The 5 Stages of (Startup) Grief

The ups and downs of running your own business

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Dinner was ready. I could hear the pots and plates banging in the kitchen. My son’s inpatient babbling carried down the hallway, and I felt that familiar wave of guilt begin to push up from deep in my stomach. I knew I should go and join the family, but I also knew that if I just got this report done I’d be able to send the invoice off to the client. Not that urgency on my end seemed to matter, they wouldn’t get around to paying me for weeks.

I’d started my own business to be able to have more freedom and flexibility to manage my own time. We had a new baby and I wanted to be able to help out when I could and be more available at short notice. The companies I’d worked for in the past had very strict, old school ideas about working hours and time in the office. It didn’t seem to matter whether I was working a solid 8 hours or surfing the web and chatting the colleagues all day. As long as I’d put on a suit and tie and suffered through my hour long commute each way, they were happy. But I wasn’t.

The idea of starting my own business had been with me for years. I’d always thought that this was when you’d truly made it. Being your own boss, working when you want, taking time off when you want, making up your own rules. Now that I’ve actually done it, I know it’s a lot more complicated than that.

Startup culture often talks about a business as ‘your baby’ or the team as ‘your family’. I get the connection. Running your own business is an emotional rollercoaster that requires so much of your life and focus, that it feels like more than just work. Oftentimes it is, because it’s not possible to keep the same level of separation as when you’re working for someone else.

With all this energy and emotion that’s involved in running your own business, I believe that like the 5 stages of grief, there are 5 stages of a startup.

1. Excitement

This is like going out on an amazing first date. You are having a great time, there are no consequences and all you can think about are the incredible possibilities that lay in front of you.

You might not even have started anything yet, things might just be in the planning phase which makes it even better. If you hate your day job, having a possible escape route provides a mental distraction that makes it so much easier to get through the days.

As the planning phase progresses, the excitement builds. You buy your domain name, get a logo done, start planning finances. If you’re going into business with someone else, you feed of each other’s energy and daydream about the day you sell for millions.

This is an incredible time. The level of optimism and freedom you feel really is something special. I still remember that feeling of sitting at my computer and realising that I was in charge of anything I wanted to do. Don’t like the wording on something, just change it. Don’t like doing that kind of work, don’t offer it as a service. Not sure about the charging structure, make it whatever you want.

For anyone that’s worked in a large organisation that takes 6 months to change the font on your business cards, it is a breath of fresh air.

2. Motivation

The planning phase is over, and you’ve launched! This thing you’ve dreamed about, maybe for years, has finally come to fruition. It’s been hard work, but you’ve done it. You have your own thing. The giddy excitement of the pre-launch phase has passed, and now you are pumped and motivated to make this business the huge success you know it can be.

For me, this phase was almost as good as the first. I’d never been motivated in such a way before and it felt healthy and right to want to work this much. It wasn’t about dragging myself to my desk every morning, it was about knowing that the hard work I put in would come directly back to me in the form of dollars in the bank. Well, that’s what I thought at the time anyway.

This enthusiasm is contagious, and often this means you’re able to get some small wins on the board quickly. A couple of clients or a few initial users makes you feel like you are on to a winner. Again, this feels amazing. I was right! My business will succeed! It’s a feedback loop that primes your motivation.

3. Monotony

Until it doesn’t. Like our first date, at some point the honeymoon period has to end. It might take 6 months, it might take 6 years, but eventually it becomes your job. Even if things are rolling along reasonably well, your processes will click into place and routine will begin to set in.

As long as the money is enough, for some people this might be ok. You can bumble along with the money trickling in, much like the day job you so desperately wanted to leave. The problem is that this isn’t the mentality for most people who start their own business. We start things with stars in our eyes and dreams of the big time.

In all honesty, if you get this far you’re actually doing well. You’ve got enough business and enough work to be able to get bored with what you’re doing. Some startups might skip this stage altogether. Either way, at some point we all end up at the next stage.

4. Struggle

This might come right after motivation. Maybe you don’t get those initial quick wins. Maybe the clients never come. Maybe you sit in front of your computer every day wracking your brains on how in the hell you are ever going to make money and why did you leave your cushy salary job. You think back to the free coffee, hours of reading the news and chatting to the accounts department. I had it so good, why did I leave that?

If you do make it to the monotony stage, for most it will come to a point where you want to go to the next level. This could mean many things but it almost always means more time and more money. Money to hire more people, buy more product or rent new office. Time to manage the people, source the product and find the office space.

It’s a risk. At the early stages this levelling up process can send a business under quickly. It’s not only the business on the line but often this is tied closely to your own finances. Maybe you’ve used personal credit cards to fund business expenses, maybe you’ve churned through savings with the expectation the business could pay you back. I know I did.

This is the make or break moment. You’ll either emerge out the other side with a bigger, better business, or be picking up the pieces of what’s left.

5. Breakthrough

This is not a self-selection story of how anyone can build a million dollar business if they just want it bad enough and work hard enough. I don’t believe that. Sometimes things work and sometimes things don’t, no matter how good you are or how hard you work.

What I do know is that there will always be a breakthrough. Sometimes this breakthrough comes in the form of that risk in the struggle period all paying off. You put it all on the line, pour in the money and the clients or users or work comes flooding in.

When it comes to your business this breakthrough period is special. It’s special because in most cases it brings you all the way back to phase 1. You are excited again, there are new and different challenges and the possibilities just open up in front of you. Hopefully, you never stop going through this cycle. You keep levelling up, growing and growing.

There is another type of breakthrough you can go through. This is a realisation that the whole thing isn’t for you. Whether it’s the time commitment, the costs, the stress or the responsibilities. For some people, it’s just not all it’s cracked up to be. This is the breakthrough I had from from starting my own business.

I realised that I could do it if I really wanted to, but that I would have to give up too much. I had a young family. I didn’t want my kids to grow up with an absentee Dad and I didn’t want to put myself or my wife through years of financial struggle on the chance of a pay off in the future.

No matter which end result you get, it is 100% worth it. Going through the process of starting your own business teaches you so much about what it really takes to be successful. It makes you wear many hats you never would get the chance to when working a 9 to 5. It helps you appreciate the positives that you get from working for an established company.

It also helps your narrow your focus on what is really important to you about work. I’ve now managed to find an employer that allows me freedom to do business in much the way I want, whilst still having the stability and security of a salary, benefits and holidays. Running my own business made me fearless and opened my eyes up to so many more possibilities.

So don’t feel like a failure if your business doesn’t work. Don’t feel like it’s wrong if you start to think it’s not for you. I am really glad I’m no longer running my own business, but I’m also really glad that at one point I did.

Financial Advisor. Aussie. Expat. Dad. If you want to learn about money, check me out on YouTube: Jason Mountford

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