Transition from entrepreneur to FIRE

[tacman1123]

I'm 55 now, self-employed most of my life. Fortunate in my early 30's to get a stock windfall that allowed me to spend the next 15 years effectively volunteering, getting contracts to cover employees by not myself (We did have one non-advocacy client that paid my salary for a few years, but it eventually downsized).

Then 2009 came and I decided to shift the focus of my efforts from advocacy to research, and re-brand my organization from a not-for-profit to a for-profit company.

Alas, my hopes for a second home run never came to fruition. What profit I made was put back into the company, building up the technology and expecting a big win when the time came to move from a handful of clients to a national market. At the end of 2017, I realized that this was unlikely to ever happen (a really hard thing for me to accept!), and that I'd be better off being grateful for the market recovery and focusing on financial independence, And that my organization was the biggest risk to my financial future, and I wasn't willing to continue spending more on it.

It's an odd feeling. My habit, for decades, is to work long hours with the expectation of a big payoff. Thirty years ago that worked, then in the advocacy projects we also had great success, albeit not financial (We provided key infrastructure to local and national groups advocating for smokefree workplace laws, including bars and restaurants).

Honestly, I'm a bit nervous about the next step. Some is financial -- every week the market goes up more than 2% I'm reminded of early 2008, and how I said to myself "This can't last". And was right -- but didn't do anything about it!

But the financial part is solvable (another thread in the money forum for that). I'm wondering what my daily life will look like without that goal-driven mindset. Or what that goal will be if it's not another "big win".

Yes, these are GREAT problems to have. I look forward to learning from this group about how others have transitioned.

Tac

[Senator]

You will likely find another endeavor that will lead to something else.

I have always run side businesses in addition to my work. Landscape/snow plowing, tavern, rental properties, Homeowners Association President, property manager, real estate sales, blog, etc. I no longer have the time to do most of them...

Your mind will be active, your body will need to be too. Start thinking "If I was not working today, what would I be doing". And go from there.

[MBAustin]

Welcome tacman! If you haven't found them already, we have a helpful list of things to think about as you prepare to make the transition to retirement:

Some Important Questions to Answer

I agree with Senator that, based on your introductory post here, you'll find something(s) to keep you engaged and active. I've had several volunteer gigs since ER that have used my skills honed over 30+ years in business in ways I would never had imagined.

Thanks for joining and we look forward to your contributions!

[Ready]

Welcome to the forum. If you're thinking about retiring, or at least doing work that does not generate income, it may be time to look at your asset allocation. You may want to reduce your equity exposure and lock in some of the great profits from this bull market so that you don't have to worry about a major correction wiping out a substantial amount of your portfolio.

Entrepreneurs often find traditional retirement difficult because they love doing creative things, and find relaxation to be tedious. I suspect you will figure out what the next big thing you want to do is once you make some decisions about your business. Having options is great, and it looks like you have quite a few.

[jetpack]

You selling the business or just shutting it down? I'm in a similar place, FI, but having a hard time walking away from my business. I can only sell it for a fraction of what I think it's worth...

[kcowan]

I would encourage you not to volunteer your skills for anybody. Volunteers get lumped into the same category and there is little differentiation. Look for something where you can really shine. Been there and done that. Volunteer to be president of an organization in trouble and then kick *ass! When things are fine then move on.

[phil1ben]

I was in a similar position in early 2016 and started a thread to that effect. See:

http://www.early-retirement.org/foru...ess-80699.html

Finally did sell the firm in July, 2016 and have posted 4-5 updates since then. Might be interesting to you.

[tacman1123]

Quote:

Originally Posted by jetpack You selling the business or just shutting it down? I'm in a similar place, FI, but having a hard time walking away from my business. I can only sell it for a fraction of what I think it's worth...

Alas, walking away. If the business were viable enough to sell, I'd stay with it -- I enjoyed working on the project, possibly enough to keep it as a hobby, but not enough to spend what I had been spending on it once we finished the project with my primary client. Too dependent on a small client base.

[OHjosh]

After 30 years in w*rk world, ten as a consultant in private practice, I feel your post. I've been truly retired now for about six months. I have found it to be a big change in being more than doing. Amongst the great (even wow) experiences of retirement, I have had grief for the loss of my w*rk life, including periods of depression.

At Christmas I was gifted with a great book called Transitions by William Bridges. That book talks about the thoughts, feelings and to some extent techniques people use to move through any life change: 1) reacting to the ending, 2) living through a neutral zone where you let go of what ended and prepare yourself for the new, and 3) the perception and movement into the new.

While as many posters say here, "you will find something new and wonder why you w*rked so hard", for many (at least for me) it is a process.

[tacman1123]

Quote:

Originally Posted by OHjosh Amongst the great (even wow) experiences of retirement, I have had grief for the loss of my w*rk life, including periods of depression...While as many posters say here, "you will find something new and wonder why you w*rked so hard", for many (at least for me) it is a process.

Thanks -- it's something I need to be conscious of, even prepare for.

For me, it's undoubtedly the loss of being part of a team that's working collectively toward a goal. While there are plenty of personal goals I can pursue (travel more, become a photographer, cook, learn new languages, etc.) none of those have ever been as exciting as releasing a new product or celebrating a legislative victory.