When Is It Time To Lead Again?

I received this fantastic question recently through my blog:

Hey Chris, 

I’m a big fan of your work with Dave Ramsey and love the EntreLeadership Podcast. Thank you for delivering such valuable insight on business and leadership.

I used to own my own business. But after taking a few steps back, I realized how many mistakes I made, from financial to hiring and firing to consistently leading my team to become true “owners” of their positions.

I’ve spent the last few years re-learning leadership, rebuilding trust with my family and developing my leadership skills by learning to be led. How do you know when you are prepared to forgive yourself for past mistakes and lead again? 

Thanks, Chris! God Bless.

First, I have to congratulate you on understanding that you might not have been the best leader. All leaders, and I mean ALL leaders, have to understand they have areas where they struggle. Being willing to actually face and fix those areas is a sign of a true leader.

Don’t look at this as a “twelve-step program to leading again. Instead, understand that as a leader it’s your job to make your team successful, not the other way around. click to Tweet

You seem to get this concept, so I definitely think you’re ready to lead again. But also know that beating yourself up over past mistakes is a waste of time. Learn from the past and move on.

No leader can be great if they can’t get over themselves. If it’s still an issue with you, then make sure you are sitting down with a great coach or counselor to get it all worked out.

Question: What would you tell our friend?



Walk through your challenges with one of our coaches for FREE and see the difference a shift in mindset can make. 


Get more out of your business, your team, and yourself than you thought possible. Sign up to get free leadership tips and advice today.

Check Our Podcast


Sign up for weekly curated insights and frameworks from coaches, leaders, and business owners that help you take your business to the next level.

Posted in

Meet Chris LoCurto


Chris has a heart for changing lives by helping people discover the life and business they really want.

Decades of personal and leadership development experience, as well as running multi-million dollar businesses, has made him an expert in life and business coaching. personality types, and communication styles.

Growing up in a small logging town near Lake Tahoe, California, Chris learned a strong work ethic at home from his full-time working mom. He began his leadership and training career in the corporate world, starting but at E'TRADE.

66 thoughts on “When Is It Time To Lead Again?”

  1. Man, not beating yourself up is tough! Certainly a weakness of mine! My initial thought was this person needs to read Matt McWilliams’ blog(www.MattMcWilliams.com)! Matt is an awesome example of a transparent leader who has recognized, admitted, and fixed many of the things he did as a leader and used those former weaknesses to teach and build others. (btw, that was not a paid endorsement, but I won’t refuse any compensation you wanna send my way Matt!)
    Beyond that, I think you’re right Chris, if you’re heart is in the right place and you’re working to be better those are qualities that will make people WANT to follow you, which is really the only way you can lead!

    1. Nice point Joel – like it or not, if you have a fam – you don’t have the option of retreat. You get to lead every time you roll outta bed each day. (Sometimes even while under the covers…there is no stopping it!)

  2. Seems like it’s time. Spending a couple year soul searching and learning from mistakes is a great place to start. I would think that over time and through connections, you’ll be put to the test and that will bring out whether you are truly ready or not.

    My guess, you are.

      1. Wanting
        to lead is definitely a start, but it can never be an excuse for allowing bad
        habits to perpetuate. You can admit you
        need better listening skills, and you can profess you understand that a “C”
        needs to explain their thoughts, even though as a “D” you don’t want to
        hear. But for each time you cut them off
        midsentence and move onto typing while they stand there, you need to be
        observant and see the effect you are producing at that moment. I don’t
        think berating yourself is the answer; however, I think every moment can lead
        to greater growth through evaluation. In
        life when you encounter stress or frustration:
        see it, acknowledge it, and let it go to bring your focus back to your
        center- your goal, your vision (apologize if you have taken a team member off track
        with you in your actions) . Once you can
        be aware, it is easier to self -correct in each circumstance; you can stay on
        track, readily admit when you have gone astray from your path and LEAD by example
        of how in-tune you are with your own process. Once you can identify, accept,
        forgive, grow and focus internally and externally you will be leading and evolving
        into the leader your team needs- to both believe in the change that is coming
        and in the change they can make within themselves

  3. I had a disastrous introduction to leadership — I was a crew chief on a volunteer rescue squad and I still remember the peak of my leadership prowess when it came at the end of a shift as I argued with one of my crew members about something I’d done on a scene where I was acting as our lieutenant, not as our paramedic. She disagreed and as the heat escalated I ended up telling her, in effect, “Well, I told you to do that and you should’ve done it because I was your Lt. and I said so.”

    I knew immediately that I’d lost the argument but it took me a while to realize why.

    I took a long break from being a leader because I too thought I was inept at it. But by stepping out of it, I also removed myself from a lot of the learning opportunities I’d have continued to enjoy. I learned a lot by observing, but not by doing.

    Get back on the horse and start riding!

    1. Taking a long break is key, Bret. I’ve done the same at my job. I work weekends now, with the unofficial title of “leader” as dubbed by my manager. She has actually said, “you’re still a coordinator to me, even though you’re not the official Monday-Friday coordinator anymore.”

      I’m sort of leading from the sidelines, I guess you’d say, but it’s given me time to reflect on what I did wrong, and how I will do it better next time.

    2. Chris already said it, but my thought was that realizing you messed up and lost the argument MAKES you leadership material! Great leaders aren’t mistake free, they just recognize them and humbly fix them.

  4. That was awesome! Chris, I have been struggling since my return, I am so excited and trying to do so much. I find at times I may not be delivering the right message to the right people or the time is bad. How can you take stress out of the leadership meetings, whether it is with you spouse or your team? I feel calm most times but my body language is speaking or my tone, any hints?

    1. i would ask for candid feedback from one person you trust and can let you know how your message comes across. You may have expressions or gestures you may not be aware of and send a conflicting message. You may be saying, I’m open to suggestions and have your arms folded across your chest. :0)

        1. Awesome, I am not sure what happens, but I will check out toasmasters. It’s like this, I know what to do, am trying really hard to do it, but the message is getting there just not received?! I don’t want to be rude and thank you for your input but if you reply I may not get back till later b/c I have a presentation I am finishing and a CPA coming, we are converting to our new company (shhhh…yeah!) and I am overwhelmed. Thank you so much Lily!

          1. YAY!!! Just met with my fellow Toastmaster Club officers. It’s amazing how people learn to speak and lead with confidence when given the opportunity to practice in a safe environment.

          2. Cool. I need some practice. Been a long time since I spoke with frequency. I used to speak publicly 4-10 times a week when I ran for office but lately not so much. My last presentation I made rocked the roof, but the one before was an unmitigated disaster. I am hit or miss.

    2. Understand that leadership is not about you. It’s about wanting to help others. If your focus is on you, you will be stressed. If it’s on others, you will be to dialed in to think of you. Make sense?

      1. Yes! I feel like I am focusing on them and helping them but…(oh wait i get it) I just feel like when you have to start from scratch all the time it’s hard to stay positive. I guess it’s like if I am helping you then, why are you not soaking it in? I know I need help in this area…thanks Chris!

        1. Keven, this is what I immediately thought of when I read your last comment:

          Proverbs 25:15 “Through patience a ruler can be persuaded, and a gentle tongue can break a bone.”
          It can be hard to stay positive. But I think that sometimes, the leadership that matters most is careful, quiet, patient influence across years.

          I guess what I want to say, is that not all ‘powerful leadership moments’ happen in a matter of seconds.

          Leadership, as Chris so wonderfully pointed out, is never about you -it’s about helping others. Sometimes that ‘helping’ can be pretty darn slow.

          Another thought: who’s really in the ‘position of growth’ here? Is it the person you’re trying to lead – or is it really you?

          I know I’ve found that when I’m trying to ‘lead’ someone else, and I’m totally sucking at it – or it’s not going the way I thought/think it should – often times THEY aren’t the ones getting worked on. It’s actually ME.

          I wonder if there’s a different question here for you to consider: If you believe in God, maybe it could be something like: “God, what do you want me to learn about YOU, about me, and about this person that I’m not seeing. I love you and them enough to be patient for your answer.”

          Hope this helps some….

  5. I think stepping back is better than stepping away. If you don’t learn from what you did wrong, and just walk away, you’ll only repeat the same things when you are offered a leadership role again somewhere else.

    Read. Then read more. Listen to great podcasts like Chris’. Spend your time learning from those you admire, not complaining about those you despise.

    Like Chris said, getting over yourself is the hardest part. Until you can do that, you’re stuck in a rut. Joel said it best earlier in the comments, in that you need to continue on working on being the best leader you can be at work and at home.

    1. I agree, we are in a drought, no snow no mowing and all companies are struggling. I am sort of grateful for the lesson it is teaching me but it is giving me the time to work on me and the company a bit! I have been working through time traps and getting organized, which helps. I know the big lesson I got was don’t do what just showed up today but do what was planned.

    2. “Spend your time learning from those you admire, not complaining about those you despise.” That’s burnt rice man!

      All your comment is – stepping back vs stepping way. Yes, yes, yes! Leadership skills, I think anyway, develop best when you’re using them.

  6. It can be scary to jump into the leadership pool again after facing failures for whatever reason. I think it’s okay to be tentative about the re-entry, but I also think it sometimes takes a leap of faith. My best advice is to surround yourself with a couple of leadership mentors and accountability partners who can keep you in check, pray for you, and give you solid advice along the way.

  7. Balance! Some peoples mirrors are rosy, some only show nightmares. All of our mirrors are not the whole story. I have a feeling his mirror is too negative. I think its time for a third party to help see the whole truth.

  8. I’d say ditto to what the other commenters have said. I had a very similar experience. I’ve always enjoyed “telling others what to do”, which is not always a good leader’s trait. However, people do listen to me quite often and go with my wild ideas. The times where I have held “a title” are the times where my leadership has been the worst. I tried running a business and failed. I was given leadership opportunities at work and failed. I was very afraid of taking that responsibility on again. After getting immersed in the EntreLeadership world and reading like a crazy person, I’ve identified where my failures were. Most of them came from lack of experience, not from bad intentions. Now I’m back in a leadership role (without a formal title) and I’m really enjoying it. I try to catch myself when I’m quick to express my opinion and interrupt others. You will always make mistakes. Learning from them is what will make you a great leader.

          1. Did you just say that?

            Is “Little LoCurtos” a new term or one, like many, that has somehow escaped me?

            If new, sheer brilliance. I’m going shave the front part of my head now.

    1. Don’t know if you’re allowed to say ‘Ditto’ any more, but boy do I agree with the ‘you sure don’t need a title to lead’ thread.

      Titles TOTALLY mean nothing. My wife is a natural leader who hates having titles thrown her way, yet she has this ‘thing’ about her that other people love to follow. (Look at me, I’ve been following her around for 13 years. Ha.)

      But seriously…Lily, I don’t really know you, but in a way I feel like I do. I identify where your coming from.

      I have my own little trail of broken leadership moments in my past too. And going forward, I know I’ll blunder too -With, and without the official ‘leader hat’ on.

      But honestly: there is no other way to become a great leader, is there?

      It’s hard to grow when everything is going right. As Dave Ramsey says: it’s when you’re up to your eyeballs in manure that you’re at your best – because you’re getting EXPERIENCE.

      And best of all: The cool thing is that God chooses us anyway. 🙂

  9. Definitely can’t be an effective leader if you are doubting yourself. Other than coaching and/or counselling, you may need to take a couple small steps in leadership. Seeing a couple small victories can go a long way to boast a little of your confidence.

  10. The Questioner in this post might do well to separate forgiving himself from being ready to lead again. If God has forgiven him, then he is forgiven. Period. Then, all that learning, humility, waiting for growth, rebuilding will come to fruition slowly, when it is time. It isn’t something a leader pushes for – it is something he watches and prays for.

    End of sermon.

  11. I read some of the comments from kevinschumm here and what he is saying and what our friend is saying are REAL emotions. This is real stuff folks.

    This is how:

    – A divorced person feels starting to date again.
    – A mother (or father) feels with the remaining 3 children when one ran off to Vegas, got drunk, had a baby and moved into a trailer park with a guy named Snake.
    – I’ve felt a thousand times.

    I almost was going to comment on my own and suggest reading my blog next Wednesday (9/12). This isn’t a shameless plug, but what I thought was a pitiful post (meaning it was sad how bad of a leader I was) is actually a story of hope.

    Trust me, there is hope.

    I was never supposed to be a leader. But when I became one, the power was my drug. And I really sucked at it. But I did get better.

    Ultimately my suggestion:

    Read this post and the comments and form your own list. Pick something to start with and move forward.

    You ARE forgiven. That’s not from me though.

    Being a poor leader for a season of life is not a sign of weakness, incompetence, nor does it make you a failure. It means you screwed up. Once.

    Now go learn from it and be an awesome leader this time. Trust me when I say…”When you lead well for about a month, the memories of all the years you sucked will fade away.”

    1. I’m glad I commented before you… I wouldn’t have said a thing if I’d read this first! Amazing insight.
      And as far as promoting you… #Iwin 🙂

      Burnt rice all around!!

  12. Just flipped through a notepad of mine. I wrote in an odd spot as though it is supposed to stand out to me:

    God does not say we must GET forgiveness. He does say we must request it, when given, we must receive it, and we must give it.

    Friend, ask yourself for forgiveness and you have no choice but to forgive.

    Friend, give yourself forgiveness and you have no choice but to receive it.

    Friend, you must request it of yourself.

    I just realized that self-forgiveness is a never-ending loop.


  13. It is a pretty common saying that leaders need to lead with integrity. The first impression most people get with the word “integrity” involves morality, but in reality all integrity means is having your pieces together. A leader must be whole, so that s/he can lead with all their pieces.

  14. What would I say to my friend….

    – Biggie (has been mentioned VERY well already but…) Ask for forgiveness for messups, to God if was a private mess, and directly to those involved if your mistake touched others.. Then forgive yourself and “FIDO” (Forget It, Drive On.)

    – If you’re reluctant or scared of stepping into leadership again, that could be a great sign your heart is in the right place.

    – Practice for leadership by following someone. Great leaders are great followers. (Be under authority.)

    – If you have a family, as pointed out in previous comments, focus on loving them and leading them the best you can. This is always your first proving ground — and you never get a break from them.

    – No matter how ‘high up’ you go as a leader, or how much influence you earn – NEVER forget that you’re still just you.

    Wonderful post Chris!

  15. I would tell him that it sounds like he has done the right things to get to the place where he can be a great leader. Now, it’s just time to do it. Others have mentioned this – If you have truly prayed and asked for forgiveness from God, then you are forgiven. Who are we to not forgive ourselves when our Father has forgiven us? Forgive yourself but don’t forget your mistakes. Continue to learn from them and use them as lessons for others, as well.

Leave a Comment

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