrified of change. We convince ourselves it’s “too late”.

The only way you’ll be disappointed is if you never try. The only way to know if you can’t do something is if you give it an honest effort. It’s only “too late” when you die.

I hope, if you’re reading this – if you’ve been reading this blog for the past several years, you believe – honestly believe – that you can create whatever you want to create for yourself.

The best thing you can do is to start. And it’s never too late to get started. 

Add Your Voice



  1. Thanks Matt for another great reminder!

    I found, in my job as a Career Counselor, that I have this conversation with 2-3 people (alumni) each week. My job is not to tell them what to do, but to show them what the road could be like (or how to find it out) and I often hear them say “thank you, now I know where to get go next.”

    It’s not easy but I always go back to that whole “impossible is nothing” with the people I work with… it just depends on how you approach it and what will work for you! It can be done!

    • I think you hit the nail on the head. It’s really about embracing possibility. The challenge is that we fall into a way of thinking that tells us that what we REALLY want to be doing isn’t possible – here’s to embracing possibility and allowing ourselves to believe in…ourselves, and what we’re capable of.

  2. Totally agree–There is an infinite distance before us with a plethora of new ideas, desires, adventures, wonders and awes! For me, I have a lucid knowledge of my passions in life, but I become flummoxed when it comes to taking action. Thus, I’ve learned the only way to reach my goals is to just fiercely take chances. As Nike brilliantly says: “Just Do It”. YES.

  3. This is what I’ve told myself. The last 3 years, I’ve felt a little foolish, thinking that maybe I should go back to a 9-5 job and not take so many leaps of faith. Because my family thought I was crazy and with the amount of debt I have, I needed more security.

    But the only thing that feels impossible to me is NOT going after my dreams. It feels impossible to stop having goals, to stop working, to stop being passionate.

    One of my really good friends recently told me that it’s OK to have a lot of balls in the air – to try things and see what sticks. Because, honestly, my biggest fear isn’t failing or having to get a retail job to make ends meet.

    It’s running out of passion.

    • I hear ya, Berrak. I’ve been thinking about this a lot myself lately – and like you said, the most terrifying thing to me is not being able to follow my passions or go after my big dreams. More than anything, what I value about the position I’m in as an entrepreneur, is the freedom it allows me to purse what I’m most interested in. I’ve been at this for three years and I’m at the point where I can’t imagine being held back from doing just that.

      I believe life is about creating opportunities and making choices. Being able to do both, on my own terms, is what I value more than anything.

  4. I have a hard time in thinking anyone should be encouraged to risk it all and take a leap. It’s already tough enough providing for my family in my dead end job, I can’t imagine jumping ship and trying to start an entirely new career from scratch.

    It may be all wonderful to talk about “follow your passion” or “use your life experience,” but when there are people depending on you to provide food, shelter, and support, you cannot just pick up and throw away everything you’ve been toiling at for years.

    • Hi Sam. I agree with you – and I’m not at all saying you should just “take the leap” and throw caution to the wind. I think that’s what makes this situation so challenging for so many – because they can’t – because bills keep coming and there are families to consider. I’m very much a realist – but instead of accepting that things CAN’T change, I simply try to encourage (and put into practice myself) that things can change – sometimes gradually and often times “on the side” of your most important responsibilities. But the message I share here – that we’re never completely “stuck” still rings true, and I hope it’s what everyone takes away. Thanks for being here!

  5. As someone who recently had the “reset” button pushed on my life, I can very much relate to this post. Obviously not everyone is in a position where they can start over, but I feel that many of those who are, lack either the courage or the wisdom to know where to start. Everyone’s situation is different, and there is really no right or wrong answer. It’s all about taking that first step, as you said. Direction comes by moving, and through moving comes the courage to move a little further. In time we will find ourselves in a place that we never imagined we’d be. I recently blogged about rediscovering ourselves ( so this is definitely a topic that has been weighing heavily on me lately. Good post. I thoroughly enjoy reading your blog :)

    – Josh

  6. IMHO: Starting over is often confused with running away. People don’t like their job, family, life, etc. so the thought is, “what if I just started over?”
    Starting over doesn’t have to be drastic. Maybe start over with something simple, like talk to others doing your “dream job” before jumping into something new.
    Just a thought.
    Or you could just say “screw it” and by a one way ticket to paradise. :)

  7. The Skillery posted this on FB today. When not wearing pants is mentioned in the same post as a picture of an NES system, I’m naturally going to read it. Also, I’ve been particularly hard on myself lately as I’m considerably “unsuccessful” at life (by my own definition). So I enjoyed reading this. And that you’re a fellow Nashvillian just makes it that much better.

  8. It is so inspiring and affirming to see/read your posture on Starting Over and all that it takes in (and leaves out – like ‘old weight’). I decided to do that when I retired a tad early from Congressional service (servitude?) for Members o the House and Senate. No, truly it was a massive, challenging and exciting growth experience that exposed me to world leaders, entertainment corporate moguls, actors, recording industry executives, civic leaders, civil rights leaders, events, places and operational tasks of high level on an everyday basis that I would never have experienced in any other field. Moreover, it drew out capabilities I never knew I had, and in the end opened my eyes/expanded my vision for greater potential in my own life. I did not want to work 20 years there (I did), retire, sit on a porch, then die.

    I wanted to (1) write/publish inspirational/motivational books. I wanted also to (2) start an independent advocacy service helping people whom the government wrongly denied services and benefits, and have those denials reversed. I have done (1) and (2), and now am embarking on the 3rd part of my 4-pointed goal: Public Speaking for targeted groups that almost everyone can relate to at some stage in their lives. What’s #4? The biggest and most dauntingly elusive of all. Seems unattainable at first thought. But it really is not. All it will take is the right person to hear me, see me, feel my energy and unhampered humor seasoned in the reality messages I give, and that person just might put my name in front of the right executive. That’s how I ended up working in the Clinton Administration.

    It does not matter what #4 is…what is awesome is that I have the heart and nerve to dream it at all! I call this stage of my Journey “Life: Act II” which is going to be my New Normal – finding my lane and DRIVING in it.

    Thank you for affirming that what I am striving for can be done. As you said, I made a new plan, and as I put it – I caught a new vision for my Life.

  9. Hi Matt it is embarrassing that one so young can be so bright, well done and one for your manner and attitude from what I read a good natured person.
    I can empathise with people in many of the areas you cover (now a tender 65) or 56 depends on how I wake up LOL
    I had to work at home a million years ago when war reduced the human race, being the oldest of 6 boys (then they bought a telly (black and white)thank god I could not cope with any more slaps for what the others did or did not do..
    Being the first you learned fast or died as you grow up. I went to catering college passed with flying colours and went abroad as a chef (in those days any where to parents outside Cornwall was abroad). I worked hard but always trying too hard (scarred of not being the best) so I would not end up as our parents did (mother died when I was 19 and in a
    hotel over seas! she sent me even though I would never see her again, may she rest in piece)
    Over the next 3 years I worked (hated the thought of failing) and then met a lady now my wife of 43 years.
    Now for those who dare not to dare and die old but young take heed..My wife is from Jamaica we met in Birmingham UK of course!! . Without the nitty and gritty racial problems within a year I had joined the Armed Forces (a way out initially) 22 years later a couple of active duties and the rest, we came through even managed to have a child. We had to no struggle but push ourselves, even on my many promotions you always had to look behind and further up the ladder than anyone else to prove your mettle. Since my 22 year contact ended, now remember! you now have to start a new life in civilian life,, do not ever complain feel scared or unworthy until you have spoken to a few military people that, apart from one thing they kept the likes of you me and every person in the world safe. These people have had it all done more than most of the population in 22 years or less! than most would do in there lives yet came back and conquered. You are not worthy does not fit into our lives and should not in yours!!
    Even now I keep going (with many operations to keep moving, 4 hips will do for now) if not for my benefit or yours do it for someone else.
    I have two networking businesses to help others. I do not need to but with life as it was and is now, NO ONE has time to sit and moan, hide or blame! Be yourself and get up. God made only one of you as you are unique to him and all that you see. The day you stop is the day you die, do something to make someone else smile.
    Thanks Matt I hope it was not too long

  10. I am currently starting over again rebuilding my life (if you want to read about how it is going, I am writing a blog about it at The only reason I even blog is because I lost all of my friends, not to mention my dog, my car, my house, my girlfriend, my money, and my self esteem. It took years to get to the point where I was even willing to rebuild. I don’t know how to do it, if I can do it. I am scared to be honest with you.

  11. Matt,

    Thank you for this article. It is exactly what I needed for this time in my life.
    I am 41 years old and feel like I have never reached my potential in life as it relates to my career/ purpose in life.
    I am encouraged and excited because I feel like I get to hit the reset button and start a whole new life.
    I am looking to do something totally different with my life.
    I have been in a job rut for quite the long time.
    My biggest challenge is figuring out what to do..I have thoughts and ideas but not exactly sure on which direction.