Hitting the Wall

hit-the-wallI have had so many different careers.  It is probably why I like start-ups because I am always looking to try something new and do something different.  It is also why I like real estate projects.  There is something that thrills me about the start and the growth.  In real estate, I do like closure.  In start-ups I like to opt out when the growth hits that point where the next level of growth is not as much about problem solving but a bit more like intelligent cruise control.  Not the best description but it is the time when it helps to bring in some experienced institutional investors.

This fall we took off for a blissful month.  We realized that we could take it down a notch and could still take the Wilson business on the road.  I am doing a fair amount of traveling this fall and perhaps that is why I am truly starting to hit the wall.  Maybe it is also the beginnings of seeing what life is starting to look like with our kids out of the nest.  Who knows.
Angel investing is something that many do without any involvement.  I do not think I am capable of that.  Yet in the world of angel investing you have to make a lot of bets each year for the model to work.  Maybe it makes sense to start thinking about only doing so many a year with the hopes that the ones from the year before get a little more mature.  I don’t know.  It isn’t like I am talking to all these businesses daily but I am aware of what is going on in all of them, some more than others, and of course I am always available, focused and am happy to help, talk and do whatever I can do for the entrepreneurs I have invested in. I also sit on several boards from start-up to non-profit.
The real estate is a whole other life.  One I rarely speak about but takes up a lot of space in my head.  Growing a portfolio takes time, management and obviously a lot of thought.
This past week I have been wondering am I hitting the wall?  I admit it is exciting to have built a new career and feel like I am making an impact on businesses and women.  That feels great. I have always been competitive and I always like to win but how much do I need to win?
Maybe I am describing something that many others feel but don’t talk about.  It is probably a feeling that most early stage entrepreneurs feel.  That feeling of there aren’t enough hours in the day, I won’t be able to get it all done, am I crazy to be doing all this, how do I take it down a notch, can I take it down a notch?  it feels great to be able to focus on thinking about businesses which I truly do love (start-up, real estate, and the rest) but I think that once this year ends, I am going to spend some time trying for a little more balance.
Practice what you preach, right?

Comments (Archived):

  1. Rohan

    Since I love quotes – here’s one I thought I’d share (if I haven’t before). “Life is all about the balancing, not about being balanced.”

    1. Gotham Gal

      Good one

  2. fredwilson


    1. Gotham Gal


    2. William Mougayar

      It helps you to re-focus and re-assess continuously? i’m intrigued.

    3. LE

      Meditation!!!Treating the symptoms not the cause.

    4. pointsnfigures


  3. Andrew Kennedy

    nice post.

  4. AG

    I suppose when you’re in the position of financial flexibility, the question is, when you look back in 5 or 10 or 15 years, would you be happy that you spent your time doing this as opposed to doing something else, assuming the alternative would be meaningful in its own, if different, way.

    1. Gotham Gal

      i think it is more about balance. i find what i do incredibly meaningful. it is more about play vs work balance

      1. WA

        Is it balance to be sought or is it life-play & work integration? Seems integration would allow for less of a chance of getting out of balance. Or so say the GenY’s…

        1. pointsnfigures

          I never found the line between work and play. It never seemed like work if I loved what I was doing. As I age, I am learning to be in the moment more and more. It blurs a lot of lines for me, but I am not as stressed about not “playing”. Going out to dinner becomes playing if you eat in the right places-which from your photos you do!To be honest, the hardest part about an empty nest for me are filling in the silences. My wife and I are around each other a fair amount, and sometimes when there isn’t constant conversation, it can get uncomfortable. But, it’s okay.

          1. WA

            Thanks for the open response, apologies for the delay, been on the road for a few…I agree that by loving what we do it is very rarely work. And I find it can be, at times, work – in order to accomplish doing what I love. When my wife and I work we work well together and when we play well together. We can share the feelings the joy of being alive in those moments, work or play; senses are heightened and we experience are some of the most powerful feelings of bonding, friendship and love we have together.When we first met it was evident we shared sets of values and cultural commonalities. It seems to have lent to the serenity of comfortable silences as perhaps we digested our conversation and sharing of thoughts. We have never lost that and it has only grown through the years. For me, an extrovert and type A, it was a truly tectonic shift in the foundation of a relationship. A held hand, a knowing nod, a smile of understanding. All without words.Perhaps the strength, in such silences, is that it allows the conversation and communication in our relationships to go to that part of our subconscious where it can incubate. Where those shared thoughts become the power to create things and where shared emotions help us understand it a bit better. And then the conversation starts again, and the comfortable silences are re-iterated, giving life to something new again. A pretty virutuous loop. I urge those silences to be embraced and then discussed. Venture or Angel Love so to speak…Peace and Prosperity to you and yours PnF, I always enjoy your posts here and elsewhere. GG, as always, the same to you and yours…

          2. Gotham Gal

            Thanks…. And the best to you and yours too

  5. William Mougayar

    It sounds like you have already self-prescribed what you need to do, no?

    1. Gotham Gal

      pretty much. just thinking outloud.

  6. Guest

    .I am a real estate guy. Real estate persons are builders. We get paid with the psychic currency of seeing a two dimensional set of plans become a living, breathing building. There is magic in real estate. I talk to buildings I built years ago. Here is the secret — they speak back to me and our conversations are inspiring.I was a real estate guy at age 10 when I built a dam across a creek at Camp Kilmer and flooded the entire housing complex. The MPs came and found me and I was in big, big, big trouble as the water was almost four feet deep. I only marveled as to how wonderful it all worked out. I was a builder even then.When I thought I was a badass replete with a commission in the combat engineers, jump wings, Ranger tab and other accouterments — I was in the real estate business. I was in charge of taking others’ real estate using force. I liked it then though I pretended I was a soldier. I was actually a real estate guy.Real estate is a frame of mind and it does not require continuous practice. It is episodic–other than the management of existing real estate which can be purchased from others–and can ebb and flow with your time, passion and capital.It is very diverse–high rise office buildings, suburban office buildings, office showroom/tech buildings, shopping centers, apartments, warehouses, storage and land. I have done them all and I love the renovation of old buildings more than all the others combined. Though I do like warehouses as they are so plain and appreciative of just a little attention.If you think you are crazy because you love real estate, then you have found the mother lode. It is one of the only forms of craziness that is socially acceptable. Politics? A form of craziness that is not socially acceptable.Real estate — thank God you have discovered it as it will channel and feed your craziness.Each of the attached buildings contains a bit of my soul. I talk to them regularly and I love them more than 95% of the people I know.Do not fight it.JLM.

  7. Jessica Chavarro

    There is a quote from Martin Luther King, Jr. that remind me that “hitting the wall” is part of life. We constantly change and life would’t be as exciting if everything remained the same. “If you can’t fly then run, if you can’t run then walk, if you can’t walk then crawl, but whatever you do you have to keep moving forward.”

    1. Gotham Gal

      i like that.

    2. Guy Lepage

      Great quote!

  8. Steve G

    A little off target, but you broached your real estate life: I know someone who wants to start an independent energy consulting/energy efficiency one-man firm based in CT. Seems that property owners/CFOs wanting efficiency get hung up on financing costs, and conversion rate is about 25%, so I’m not sure about profitability of this putative consulting/procurement biz. The larger 50 state independent energy consulting firms are linking up with VC-funded software platforms like Noesis.com (Austin) and utility companies and ESCOs rely on VC-funded software platforms like Retroficency for online energy audits. I wonder if this person has a prayer of building a client base, in terms of these trends….Any thoughts?

    1. Gotham Gal

      tough one

    2. LE

      I wonder if this person has a prayer of building a client base, in terms of these trends….Any thoughts?The easiest way to figure out if there is opportunity there is to have your friend knock on some doors and talk to various property managers or property management companies. It can be as simple as “I’m thinking of doing this idea do you get approached by other firms and if so have you ever considered doing this and if not why not?”. Just have a conversation without trying to sell anything. If your friend can’t get in the door doing that he won’t be able to sell later on (to the same or different people).This is actually an easy business to do (assuming the market is there of course and you can charge enough for your time) because you can simply cold call your way to customers. As far as not having experience that doesn’t matter. People will assume you are who you say you are. I’ve done this type of thing twice already, once right out of college. Nobody ever asked me to prove anything.I’m at a condo complex (not in CT) that probably could save money on energy (old inefficient lighting as an example). I know nobody has approached us since I raised the issue last year but nobody wants to do the work to evaluate our current situation. No question if you called on 10 buildings like ours you’d gain a client. If you can’t then you can’t sell or something in your marketing is off.Btw, I remember firms that did that back in the 70’s reading direct mail my dad got at his office. They would audit utility bills.

  9. Mike Hart

    It is all about finding the balance in life. As time passes we all change as does our fulcrum. Thank you for thinking out loud – it helps us all.

  10. LE

    I won’t be able to get it all done, am I crazy to be doing all this, how do I take it down a notch, can I take it down a notch? The good thing about what you are doing is you can take it down a notch. For sure. [1] And that’s coming from someone who is biased toward work and from the “school of 24×7”. I work all the time. My wife is dragging me away for my birthday I can skip that no problem. Just another day to me. I feel most comfortable at my desk in my office in front of my three large Apple displays. I travel with two laptops and 2 forms of internet access (in addition to hotel wifi). And I’m happy doing this as well.But you aren’t a 20 or 30 something business person who needs to earn a living by building a business or even a attorney building a law practice. (Neither am I by the way but we are talking about you here not me). You don’t need the money. You (and Fred) are doing what you do for other reasons. You aren’t trying to build a business so you can eventually buy a resort home and retire. Or be able to send your kids to a good school and/or pay for their college. Or to live comfortably and travel. And so on. You are there now.That said I think that the issue with both you and Fred (and I’ve said this before) is to continue to stay “relevant”. In order to stay relevant you will definitely need to continue working and doing what you are doing. But can you cut back, sure? Should you? Sure you asked the question so you must be suffering the effects and your body is talking to you.[1] I used to get into this fight with my inlaws all the time. I said with what I did I couldn’t just dial it back. I said “I’m not working at a job where I get paid $x and can decide to work y less hours. I don’t know (as I like to say) ‘the thing that will lead to the thing'”. I have to work as much as I possibly can since I don’t know exactly how secure what I am doing is or when the business climate will change and things won’t be the same.

  11. Charlene Ngamwajasat MD

    I think taking time off here and there is a great idea. Also daily time outs. Meditation or yoga can be helpful because of stress reduction, mindfulness and it’s a set time to focus on YOU. If you’re not used to it, can be hard at first but well worth it. Or since you seem technically inclined maybe try something like the Muse headband (or something like it). I’m not affiliated with them but recently saw a demo, understand the cognitive behavioral biofeedback science it’s based on, and liked the wind component (basically it uses EEG tech and can sense when your mind is really active & so you hear the sound of wind blowing and the wind dies down as you focus & go deeper into meditation.) There’s also a sect of meditation where you don’t even have to sit still, it can be doing a task or even just walking, but doing so mindfully. Having worked in various hospitals, including critical care, oncology, and palliative care units, I’ve had the privilege of taking care of people and we’d often have conversations related to life. Looking back on life, regardless of whether they were 25 or 85, what people were most proud of were their families. What they regretted wasn’t working more but not working less, not traveling, not spending more time on themselves or with their friends and family. I think it’s great you’re working towards balance.

  12. Steven Kane

    it can be very liberating to try to enjoy playing but letting go of need to win. its a luxury, enjoy it